61:
468:
319:
27:
47:
1098:
2131:-Methionine is sometimes given as a supplement to dogs; It helps reduce the chances of kidney stones in dogs. Methionine is also known to increase the urinary excretion of quinidine by acidifying the urine. Aminoglycoside antibiotics used to treat urinary tract infections work best in alkaline conditions, and urinary acidification from using methionine can reduce its effectiveness. If a dog is on a diet that acidifies the urine, methionine should not be used.
1170:
3452:
1462:
1651:
1256:
and a limited number of other organisms, succinate is used. The enzyme that catalyses the reaction is MetA and the specificity for acetyl-CoA and succinyl-CoA is dictated by a single residue. The physiological basis for the preference of acetyl-CoA or succinyl-CoA is unknown, but such alternative
972:, a straight hydrocarbon sidechain amino acid which lacks the thioether. It has been conjectured that norleucine was present in early versions of the genetic code, but methionine intruded into the final version of the genetic code due to the fact it is used in the cofactor
963:), methionine residues do not have a catalytic role. This is in contrast to cysteine residues, where the thiol group has a catalytic role in many proteins. The thioether within methionine does however have a minor structural role due to the stability effect of
1362:
Cysteine is similarly produced, namely it can be made from an activated serine and either from homocysteine ("reverse transsulfurylation route") or from hydrogen sulfide ("direct sulfurylation route"); the activated serine is generally
967:
between the side chain sulfur atom and aromatic amino acids in one-third of all known protein structures. This lack of a strong role is reflected in experiments where little effect is seen in proteins where methionine is replaced by
1157:-adenosylhomocysteine is obtained. In bacteria, this is either regenerated by methylation or is salvaged by removing the adenine and the homocysteine, leaving the compound dihydroxypentandione to spontaneously convert into
2661:
Muramatsu T, Nishikawa K, Nemoto F, Kuchino Y, Nishimura S, Miyazawa T, Yokoyama S (November 1988). "Codon and amino-acid specificities of a transfer RNA are both converted by a single post-transcriptional modification".
1555:(E.C.2.1.1.5, BHMT). BHMT makes up to 1.5% of all the soluble protein of the liver, and recent evidence suggests that it may have a greater influence on methionine and homocysteine homeostasis than methionine synthase.
1231:
with pyruvate. Homoserine is the branching point with the threonine pathway, where instead it is isomerised after activating the terminal hydroxyl with phosphate (also used for methionine biosynthesis in
2497:
Cirino PC, Tang Y, Takahashi K, Tirrell DA, Arnold FH (September 2003). "Global incorporation of norleucine in place of methionine in cytochrome P450 BM-3 heme domain increases peroxygenase activity".
2853:
Navik U, Sheth VG, Khurana A, Jawalekar SS, Allawadhi P, Gaddam RR, Bhatti JS, Tikoo K. (2021). "Methionine as a double-edged sword in health and disease: Current perspective and future challenges".
2626:
Ikeuchi Y, Kimura S, Numata T, Nakamura D, Yokogawa T, Ogata T, Wada T, Suzuki T, Suzuki T (April 2010). "Agmatine-conjugated cytidine in a tRNA anticodon is essential for AUA decoding in archaea".
1334:
If it reacts with methanethiol, it produces methionine directly. Methanethiol is a byproduct of catabolic pathway of certain compounds, therefore this route is more uncommon.
4454:
1607:
2540:
Alvarez-Carreño C, Becerra A, Lazcano A (October 2013). "Norvaline and norleucine may have been more abundant protein components during early stages of cell evolution".
4578:
1183:
in humans and other animals, which must ingest methionine or methionine-containing proteins. In plants and microorganisms, methionine biosynthesis belongs to the
3239:
664:
2920:
Cavuoto P, Fenech MF (2012). "A review of methionine dependency and the role of methionine restriction in cancer growth control and life-span extension".
964:
3408:
4447:
2780:
2955:
Cellarier E, Durando X, Vasson MP, Farges MC, Demiden A, Maurizis JC, Madelmont JC, Chollet P (2003). "Methionine dependency and cancer treatment".
2888:
1313:
1275:
956:
1734:
There is inconclusive clinical evidence on methionin supplementation. Dietary restriction of methionine can lead to bone-related disorders.
4440:
1445:
1266:
The hydroxyl activating group is then replaced with cysteine, methanethiol, or hydrogen sulfide. A replacement reaction is technically a γ-
521:
2902:
2392:"Redox modulation of cellular signaling and metabolism through reversible oxidation of methionine sensors in calcium regulatory proteins"
1671:
172:
2264:
2238:
1227:
series). The intermediate aspartate semialdehyde is the branching point with the lysine biosynthetic pathway, where it is instead
808:, methionine plays a critical role in the metabolism and health of many species, including humans. Methionine is also involved in
3401:
1241:
In most organisms, an acetyl group is used to activate the homoserine. This can be catalysed in bacteria by an enzyme encoded by
3701:
1552:
4649:
4398:
3082:
3014:
1129:
donor. SAM-e is composed of an adenosyl molecule (via 5′ carbon) attached to the sulfur of methionine, therefore making it a
1714:
methionine can also be synthesized from diethyl sodium phthalimidomalonate by alkylation with chloroethylmethylsulfide (ClCH
1019:, the codon AUA also encodes for methionine. In the standard genetic code AUA codes for isoleucine and the respective tRNA (
4962:
4553:
2041:
High levels of methionine can be found in eggs, meat, and fish; sesame seeds, Brazil nuts, and some other plant seeds; and
1408:
2283:
1141:-methyl group to be transferred to an oxygen, nitrogen, or aromatic system, often with the aid of other cofactors such as
4558:
3765:
5216:
3394:
2852:
2797:
2778:
Karlheinz Drauz; Ian
Grayson; Axel Kleemann; Hans-Peter Krimmer; Wolfgang Leuchtenberger; Christoph Weckbecker (2006).
3100:"Senile hair graying: H2O2-mediated oxidative stress affects human hair color by blunting methionine sulfoxide repair"
2221:
482:
160:
1007:, encoded by UGG, is the other). In reflection to the evolutionary origin of its codon, the other AUN codons encode
4415:
4174:
2999:
Dietary
Reference Intakes for Energy, Carbohydrates, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids
2341:"Amino acids biosynthesis and nitrogen assimilation pathways: a great genomic deletion during eukaryotes evolution"
2170:
724:
26:
5221:
4784:
4297:
3075:
The
Consumer's Guide to Dog Food: What's in Dog Food, Why It's There and How to Choose the Best Food for Your Dog
1067:
5236:
1485:
1441:
1764:
in 2002. For methionine combined with cysteine, for adults 19 years and older, 19 mg/kg body weight/day.
1760:
The Food and
Nutrition Board of the U.S. Institute of Medicine set Recommended Dietary Allowances (RDAs) for
4813:
2049:, though protein dense, are low in methionine. Proteins without adequate methionine are not considered to be
1418:
1012:
1238:
In plants and possibly in some bacteria, phosphate is used. This step is shared with threonine biosynthesis.
4943:
3691:
2081:, thereby promoting antioxidant-mediated cell defense and redox regulation. It also protects cells against
1469:
Although mammals cannot synthesize methionine, they can still use it in a variety of biochemical pathways:
1016:
407:
314:
5226:
5121:
4654:
3999:
445:
1568:
1427:
1359:", while the pathway using hydrogen sulfide (or methanethiol) is called "direct-sulfurylation pathway".
1294:
1223:
by two reduction steps of the terminal carboxyl group (homoserine has therefore a γ-hydroxyl, hence the
238:
5211:
2165:
827:
AUG. It was named by Satoru Odake in 1925, as an abbreviation of its structural description 2-amino-4-(
640:
2134:
Methionine is allowed as a supplement to organic poultry feed under the US certified organic program.
2077:
effectiveness, and a gradual loss of hair color. Methionine raises the intracellular concentration of
1011:, which is also a hydrophobic amino acid. In the mitochondrial genome of several organisms, including
890:
form under biological pH conditions) located in α-position with respect to the carboxyl group, and an
5010:
4918:
4644:
4568:
4350:
4207:
3899:
3475:
326:
4593:
5131:
4938:
4794:
4573:
3417:
1413:
1390:
1356:
1047:
952:
463:
3169:-dopa and sulfur-containing antioxidants: new pharmacological tools against Parkinson's disease".
1600:
1588:
1432:
1302:
4977:
4933:
4761:
4534:
4403:
4127:
3846:
3758:
1529:
1381:-phosphoserine is used. CysK and CysM are homologues, but belong to the PLP fold type III clade.
1122:
4432:
812:
and various processes related to DNA transcription, epigenetic expression, and gene regulation.
5186:
5065:
5042:
4880:
4789:
4716:
4621:
4509:
4469:
4377:
4343:
3711:
1682:
1506:
1496:
1196:
1038:
The methionine codon AUG is also the most common start codon. A "Start" codon is message for a
709:
5002:
4678:
4233:
4145:
3706:
3696:
3204:
Refsum H, Ueland PM, Nygård O, Vollset SE (1998). "Homocysteine and cardiovascular disease".
2990:
2882:
2065:
Loss of methionine has been linked to senile greying of hair. Its lack leads to a buildup of
1115:
1043:
1028:
933:
84:
1309:). Cystathionine is bound differently in the two enzymes allowing β or γ reactions to occur.
1235:
Homoserine is then activated with a phosphate, succinyl or an acetyl group on the hydroxyl.
4477:
4466:
4032:
3821:
3798:
3716:
3349:
2671:
2549:
2160:
1761:
1478:
1278:, which is a subset of the PLP-dependent fold type I clade. They utilise the cofactor PLP (
1267:
1109:
973:
960:
786:
433:
425:
417:
275:
53:
2268:
695:
685:
259:
8:
5231:
5178:
4967:
4659:
4639:
4077:
3520:
2777:
2138:
2105:
1572:
1518:
1437:
1340:
1279:
816:
267:
135:
108:
67:
3353:
2675:
2553:
2339:
Guedes RL, Prosdocimi F, Fernandes GR, Moura LK, Ribeiro HA, Ortega JM (December 2011).
2242:
1312:
If it reacts with free hydrogen sulfide, it produces homocysteine. This is catalysed by
467:
318:
217:
209:
201:
127:
119:
4588:
4372:
4282:
4218:
4058:
4021:
3751:
3467:
3375:
3313:
3147:
3111:
3098:
Wood JM, Decker H, Hartmann H, Chavan B, Rokos H, Spencer JD, et al. (July 2009).
3055:
2760:
2695:
2591:
Jukes TH (August 1973). "Arginine as an evolutionary intruder into protein synthesis".
2573:
2522:
2367:
2340:
1687:
1664:
1253:
1228:
1075:
903:
60:
3386:
2968:
2747:
2714:
1843:
5126:
5084:
4277:
4267:
4192:
4184:
4137:
4114:
4092:
3731:
3553:
3367:
3305:
3221:
3186:
3139:
3078:
3047:
3043:
3010:
2972:
2937:
2870:
2823:
2793:
2752:
2687:
2643:
2608:
2604:
2565:
2514:
2479:
2411:
2372:
2321:
2217:
2066:
1492:
1339:
If homocysteine is produced, the thiol group is methylated, yielding methionine. Two
1224:
1178:
899:
3317:
3151:
3059:
2764:
2577:
2526:
1596:
1149:
in humans). Some enzymes use SAM-e to initiate a radical reaction; these are called
4634:
4514:
4324:
4150:
4050:
3379:
3357:
3340:
3295:
3252:
3213:
3178:
3131:
3121:
3039:
3002:
2964:
2929:
2862:
2785:
2742:
2699:
2679:
2635:
2600:
2557:
2506:
2469:
2403:
2362:
2352:
2313:
2175:
2155:
2050:
1373:
1271:
1212:
750:
675:
629:
553:
32:
2789:
396:
4928:
4736:
4382:
4337:
3954:
3778:
2407:
2113:
1749:
1738:
1536:
1192:
380:
3217:
2814:
388:
46:
4923:
4563:
4524:
4409:
4331:
4272:
4243:
4167:
4081:
3944:
3787:
3653:
2933:
2357:
1853:
1677:
864:
718:
2866:
2561:
2241:. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from
5205:
5108:
5075:
5037:
4895:
4779:
4302:
4068:
3962:
3879:
3726:
3647:
3641:
3543:
2325:
2070:
2053:. For that reason, racemic methionine is sometimes added as an ingredient to
1644:
1619:
1611:
1584:
1580:
1403:
1286:
1200:
1158:
922:
618:
307:
2994:
1558:
1133:
cation (i.e., three substituents and positive charge). The sulfur acts as a
5146:
5024:
4900:
4731:
4664:
4529:
4519:
4499:
4162:
3871:
3441:
3371:
3309:
3190:
3143:
3051:
2976:
2941:
2874:
2756:
2647:
2569:
2518:
2483:
2474:
2457:
2415:
2376:
2117:
2109:
1928:
1745:
1703:
1615:
1290:
1208:
1000:
856:
820:
809:
690:
680:
670:
4583:
3225:
2691:
2612:
2301:
1767:
This translates to about 1.33 grams per day for a 70 kilogram individual.
4876:
4292:
4263:
4248:
4122:
3934:
3894:
3856:
3685:
3618:
3126:
3099:
2639:
2317:
2078:
1864:
1800:
1522:
1150:
1134:
1097:
918:
872:
805:
296:
5156:
4972:
4953:
4852:
4847:
4842:
4741:
4629:
4608:
4481:
4463:
4318:
4223:
4007:
3987:
3977:
3861:
3806:
3721:
3562:
3538:
3484:
2074:
1938:
1811:
1789:
1632:
1576:
1220:
1032:
1008:
1004:
969:
876:
852:
587:
535:
491:
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
327:
249:
167:
3182:
3135:
2510:
5056:
4872:
4837:
4770:
4756:
3972:
3929:
3914:
3884:
3831:
3612:
3577:
3567:
3528:
3362:
3335:
2683:
2150:
2093:
1896:
1832:
1707:
1344:
1184:
1142:
1130:
1059:
980:
910:
895:
3743:
3300:
3275:
2391:
717:
Except where otherwise noted, data are given for materials in their
5112:
5099:
5046:
4868:
4832:
4823:
4727:
4688:
4504:
4202:
4040:
3982:
3967:
3919:
3909:
3836:
3811:
3774:
3665:
3659:
3606:
3533:
3451:
3006:
2101:
2089:
2082:
2054:
1979:
1699:
1640:
1592:
1219:
First, aspartic acid is converted via β-aspartyl semialdehyde into
1204:
1169:
1071:
1039:
984:
944:
793:
354:
286:
3116:
3001:. Washington, DC: The National Academies Press. pp. 589–768.
1726:) followed by hydrolysis and decarboxylation. Also see Methanol.
1591:, as in the biosynthetic pathway, cystathionine is broken down to
171:
159:
4804:
4723:
4702:
4693:
4612:
4598:
4544:
4462:
4156:
4088:
3510:
3505:
3500:
3489:
3436:
3431:
2097:
1711:
1063:
1055:
979:(SAM-e). This situation is not unique and may have occurred with
926:
914:
860:
797:
608:
366:
4909:
4707:
4490:
4364:
3600:
3572:
3479:
3276:"A novel biorational pesticide: efficacy of methionine against
3030:
Finkelstein JD (May 1990). "Methionine metabolism in mammals".
2660:
2302:"On the Occurrence of a Sulphur-containing Amino acid in Yeast"
2046:
2042:
2018:
2000:
1969:
1821:
1188:
1126:
948:
228:
2338:
2137:
Methionine can be used as a nontoxic pesticide option against
1461:
1050:. As a consequence, methionine is often incorporated into the
995:
Methionine is one of only two amino acids encoded by a single
774:
3924:
2539:
2396:
Biochimica et
Biophysica Acta (BBA) - Proteins and Proteomics
2045:
grains. Most fruits and vegetables contain very little. Most
1989:
1886:
1650:
1636:
1274:. All the enzymes involved are homologues and members of the
996:
955:. Excluding the few exceptions where methionine may act as a
824:
801:
191:
148:
2954:
1737:
Methionine supplementation may benefit those suffering from
792:
As the precursor of other non-essential amino acids such as
762:
450:
2625:
2216:(62nd ed.). Boca Raton, FL: CRC Press. p. C-374.
2085:
induced nigral cell loss by binding oxidative metabolites.
2029:
1917:
1906:
1875:
1663:
The degradation of methionine is impaired in the following
1282:), which functions by stabilising carbanion intermediates.
930:
768:
765:
344:
2496:
1177:
As an essential amino acid, methionine is not synthesized
1153:
enzymes. As a result of the transfer of the methyl group,
1104:-Adenosylmethionine is a cofactor derived from methionine.
3203:
2239:"Nomenclature and Symbolism for Amino Acids and Peptides"
2196:
1959:
1948:
1559:
Reverse-transulfurylation pathway: conversion to cysteine
1323:-acetylhomoserine (thiol)-lyase. It is encoded by either
1161:, which is excreted as a waste product or quorum signal.
867:(which is in the deprotonated −COO form under biological
756:
3097:
2141:
caterpillars, which are a serious pest to orange crops.
1517:
Methionine can be regenerated from homocysteine via (4)
3416:
868:
2306:
1752:, is related to cancer growth in a number of studies.
2989:
2088:
Methionine is an intermediate in the biosynthesis of
1551:-trimethylglycine, TMG) to methionine via the enzyme
1399:
transsulfurylation route of methionine biosynthesis:
777:
771:
2197:
Dawson RM, Elliott DC, Elliott WH, Jones KM (1959).
2593:
759:
753:
2812:
1066:during translation, although it can be removed by
925:and is the first amino acid produced in a nascent
623:281 °C (538 °F; 554 K) decomposes
5203:
3273:
2289:. Washington D.C.: National Academy of Sciences.
2112:. Improper conversion of methionine can lead to
395:
387:
379:
4997:
3274:Lewis DS, Cuda JP, Stevens BR (December 2011).
3165:Pinnen F, et al. (2009). "Codrugs linking
1317:-acetylhomoserine aminocarboxypropyltransferase
1261:lysine biosynthesis and arginine biosynthesis).
501:D/L: Key: FFEARJCKVFRZRR-UHFFFAOYSA-N
134:
126:
118:
4701:
3333:
2948:
2781:Ullmann's Encyclopedia of Industrial Chemistry
2723:-serine sulfhydrylation reaction catalyzed by
2542:Origins of Life and Evolution of the Biosphere
2284:"A Biographical Memoir of John Howard Mueller"
1867:, tuna, light, canned in water, drained solids
1579:) combines homocysteine and serine to produce
1276:Cys/Met metabolism PLP-dependent enzyme family
4448:
3759:
3402:
2919:
2848:
2846:
2389:
1456:
1384:
939:
508:D: Key: FFEARJCKVFRZRR-SCSAIBSYSA-N
3334:Rudra MN, Chowdhury LM (30 September 1950).
2913:
2887:: CS1 maint: multiple names: authors list (
2712:
2455:
2281:
1535:Homocysteine can also be remethylated using
1137:(i.e., donor/electrophile) which allows the
5032:
3336:"Methionine Content of Cereals and Legumes"
3029:
1672:Combined malonic and methylmalonic aciduria
1563:Homocysteine can be converted to cysteine.
1491:SAM-e serves as a methyl donor in many (2)
1257:routes are present in some other pathways (
694:
684:
4455:
4441:
3766:
3752:
3409:
3395:
2843:
1355:The pathway using cysteine is called the "
466:
317:
274:
266:
258:
3361:
3299:
3240:Methionine for Dogs uses and Side Effects
3125:
3115:
2746:
2473:
2451:
2449:
2447:
2445:
2366:
2356:
2267:. Oxford University Press. Archived from
815:Methionine was first isolated in 1921 by
432:
424:
416:
2443:
2441:
2439:
2437:
2435:
2433:
2431:
2429:
2427:
2425:
1649:
1460:
1285:If it reacts with cysteine, it produces
1168:
1096:
921:, meaning it indicates the start of the
3032:The Journal of Nutritional Biochemistry
2983:
1792:, white, dried, powder, glucose reduced
1440:(in mammals, this step is performed by
1089:
1042:that signals the initiation of protein
1035:(archaea) to discriminate against AUG.
462:
295:
5204:
3164:
3072:
2390:Bigelow DJ, Squier TC (January 2005).
1553:betaine-homocysteine methyltransferase
838:
308:
4650:2-Amino-3-carboxymuconic semialdehyde
4436:
3773:
3747:
3390:
2713:Mino K, Ishikawa K (September 2003).
2590:
2422:
2299:
2214:CRC Handbook of Chemistry and Physics
2211:
1909:, ground, 95% lean meat / 5% fat, raw
1693:
1658:
1626:
1199:). The main backbone is derived from
1046:from mRNA when the AUG codon is in a
494:Key: FFEARJCKVFRZRR-BYPYZUCNSA-N
237:
216:
208:
200:
4963:2,3-Dihydroxy-3-methylpentanoic acid
2456:Ferla MP, Patrick WM (August 2014).
1409:Aspartate-semialdehyde dehydrogenase
851:; encoded by the codon AUG) is an α-
674:
3418:Encoded (proteinogenic) amino acids
2458:"Bacterial methionine biosynthesis"
1744:Overconsumption of methionine, the
1367:-acetylserine (via CysK or CysM in
1351:) dependent and one is independent.
1081:is used as the initial amino acid.
369:
353:
96:2-amino-4-(methylthio)butanoic acid
35:of the canonical form of methionine
13:
3263:(49): 13501–13504. March 14, 2011.
2813:Barger G, Weichselbaum TE (1934).
1770:
1729:
1698:The industrial synthesis combines
59:
45:
14:
5248:
3327:
2727:-acetylserine sulfhydrylase from
1706:, and cyanide, which affords the
1203:, while the sulfur may come from
1187:family, along with threonine and
917:, methionine is coded for by the
3450:
3278:Heraclides (Papilio) cresphontes
2499:Biotechnology and Bioengineering
1920:, ground, 96% lean / 4% fat, raw
898:side chain, classifying it as a
804:, and the important antioxidant
749:
571:
565:
25:
4785:Imidazol-4-one-5-propionic acid
3267:
3245:
3238:Grimshaw, Jane (July 25, 2011)
3232:
3197:
3158:
3091:
3077:. New York: Howell Book House.
3066:
3023:
2895:
2806:
2771:
2706:
2654:
2619:
2584:
2533:
2490:
1755:
1647:cycle or the methionine cycle.
1512:
1495:reactions, and is converted to
1164:
1068:post-translational modification
721:(at 25 °C , 100 kPa).
4599:β-Hydroxy β-methylglutaryl-CoA
4554:β-Hydroxy β-methylbutyric acid
3288:Journal of Economic Entomology
3280:, a surrogate of the invasive
3171:Journal of Medicinal Chemistry
2383:
2332:
2293:
2275:
2257:
2231:
2212:Weast, Robert C., ed. (1981).
2205:
2190:
1774:
1643:. The process is known as the
1486:methionine adenosyltransferase
1442:homocysteine methyltransferase
1084:
800:, versatile compounds such as
653:2.28 (carboxyl), 9.21 (amino)
580:
574:
559:
1:
4814:1-Pyrroline-5-carboxylic acid
4559:β-Hydroxy β-methylbutyryl-CoA
2969:10.1016/S0305-7372(03)00118-X
2790:10.1002/14356007.a02_057.pub2
2748:10.1016/S0014-5793(03)00913-X
2199:Data for Biochemical Research
2184:
2123:
2032:, brown, medium-grain, cooked
1856:, broilers or fryers, roasted
1618:in a three-step process (see
1472:
4944:2-Methyl-3-oxopropanoic acid
3284:(Lepidoptera: Papilionidae)"
3044:10.1016/0955-2863(90)90070-2
2605:10.1016/0006-291x(73)90151-4
2408:10.1016/j.bbapap.2004.09.012
1951:, whole, cooked, hard-boiled
1521:in a reaction that requires
1289:, which is cleaved to yield
16:Sulfur-containing amino acid
7:
5122:4-Hydroxyphenylpyruvic acid
4655:2-Aminomuconic semialdehyde
3282:Princeps (Papilio) demoleus
3218:10.1146/annurev.med.49.1.31
2144:
1776:Food sources of methionine
1610:converts α-ketobutyrate to
1477:Methionine is converted to
1293:. The enzymes involved are
1270:followed by a variant of a
990:
947:and methionine are the two
843:Methionine (abbreviated as
41:
10:
5253:
4998:generation of homocysteine
3476:Branched-chain amino acids
2934:10.1016/j.ctrv.2012.01.004
2838:, vol. 2, p. 384
2358:10.1186/1471-2164-12-S4-S2
2201:. Oxford: Clarendon Press.
1614:, which is metabolized to
1571:(an enzyme which requires
1457:Other biochemical pathways
1388:
1385:Transsulfurylation pathway
1114:The methionine-derivative
1107:
940:A proteinogenic amino acid
5217:Proteinogenic amino acids
5177:
5170:
5144:
5107:
5097:
5074:
5055:
4986:
4952:
4908:
4893:
4861:
4822:
4803:
4769:
4754:
4686:
4677:
4645:3-Hydroxyanthranilic acid
4607:
4543:
4489:
4476:
4393:
4363:
4351:Prednisolone/promethazine
4332:Methylthioninium chloride
4310:
4262:
4232:
4201:
4183:
4136:
4113:
4106:
4067:
4049:
4031:
4020:
3996:
3953:
3893:
3870:
3845:
3820:
3797:
3786:
3679:
3627:
3586:
3552:
3519:
3466:
3459:
3448:
3424:
3206:Annual Review of Medicine
2995:"Protein and Amino Acids"
2867:10.1016/j.arr.2021.101500
2562:10.1007/s11084-013-9344-3
2060:
953:proteinogenic amino acids
715:
708:
703:
657:
603:White crystalline powder
546:
517:
478:
101:
93:
83:
78:
40:
24:
5132:4-Maleylacetoacetic acid
4939:3-Hydroxyisobutyric acid
4795:Glutamate-1-semialdehyde
2957:Cancer Treatment Reviews
2922:Cancer Treatment Reviews
2398:(Submitted manuscript).
2282:Pappenheimer AM (1987).
2171:Photoreactive methionine
1608:α-ketoacid dehydrogenase
1583:. Instead of degrading
1569:Cystathionine-β-synthase
1428:Cystathionine-γ-synthase
1414:Homoserine dehydrogenase
1395:Enzymes involved in the
1391:Transsulfuration pathway
1357:transsulfuration pathway
1295:cystathionine-γ-synthase
1125:that serves mainly as a
1048:Kozak consensus sequence
1027:) uses the unusual base
704:Supplementary data page
4978:2-Methylacetoacetyl-CoA
4934:3-Hydroxyisobutyryl-CoA
4470:metabolic intermediates
3253:"Rules and Regulations"
2784:. Weinheim: Wiley-VCH.
2628:Nature Chemical Biology
2116:due to accumulation of
1844:Soy protein concentrate
1377:and some other archaea
1173:Methionine biosynthesis
5222:Glucogenic amino acids
5187:Cysteine sulfinic acid
5033:conversion to cysteine
4790:Formiminoglutamic acid
4717:3-Phosphoglyceric acid
4594:β-Methylglutaconyl-CoA
4344:Potassium permanganate
4000:neuromuscular blockade
2475:10.1099/mic.0.077826-0
2300:Odake, Satoru (1925).
1683:Methylmalonic acidemia
1655:
1507:Adenosylhomocysteinase
1466:
1174:
1105:
1054:-terminal position of
999:(AUG) in the standard
710:Methionine (data page)
64:
50:
5237:Essential amino acids
4919:α-Ketoisovaleric acid
4574:β-Ketoisocaproic acid
4569:α-Ketoisocaproic acid
4146:4-Dimethylaminophenol
2991:Institute of Medicine
2166:Paracetamol poisoning
1762:essential amino acids
1653:
1601:cystathionine-γ-lyase
1589:cystathionine-β-lyase
1575:, the active form of
1500:-adenosylhomocysteine
1464:
1446:betaine—homocysteine
1433:Cystathionine-β-lyase
1303:cystathionine-β-lyase
1172:
1100:
529:L: CSCC(N)C(=O)O
63:
49:
5006:-Adenosyl methionine
4589:β-Methylcrotonyl-CoA
4579:β-Ketoisocaproyl-CoA
4535:β-Hydroxybutyryl-CoA
4234:Paracetamol toxicity
4078:direct Xa inhibitors
3799:Alcohol intoxication
3127:10.1096/fj.08-125435
2640:10.1038/nchembio.323
2318:10.1271/bbb1924.1.87
2271:on January 27, 2018.
2161:Methionine oxidation
2010:Beans, pinto, cooked
1824:, Parmesan, shredded
1341:methionine synthases
1110:S-Adenosylmethionine
961:methionine sulfoxide
909:In nuclear genes of
855:that is used in the
787:essential amino acid
54:Ball-and-stick model
5179:Cysteine metabolism
4968:2-Methylbutyryl-CoA
4660:2-Aminomuconic acid
4640:3-Hydroxykynurenine
3354:1950Natur.166..568R
2676:1988Natur.336..179M
2554:2013OLEB...43..363A
2468:(Pt 8): 1571–1584.
2106:phosphatidylcholine
1777:
1573:pyridoxal phosphate
1519:methionine synthase
1482:-adenosylmethionine
1465:Fates of methionine
1438:Methionine synthase
1319:(formerly known as
1280:pyridoxal phosphate
1119:-adenosylmethionine
1093:-Adenosylmethionine
977:-adenosylmethionine
839:Biochemical details
817:John Howard Mueller
630:Solubility in water
595: g·mol
68:Space-filling model
21:
5227:Sulfur amino acids
5066:α-Ketobutyric acid
5043:α-Ketobutyric acid
4881:γ-Glutamylcysteine
4625:′-Formylkynurenine
4510:α-Aminoadipic acid
4420:Never to phase III
4217:Primary alcohols:
4175:Sodium thiosulfate
4059:Digoxin immune fab
3732:Dehydroamino acids
3692:Encoded (proteins)
3628:Negative charge (p
3587:Positive charge (p
1775:
1694:Chemical synthesis
1688:Propionic acidemia
1665:metabolic diseases
1659:Metabolic diseases
1656:
1627:Ethylene synthesis
1467:
1450:-methyltransferase
1343:are known; one is
1175:
1106:
725:Infobox references
538:: CSCC()C(=O)
65:
51:
19:
5212:Alpha-Amino acids
5199:
5198:
5195:
5194:
5166:
5165:
5140:
5139:
5127:Homogentisic acid
5093:
5092:
5085:Methylmalonyl-CoA
4889:
4888:
4750:
4749:
4673:
4672:
4430:
4429:
4359:
4358:
4193:Calcium gluconate
4185:Hydrofluoric acid
4138:Cyanide poisoning
4115:Arsenic poisoning
4102:
4101:
4016:
4015:
3741:
3740:
3702:Non-proteinogenic
3675:
3674:
3242:. critters360.com
3183:10.1021/jm801266x
3168:
3084:978-0-87605-467-3
3073:Palika L (1996).
3016:978-0-309-08525-0
2836:Collected Volumes
2824:Organic Syntheses
2722:
2670:(6195): 179–181.
2511:10.1002/bit.10718
2245:on 9 October 2008
2139:giant swallowtail
2130:
2073:, a reduction in
2067:hydrogen peroxide
2051:complete proteins
2039:
2038:
1639:for synthesis of
1493:methyltransferase
1423:-transsuccinylase
1301:in bacteria) and
1249:(not homologues).
1079:-formylmethionine
1074:, the derivative
875:(which is in the
835:)butanoic acid.
733:Chemical compound
731:
730:
446:CompTox Dashboard
336:L: 200-432-1
173:Interactive image
161:Interactive image
74:
73:
5244:
5175:
5174:
5105:
5104:
5019:
5018:
4906:
4905:
4767:
4766:
4699:
4698:
4684:
4683:
4635:Anthranilic acid
4515:2-Oxoadipic acid
4487:
4486:
4457:
4450:
4443:
4434:
4433:
4325:Potassium iodide
4151:Hydroxocobalamin
4111:
4110:
4051:Digoxin toxicity
4029:
4028:
3795:
3794:
3768:
3761:
3754:
3745:
3744:
3464:
3463:
3454:
3411:
3404:
3397:
3388:
3387:
3383:
3365:
3363:10.1038/166568a0
3322:
3321:
3303:
3294:(6): 1986–1990.
3271:
3265:
3264:
3257:Federal Register
3249:
3243:
3236:
3230:
3229:
3201:
3195:
3194:
3166:
3162:
3156:
3155:
3129:
3119:
3095:
3089:
3088:
3070:
3064:
3063:
3027:
3021:
3020:
2987:
2981:
2980:
2952:
2946:
2945:
2917:
2911:
2910:
2899:
2893:
2892:
2886:
2878:
2850:
2841:
2839:
2832:
2810:
2804:
2803:
2775:
2769:
2768:
2750:
2741:(1–3): 133–138.
2729:Aeropyrum pernix
2720:
2710:
2704:
2703:
2684:10.1038/336179a0
2658:
2652:
2651:
2623:
2617:
2616:
2588:
2582:
2581:
2548:(4–5): 363–375.
2537:
2531:
2530:
2494:
2488:
2487:
2477:
2453:
2420:
2419:
2387:
2381:
2380:
2370:
2360:
2336:
2330:
2329:
2297:
2291:
2290:
2288:
2279:
2273:
2272:
2261:
2255:
2254:
2252:
2250:
2235:
2229:
2227:
2209:
2203:
2202:
2194:
2156:Formylmethionine
2128:
1778:
1739:copper poisoning
1635:is also used by
1374:Aeropyrum pernix
1272:Michael addition
1213:hydrogen sulfide
1025:Escherichia coli
965:S/π interactions
889:
888:
887:
871:conditions), an
863:. It contains a
784:
783:
780:
779:
776:
773:
770:
767:
764:
761:
758:
755:
698:
688:
678:
594:
582:
576:
573:
567:
561:
554:Chemical formula
471:
470:
454:
452:
436:
428:
420:
399:
391:
383:
371:
357:
329:
321:
310:
299:
278:
270:
262:
241:
220:
212:
204:
175:
163:
138:
130:
122:
42:
33:Skeletal formula
29:
22:
18:
5252:
5251:
5247:
5246:
5245:
5243:
5242:
5241:
5202:
5201:
5200:
5191:
5162:
5136:
5089:
5070:
5051:
5016:
5015:
4982:
4948:
4929:Methacrylyl-CoA
4899:
4885:
4857:
4818:
4799:
4762:α-ketoglutarate
4760:
4746:
4737:Phosphocreatine
4706:
4692:
4669:
4603:
4539:
4472:
4461:
4431:
4426:
4425:
4410:Clinical trials
4389:
4383:Syrup of ipecac
4355:
4338:oxidizing agent
4306:
4258:
4237:(Acetaminophen)
4236:
4228:
4209:
4208:Ethylene glycol
4206:
4197:
4179:
4132:
4098:
4063:
4045:
4023:
4012:
3998:
3992:
3955:Opioid overdose
3949:
3901:
3900:Organophosphate
3898:
3889:
3866:
3848:
3841:
3823:
3816:
3789:
3782:
3772:
3742:
3737:
3736:
3717:Secondary amino
3671:
3634:
3623:
3593:
3582:
3548:
3515:
3455:
3446:
3420:
3415:
3330:
3325:
3301:10.1603/ec11132
3272:
3268:
3251:
3250:
3246:
3237:
3233:
3202:
3198:
3163:
3159:
3096:
3092:
3085:
3071:
3067:
3028:
3024:
3017:
2988:
2984:
2953:
2949:
2918:
2914:
2901:
2900:
2896:
2880:
2879:
2851:
2844:
2834:
2811:
2807:
2800:
2776:
2772:
2711:
2707:
2659:
2655:
2624:
2620:
2589:
2585:
2538:
2534:
2495:
2491:
2454:
2423:
2388:
2384:
2351:(Suppl 4): S2.
2337:
2333:
2298:
2294:
2286:
2280:
2276:
2263:
2262:
2258:
2248:
2246:
2237:
2236:
2232:
2224:
2210:
2206:
2195:
2191:
2187:
2179:-Methylcysteine
2147:
2126:
2114:atherosclerosis
2063:
1803:flour (low fat)
1773:
1771:Dietary sources
1758:
1750:DNA methylation
1732:
1730:Human nutrition
1725:
1721:
1717:
1696:
1661:
1629:
1606:(7) The enzyme
1561:
1537:glycine betaine
1526:
1515:
1484:(SAM-e) by (1)
1475:
1459:
1393:
1387:
1350:
1193:diaminopimelate
1167:
1148:
1135:soft Lewis acid
1112:
1095:
1087:
993:
942:
886:
883:
882:
881:
879:
841:
752:
748:
734:
727:
722:
667:
649:
632:
592:
579:
570:
564:
556:
542:
539:
530:
525:
524:
513:
510:
509:
503:
502:
496:
495:
492:
486:
485:
474:
455:
448:
439:
402:
372:
360:
339:
302:
281:
244:
223:
178:
152:
141:
111:
97:
89:
70:
56:
36:
30:
17:
12:
11:
5:
5250:
5240:
5239:
5234:
5229:
5224:
5219:
5214:
5197:
5196:
5193:
5192:
5190:
5189:
5183:
5181:
5172:
5168:
5167:
5164:
5163:
5161:
5160:
5151:
5149:
5142:
5141:
5138:
5137:
5135:
5134:
5129:
5124:
5118:
5116:
5102:
5095:
5094:
5091:
5090:
5088:
5087:
5081:
5079:
5072:
5071:
5069:
5068:
5062:
5060:
5053:
5052:
5050:
5049:
5040:
5028:
5027:
5022:
5008:
4993:
4991:
4984:
4983:
4981:
4980:
4975:
4970:
4965:
4959:
4957:
4950:
4949:
4947:
4946:
4941:
4936:
4931:
4926:
4924:Isobutyryl-CoA
4921:
4915:
4913:
4903:
4891:
4890:
4887:
4886:
4884:
4883:
4865:
4863:
4859:
4858:
4856:
4855:
4850:
4845:
4840:
4835:
4829:
4827:
4820:
4819:
4817:
4816:
4810:
4808:
4801:
4800:
4798:
4797:
4792:
4787:
4782:
4776:
4774:
4764:
4752:
4751:
4748:
4747:
4745:
4744:
4739:
4734:
4720:
4719:
4713:
4711:
4696:
4681:
4675:
4674:
4671:
4670:
4668:
4667:
4662:
4657:
4652:
4647:
4642:
4637:
4632:
4627:
4618:
4616:
4605:
4604:
4602:
4601:
4596:
4591:
4586:
4581:
4576:
4571:
4566:
4564:Isovaleryl-CoA
4561:
4556:
4550:
4548:
4541:
4540:
4538:
4537:
4532:
4527:
4525:Glutaconyl-CoA
4522:
4517:
4512:
4507:
4502:
4496:
4494:
4484:
4474:
4473:
4460:
4459:
4452:
4445:
4437:
4428:
4427:
4424:
4423:
4422:
4421:
4418:
4407:
4401:
4395:
4394:
4391:
4390:
4388:
4387:
4386:
4385:
4375:
4373:Copper sulfate
4369:
4367:
4361:
4360:
4357:
4356:
4354:
4353:
4348:
4347:
4346:
4334:
4329:
4328:
4327:
4314:
4312:
4308:
4307:
4305:
4300:
4295:
4290:
4288:
4287:
4286:
4280:
4275:
4260:
4259:
4257:
4256:
4251:
4246:
4244:Acetylcysteine
4240:
4238:
4230:
4229:
4227:
4226:
4221:
4214:
4212:
4199:
4198:
4196:
4195:
4189:
4187:
4181:
4180:
4178:
4177:
4172:
4171:
4170:
4168:Sodium nitrite
4165:
4153:
4148:
4142:
4140:
4134:
4133:
4131:
4130:
4125:
4119:
4117:
4108:
4104:
4103:
4100:
4099:
4097:
4096:
4085:
4082:Andexanet alfa
4073:
4071:
4069:Anticoagulants
4065:
4064:
4062:
4061:
4055:
4053:
4047:
4046:
4044:
4043:
4037:
4035:
4026:
4018:
4017:
4014:
4013:
4011:
4010:
4004:
4002:
3994:
3993:
3991:
3990:
3985:
3980:
3975:
3970:
3965:
3959:
3957:
3951:
3950:
3948:
3947:
3945:Cholinesterase
3939:
3938:
3937:
3932:
3922:
3917:
3912:
3906:
3904:
3891:
3890:
3888:
3887:
3882:
3876:
3874:
3868:
3867:
3865:
3864:
3859:
3853:
3851:
3847:Benzodiazepine
3843:
3842:
3840:
3839:
3834:
3828:
3826:
3818:
3817:
3815:
3814:
3809:
3803:
3801:
3792:
3784:
3783:
3771:
3770:
3763:
3756:
3748:
3739:
3738:
3735:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3699:
3694:
3681:
3680:
3677:
3676:
3673:
3672:
3670:
3669:
3663:
3657:
3654:Selenocysteine
3651:
3645:
3638:
3636:
3632:
3625:
3624:
3622:
3621:
3616:
3610:
3604:
3597:
3595:
3591:
3584:
3583:
3581:
3580:
3575:
3570:
3565:
3559:
3557:
3550:
3549:
3547:
3546:
3541:
3536:
3531:
3525:
3523:
3517:
3516:
3514:
3513:
3508:
3503:
3498:
3493:
3487:
3482:
3472:
3470:
3461:
3457:
3456:
3449:
3447:
3445:
3444:
3439:
3434:
3428:
3426:
3425:General topics
3422:
3421:
3414:
3413:
3406:
3399:
3391:
3385:
3384:
3329:
3328:External links
3326:
3324:
3323:
3266:
3244:
3231:
3196:
3157:
3110:(7): 2065–75.
3090:
3083:
3065:
3038:(5): 228–237.
3022:
3015:
3007:10.17226/10490
2982:
2963:(6): 489–499.
2947:
2928:(6): 726–736.
2912:
2894:
2855:Ageing Res Rev
2842:
2805:
2799:978-3527306732
2798:
2770:
2705:
2653:
2634:(4): 277–282.
2618:
2599:(3): 709–714.
2583:
2532:
2505:(6): 729–734.
2489:
2421:
2402:(2): 121–134.
2382:
2331:
2292:
2274:
2256:
2230:
2222:
2204:
2188:
2186:
2183:
2182:
2181:
2173:
2168:
2163:
2158:
2153:
2146:
2143:
2125:
2122:
2071:hair follicles
2062:
2059:
2037:
2036:
2033:
2026:
2025:
2022:
2015:
2014:
2011:
2007:
2006:
2003:
1997:
1996:
1993:
1986:
1985:
1982:
1976:
1975:
1972:
1966:
1965:
1962:
1956:
1955:
1952:
1945:
1944:
1941:
1935:
1934:
1931:
1925:
1924:
1921:
1914:
1913:
1910:
1903:
1902:
1899:
1893:
1892:
1889:
1883:
1882:
1879:
1878:, cured, dried
1872:
1871:
1868:
1861:
1860:
1857:
1850:
1849:
1846:
1840:
1839:
1836:
1829:
1828:
1825:
1818:
1817:
1814:
1808:
1807:
1804:
1797:
1796:
1793:
1786:
1785:
1782:
1772:
1769:
1757:
1754:
1731:
1728:
1723:
1719:
1715:
1695:
1692:
1691:
1690:
1685:
1680:
1678:Homocystinuria
1675:
1660:
1657:
1654:The Yang cycle
1628:
1625:
1624:
1623:
1604:
1597:α-ketobutyrate
1560:
1557:
1524:
1514:
1511:
1474:
1471:
1458:
1455:
1454:
1453:
1435:
1430:
1425:
1416:
1411:
1406:
1389:Main article:
1386:
1383:
1353:
1352:
1348:
1337:
1336:
1335:
1332:
1310:
1264:
1263:
1262:
1254:enterobacteria
1250:
1239:
1233:
1197:α-aminoadipate
1195:, but not via
1166:
1163:
1146:
1108:Main article:
1094:
1088:
1086:
1083:
1031:(bacteria) or
992:
989:
941:
938:
884:
865:carboxyl group
840:
837:
732:
729:
728:
723:
719:standard state
716:
713:
712:
706:
705:
701:
700:
668:
663:
660:
659:
655:
654:
651:
647:
637:
636:
633:
628:
625:
624:
621:
615:
614:
611:
605:
604:
601:
597:
596:
590:
584:
583:
577:
568:
562:
557:
552:
549:
548:
544:
543:
541:
540:
533:
531:
528:
520:
519:
518:
515:
514:
512:
511:
507:
506:
504:
500:
499:
497:
493:
490:
489:
481:
480:
479:
476:
475:
473:
472:
458:
456:
444:
441:
440:
438:
437:
429:
421:
412:
410:
404:
403:
401:
400:
392:
384:
375:
373:
365:
362:
361:
359:
358:
349:
347:
341:
340:
338:
337:
333:
331:
323:
322:
312:
304:
303:
301:
300:
291:
289:
283:
282:
280:
279:
271:
263:
254:
252:
246:
245:
243:
242:
233:
231:
225:
224:
222:
221:
213:
205:
196:
194:
188:
187:
184:
183:Abbreviations
180:
179:
177:
176:
164:
155:
153:
146:
143:
142:
140:
139:
131:
123:
114:
112:
107:
104:
103:
99:
98:
95:
91:
90:
87:
81:
80:
76:
75:
72:
71:
66:
57:
52:
38:
37:
31:
15:
9:
6:
4:
3:
2:
5249:
5238:
5235:
5233:
5230:
5228:
5225:
5223:
5220:
5218:
5215:
5213:
5210:
5209:
5207:
5188:
5185:
5184:
5182:
5180:
5176:
5173:
5169:
5159:
5158:
5153:
5152:
5150:
5148:
5143:
5133:
5130:
5128:
5125:
5123:
5120:
5119:
5117:
5114:
5110:
5109:phenylalanine
5106:
5103:
5101:
5096:
5086:
5083:
5082:
5080:
5077:
5076:propionyl-CoA
5073:
5067:
5064:
5063:
5061:
5058:
5054:
5048:
5044:
5041:
5039:
5038:Cystathionine
5036:
5034:
5030:
5029:
5026:
5023:
5021:
5020:-homocysteine
5013:
5009:
5007:
5005:
5001:
4999:
4995:
4994:
4992:
4989:
4985:
4979:
4976:
4974:
4971:
4969:
4966:
4964:
4961:
4960:
4958:
4955:
4951:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4916:
4914:
4911:
4907:
4904:
4902:
4897:
4896:propionyl-CoA
4892:
4882:
4878:
4874:
4870:
4867:
4866:
4864:
4860:
4854:
4851:
4849:
4846:
4844:
4841:
4839:
4836:
4834:
4831:
4830:
4828:
4825:
4821:
4815:
4812:
4811:
4809:
4806:
4802:
4796:
4793:
4791:
4788:
4786:
4783:
4781:
4780:Urocanic acid
4778:
4777:
4775:
4772:
4768:
4765:
4763:
4758:
4753:
4743:
4740:
4738:
4735:
4733:
4729:
4725:
4722:
4721:
4718:
4715:
4714:
4712:
4709:
4704:
4700:
4697:
4695:
4690:
4685:
4682:
4680:
4676:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4628:
4626:
4624:
4620:
4619:
4617:
4614:
4610:
4606:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4551:
4549:
4546:
4542:
4536:
4533:
4531:
4528:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4497:
4495:
4492:
4488:
4485:
4483:
4479:
4475:
4471:
4468:
4465:
4458:
4453:
4451:
4446:
4444:
4439:
4438:
4435:
4419:
4417:
4414:
4413:
4411:
4408:
4405:
4402:
4400:
4397:
4396:
4392:
4384:
4381:
4380:
4379:
4376:
4374:
4371:
4370:
4368:
4366:
4362:
4352:
4349:
4345:
4342:
4341:
4340:
4339:
4335:
4333:
4330:
4326:
4323:
4322:
4321:
4320:
4316:
4315:
4313:
4309:
4304:
4303:Prussian blue
4301:
4299:
4296:
4294:
4291:
4289:
4284:
4281:
4279:
4276:
4274:
4271:
4270:
4269:
4265:
4261:
4255:
4252:
4250:
4247:
4245:
4242:
4241:
4239:
4235:
4231:
4225:
4222:
4220:
4216:
4215:
4213:
4211:
4204:
4200:
4194:
4191:
4190:
4188:
4186:
4182:
4176:
4173:
4169:
4166:
4164:
4161:
4160:
4159:
4158:
4154:
4152:
4149:
4147:
4144:
4143:
4141:
4139:
4135:
4129:
4126:
4124:
4121:
4120:
4118:
4116:
4112:
4109:
4105:
4094:
4090:
4086:
4083:
4079:
4075:
4074:
4072:
4070:
4066:
4060:
4057:
4056:
4054:
4052:
4048:
4042:
4039:
4038:
4036:
4034:
4030:
4027:
4025:
4019:
4009:
4006:
4005:
4003:
4001:
3995:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3963:Diprenorphine
3961:
3960:
3958:
3956:
3952:
3946:
3943:
3940:
3936:
3933:
3931:
3928:
3927:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3907:
3905:
3903:
3896:
3892:
3886:
3883:
3881:
3880:Physostigmine
3878:
3877:
3875:
3873:
3869:
3863:
3860:
3858:
3855:
3854:
3852:
3850:
3844:
3838:
3835:
3833:
3830:
3829:
3827:
3825:
3819:
3813:
3810:
3808:
3805:
3804:
3802:
3800:
3796:
3793:
3791:
3785:
3780:
3776:
3769:
3764:
3762:
3757:
3755:
3750:
3749:
3746:
3733:
3730:
3728:
3727:D-amino acids
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3689:
3687:
3683:
3682:
3678:
3667:
3664:
3661:
3658:
3655:
3652:
3649:
3648:Glutamic acid
3646:
3643:
3642:Aspartic acid
3640:
3639:
3637:
3631:
3626:
3620:
3617:
3614:
3611:
3608:
3605:
3602:
3599:
3598:
3596:
3590:
3585:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3560:
3558:
3555:
3551:
3545:
3544:Phenylalanine
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3526:
3524:
3522:
3518:
3512:
3509:
3507:
3504:
3502:
3499:
3497:
3494:
3491:
3488:
3486:
3483:
3481:
3477:
3474:
3473:
3471:
3469:
3465:
3462:
3460:By properties
3458:
3453:
3443:
3440:
3438:
3435:
3433:
3430:
3429:
3427:
3423:
3419:
3412:
3407:
3405:
3400:
3398:
3393:
3392:
3389:
3381:
3377:
3373:
3369:
3364:
3359:
3355:
3351:
3347:
3343:
3342:
3337:
3332:
3331:
3319:
3315:
3311:
3307:
3302:
3297:
3293:
3289:
3285:
3283:
3279:
3270:
3262:
3258:
3254:
3248:
3241:
3235:
3227:
3223:
3219:
3215:
3211:
3207:
3200:
3192:
3188:
3184:
3180:
3177:(2): 559–63.
3176:
3172:
3161:
3153:
3149:
3145:
3141:
3137:
3133:
3128:
3123:
3118:
3113:
3109:
3105:
3104:FASEB Journal
3101:
3094:
3086:
3080:
3076:
3069:
3061:
3057:
3053:
3049:
3045:
3041:
3037:
3033:
3026:
3018:
3012:
3008:
3004:
3000:
2996:
2992:
2986:
2978:
2974:
2970:
2966:
2962:
2958:
2951:
2943:
2939:
2935:
2931:
2927:
2923:
2916:
2908:
2904:
2898:
2890:
2884:
2876:
2872:
2868:
2864:
2860:
2856:
2849:
2847:
2837:
2830:
2826:
2825:
2820:
2818:
2809:
2801:
2795:
2791:
2787:
2783:
2782:
2774:
2766:
2762:
2758:
2754:
2749:
2744:
2740:
2736:
2732:
2730:
2726:
2718:
2709:
2701:
2697:
2693:
2689:
2685:
2681:
2677:
2673:
2669:
2665:
2657:
2649:
2645:
2641:
2637:
2633:
2629:
2622:
2614:
2610:
2606:
2602:
2598:
2594:
2587:
2579:
2575:
2571:
2567:
2563:
2559:
2555:
2551:
2547:
2543:
2536:
2528:
2524:
2520:
2516:
2512:
2508:
2504:
2500:
2493:
2485:
2481:
2476:
2471:
2467:
2463:
2459:
2452:
2450:
2448:
2446:
2444:
2442:
2440:
2438:
2436:
2434:
2432:
2430:
2428:
2426:
2417:
2413:
2409:
2405:
2401:
2397:
2393:
2386:
2378:
2374:
2369:
2364:
2359:
2354:
2350:
2346:
2342:
2335:
2327:
2323:
2319:
2315:
2311:
2307:
2303:
2296:
2285:
2278:
2270:
2266:
2260:
2244:
2240:
2234:
2225:
2223:0-8493-0462-8
2219:
2215:
2208:
2200:
2193:
2189:
2180:
2178:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2148:
2142:
2140:
2135:
2132:
2121:
2119:
2115:
2111:
2110:phospholipids
2107:
2103:
2099:
2095:
2091:
2086:
2084:
2080:
2076:
2072:
2068:
2058:
2056:
2052:
2048:
2044:
2034:
2031:
2028:
2027:
2023:
2020:
2017:
2016:
2012:
2009:
2008:
2004:
2002:
1999:
1998:
1994:
1991:
1988:
1987:
1983:
1981:
1978:
1977:
1973:
1971:
1968:
1967:
1963:
1961:
1958:
1957:
1953:
1950:
1947:
1946:
1942:
1940:
1937:
1936:
1932:
1930:
1927:
1926:
1922:
1919:
1916:
1915:
1911:
1908:
1905:
1904:
1900:
1898:
1895:
1894:
1890:
1888:
1885:
1884:
1880:
1877:
1874:
1873:
1869:
1866:
1863:
1862:
1858:
1855:
1852:
1851:
1847:
1845:
1842:
1841:
1837:
1834:
1831:
1830:
1826:
1823:
1820:
1819:
1815:
1813:
1810:
1809:
1805:
1802:
1799:
1798:
1794:
1791:
1788:
1787:
1784:g/100 g
1783:
1780:
1779:
1768:
1765:
1763:
1753:
1751:
1747:
1742:
1740:
1735:
1727:
1713:
1709:
1705:
1701:
1689:
1686:
1684:
1681:
1679:
1676:
1673:
1670:
1669:
1668:
1666:
1652:
1648:
1646:
1642:
1638:
1634:
1622:for pathway).
1621:
1620:propionyl-CoA
1617:
1613:
1612:propionyl-CoA
1609:
1605:
1602:
1598:
1594:
1590:
1586:
1585:cystathionine
1582:
1581:cystathionine
1578:
1574:
1570:
1566:
1565:
1564:
1556:
1554:
1550:
1546:
1542:
1538:
1533:
1531:
1527:
1520:
1510:
1508:
1503:
1501:
1499:
1494:
1489:
1487:
1483:
1481:
1470:
1463:
1451:
1449:
1443:
1439:
1436:
1434:
1431:
1429:
1426:
1424:
1422:
1417:
1415:
1412:
1410:
1407:
1405:
1404:Aspartokinase
1402:
1401:
1400:
1398:
1392:
1382:
1380:
1376:
1375:
1370:
1366:
1360:
1358:
1346:
1342:
1338:
1333:
1330:
1326:
1322:
1318:
1316:
1311:
1308:
1304:
1300:
1296:
1292:
1288:
1287:cystathionine
1284:
1283:
1281:
1277:
1273:
1269:
1265:
1260:
1255:
1251:
1248:
1244:
1240:
1237:
1236:
1234:
1230:
1226:
1222:
1218:
1217:
1216:
1214:
1210:
1206:
1202:
1201:aspartic acid
1198:
1194:
1190:
1186:
1182:
1181:
1171:
1162:
1160:
1159:autoinducer-2
1156:
1152:
1151:radical SAM-e
1144:
1140:
1136:
1132:
1128:
1124:
1121:(SAM-e) is a
1120:
1118:
1111:
1103:
1099:
1092:
1082:
1080:
1078:
1073:
1069:
1065:
1061:
1057:
1053:
1049:
1045:
1041:
1036:
1034:
1030:
1026:
1022:
1018:
1014:
1010:
1006:
1002:
998:
988:
986:
982:
978:
976:
971:
966:
962:
958:
954:
950:
946:
937:
935:
932:
928:
924:
923:coding region
920:
916:
912:
907:
905:
901:
897:
893:
878:
874:
870:
866:
862:
858:
854:
850:
846:
836:
834:
830:
826:
822:
818:
813:
811:
807:
803:
799:
795:
790:
788:
782:
746:
742:
738:
726:
720:
714:
711:
707:
702:
697:
692:
687:
682:
677:
672:
669:
666:
662:
661:
658:Pharmacology
656:
652:
646:
642:
639:
638:
634:
631:
627:
626:
622:
620:
619:Melting point
617:
616:
612:
610:
607:
606:
602:
599:
598:
591:
589:
586:
585:
558:
555:
551:
550:
545:
537:
532:
527:
526:
523:
516:
505:
498:
488:
487:
484:
477:
469:
465:
464:DTXSID9020821
460:
459:
457:
447:
443:
442:
435:
430:
427:
422:
419:
414:
413:
411:
409:
406:
405:
398:
393:
390:
385:
382:
377:
376:
374:
368:
364:
363:
356:
351:
350:
348:
346:
343:
342:
335:
334:
332:
330:
325:
324:
320:
316:
313:
311:
309:ECHA InfoCard
306:
305:
298:
293:
292:
290:
288:
285:
284:
277:
272:
269:
264:
261:
256:
255:
253:
251:
248:
247:
240:
235:
234:
232:
230:
227:
226:
219:
214:
211:
206:
203:
198:
197:
195:
193:
190:
189:
185:
182:
181:
174:
169:
165:
162:
157:
156:
154:
150:
145:
144:
137:
132:
129:
124:
121:
116:
115:
113:
110:
106:
105:
100:
92:
86:
82:
77:
69:
62:
58:
55:
48:
44:
43:
39:
34:
28:
23:
5154:
5147:oxaloacetate
5031:
5025:Homocysteine
5011:
5003:
4996:
4987:
4901:succinyl-CoA
4732:Glycocyamine
4665:Glutaryl-CoA
4622:
4530:Crotonyl-CoA
4520:Glutaryl-CoA
4500:Saccharopine
4336:
4317:
4264:Toxic metals
4253:
4163:Amyl nitrite
4155:
4033:Beta blocker
3941:
3872:GHB overdose
3684:
3629:
3588:
3495:
3442:Genetic code
3348:(568): 568.
3345:
3339:
3291:
3287:
3281:
3277:
3269:
3260:
3256:
3247:
3234:
3212:(1): 31–62.
3209:
3205:
3199:
3174:
3170:
3160:
3107:
3103:
3093:
3074:
3068:
3035:
3031:
3025:
2998:
2985:
2960:
2956:
2950:
2925:
2921:
2915:
2906:
2903:"Methionine"
2897:
2883:cite journal
2858:
2854:
2835:
2828:
2822:
2819:-Methionine"
2816:
2808:
2779:
2773:
2738:
2735:FEBS Letters
2734:
2728:
2724:
2716:
2708:
2667:
2663:
2656:
2631:
2627:
2621:
2596:
2592:
2586:
2545:
2541:
2535:
2502:
2498:
2492:
2465:
2462:Microbiology
2461:
2399:
2395:
2385:
2348:
2345:BMC Genomics
2344:
2334:
2312:(8): 87–89.
2309:
2305:
2295:
2277:
2269:the original
2265:"Methionine"
2259:
2247:. Retrieved
2243:the original
2233:
2213:
2207:
2198:
2192:
2176:
2136:
2133:
2127:
2118:homocysteine
2108:, and other
2087:
2064:
2040:
1801:Sesame seeds
1766:
1759:
1756:Requirements
1746:methyl group
1743:
1736:
1733:
1704:methanethiol
1697:
1662:
1630:
1616:succinyl-CoA
1562:
1548:
1544:
1540:
1534:
1516:
1513:Regeneration
1504:
1497:
1490:
1479:
1476:
1468:
1447:
1420:
1396:
1394:
1378:
1372:
1368:
1364:
1361:
1354:
1331:in bacteria.
1328:
1324:
1320:
1314:
1306:
1298:
1297:(encoded by
1291:homocysteine
1258:
1246:
1242:
1209:methanethiol
1179:
1176:
1165:Biosynthesis
1154:
1138:
1116:
1113:
1101:
1090:
1076:
1051:
1037:
1024:
1020:
1001:genetic code
994:
974:
957:redox sensor
951:-containing
943:
908:
906:amino acid.
891:
857:biosynthesis
848:
844:
842:
832:
828:
814:
810:angiogenesis
791:
744:
740:
736:
735:
644:
102:Identifiers
94:Other names
4877:glutathione
4406:from market
4378:Ipecacuanha
4293:Dimercaprol
4249:Glutathione
4123:Dimercaprol
4022:Circulatory
3997:Reversal of
3935:Pralidoxime
3895:Nerve agent
3857:Cyprodenate
3822:Barbiturate
3722:Imino acids
3686:Amino acids
3619:Pyrrolysine
3556:, uncharged
2079:glutathione
1812:Brazil nuts
1419:Homoserine
1268:elimination
1085:Derivatives
1044:translation
934:translation
927:polypeptide
919:start codon
873:amino group
806:glutathione
789:in humans.
613:1.340 g/cm
600:Appearance
547:Properties
315:100.000.393
239:ChEMBL42336
218:CHEBI:16867
210:CHEBI:16811
202:CHEBI:16643
20:Methionine
5232:Thioethers
5206:Categories
5157:urea cycle
5014:-Adenosyl-
4988:methionine
4973:Tiglyl-CoA
4954:isoleucine
4853:Putrescine
4848:Cadaverine
4843:Citrulline
4742:Creatinine
4630:Kynurenine
4609:tryptophan
4482:acetyl-CoA
4467:metabolism
4464:Amino acid
4319:iodine-131
4254:Methionine
4224:Fomepizole
4008:Sugammadex
3988:Naltrexone
3978:Nalorphine
3862:Flumazenil
3807:Metadoxine
3712:Glucogenic
3563:Asparagine
3539:Tryptophan
3496:Methionine
3485:Isoleucine
3136:10454/6241
2861:: 101500.
2185:References
2124:Other uses
2075:tyrosinase
1939:Wheat germ
1897:chia seeds
1633:amino acid
1577:vitamin B6
1509:cysteine.
1473:Catabolism
1371:), but in
1347:(vitamin B
1221:homoserine
1145:(vitamin B
1060:eukaryotes
1033:agmatidine
1009:isoleucine
1005:tryptophan
970:norleucine
911:eukaryotes
877:protonated
853:amino acid
737:Methionine
588:Molar mass
536:Zwitterion
434:868496F25R
426:73JWT2K6T3
423:D/L:
418:AE28F7PNPL
386:D/L:
265:D/L:
250:ChemSpider
207:D/L:
168:Zwitterion
147:3D model (
125:D/L:
109:CAS Number
88:Methionine
85:IUPAC name
5057:threonine
4873:glutamate
4838:Ornithine
4771:histidine
4757:glutamate
4584:β-Leucine
4416:Phase III
4404:Withdrawn
4210:poisoning
4093:Protamine
3973:Nalmefene
3942:see also:
3930:Obidoxime
3915:Biperiden
3902:poisoning
3885:SCH-50911
3837:Ethamivan
3832:Bemegride
3775:Antidotes
3707:Ketogenic
3697:Essential
3613:Histidine
3578:Threonine
3568:Glutamine
3529:Histidine
3468:Aliphatic
3117:0706.4406
2719:-phospho-
2715:"A novel
2326:1881-1272
2151:Allantoin
2094:carnitine
2055:pet foods
1833:hemp seed
1748:donor in
1708:hydantoin
1523:vitamin B
1345:cobalamin
1229:condensed
1185:aspartate
1143:cobalamin
1131:sulfonium
981:ornithine
904:aliphatic
896:thioether
328:EC Number
5113:tyrosine
5100:fumarate
5047:Cysteine
4869:cysteine
4833:Agmatine
4824:arginine
4728:creatine
4689:pyruvate
4505:Allysine
4298:Edetates
4283:thallium
4203:Methanol
4128:Succimer
4087:against
4076:against
4041:Glucagon
3983:Naloxone
3968:Doxapram
3920:Diazepam
3910:Atropine
3849:overdose
3824:overdose
3812:Thiamine
3666:Tyrosine
3660:Cysteine
3607:Arginine
3534:Tyrosine
3521:Aromatic
3372:14780151
3318:45255198
3310:22299361
3191:19093882
3152:16069417
3144:19237503
3060:32264340
3052:15539209
2993:(2002).
2977:14585259
2942:22342103
2875:34700006
2765:28360765
2757:12965218
2648:20139989
2578:17224537
2570:24013929
2527:11380413
2519:12889037
2484:24939187
2416:15680220
2377:22369087
2145:See also
2102:lecithin
2090:cysteine
2083:dopamine
2021:, cooked
1992:, yellow
1980:Chickpea
1929:Soybeans
1835:, hulled
1700:acrolein
1674:(CMAMMA)
1641:ethylene
1599:via (6)
1593:cysteine
1530:cofactor
1232:plants).
1205:cysteine
1123:cofactor
1072:bacteria
1056:proteins
1040:ribosome
1029:lysidine
991:Encoding
985:arginine
945:Cysteine
900:nonpolar
894:-methyl
861:proteins
819:. It is
794:cysteine
785:) is an
739:(symbol
691:QG04BA90
681:QA05BA90
665:ATC code
635:Soluble
461:L:
431:D:
415:L:
394:D:
378:L:
352:L:
294:L:
287:DrugBank
273:D:
257:L:
236:L:
215:D:
199:L:
158:L:
136:348-67-4
133:D:
117:L:
4805:proline
4724:glycine
4703:glycine
4694:citrate
4613:alanine
4545:leucine
4278:mercury
4268:cadmium
4219:Ethanol
4157:nitrite
4089:heparin
3788:Nervous
3668:(≈10.1)
3609:(≈12.5)
3603:(≈10.8)
3511:Glycine
3506:Proline
3501:Alanine
3490:Leucine
3437:Peptide
3432:Protein
3380:3026278
3350:Bibcode
3226:9509248
2700:4371485
2692:3054566
2672:Bibcode
2613:4731949
2550:Bibcode
2368:3287585
2249:5 March
2098:taurine
2047:legumes
2019:Lentils
2001:Almonds
1970:Peanuts
1854:Chicken
1712:Racemic
1502:(SAH).
1397:E. coli
1369:E. coli
1180:de novo
1064:archaea
1013:metazoa
929:during
915:Archaea
913:and in
823:by the
821:encoded
798:taurine
693: (
683: (
679:)
673: (
671:V03AB26
641:Acidity
609:Density
367:PubChem
297:DB00134
186:Met, M
170::
128:59-51-8
120:63-68-3
4910:valine
4708:serine
4491:lysine
4399:WHO-EM
4365:Emetic
4024:system
3925:Oximes
3790:system
3662:(≈8.3)
3656:(≈5.4)
3650:(≈4.1)
3644:(≈3.9)
3615:(≈6.1)
3601:Lysine
3573:Serine
3480:Valine
3378:
3370:
3341:Nature
3316:
3308:
3224:
3189:
3150:
3142:
3081:
3058:
3050:
3013:
2975:
2940:
2873:
2796:
2763:
2755:
2698:
2690:
2664:Nature
2646:
2611:
2576:
2568:
2525:
2517:
2482:
2414:
2375:
2365:
2324:
2220:
2061:Health
2043:cereal
2035:0.052
2024:0.077
2013:0.117
2005:0.151
1995:0.197
1984:0.253
1974:0.309
1964:0.312
1954:0.392
1943:0.456
1933:0.547
1923:0.564
1912:0.565
1901:0.588
1891:0.593
1881:0.749
1870:0.755
1859:0.801
1848:0.814
1838:0.933
1827:1.114
1822:Cheese
1816:1.124
1806:1.656
1795:3.204
1637:plants
1189:lysine
1127:methyl
959:(e.g.,
949:sulfur
593:149.21
522:SMILES
355:C00073
229:ChEMBL
79:Names
5171:Other
4862:other
4311:Other
4107:Other
3779:V03AB
3688:types
3554:Polar
3376:S2CID
3314:S2CID
3148:S2CID
3112:arXiv
3056:S2CID
2907:WebMD
2761:S2CID
2696:S2CID
2574:S2CID
2523:S2CID
2287:(PDF)
1887:Bacon
1781:Food
1631:This
1528:as a
1225:homo-
1211:, or
1191:(via
1070:. In
1017:yeast
997:codon
825:codon
802:SAM-e
483:InChI
397:84815
276:76512
192:ChEBI
149:JSmol
5155:see
4273:lead
3368:PMID
3306:PMID
3222:PMID
3187:PMID
3140:PMID
3079:ISBN
3048:PMID
3011:ISBN
2973:PMID
2938:PMID
2889:link
2871:PMID
2831:: 58
2794:ISBN
2753:PMID
2688:PMID
2644:PMID
2609:PMID
2566:PMID
2515:PMID
2480:PMID
2412:PMID
2400:1703
2373:PMID
2322:ISSN
2251:2018
2218:ISBN
2030:Rice
1990:Corn
1918:Pork
1907:Beef
1876:Beef
1865:Fish
1645:Yang
1595:and
1587:via
1567:(5)
1505:(3)
1329:metZ
1325:metY
1307:metC
1299:metB
1259:e.g.
1247:metA
1243:metX
1062:and
1021:ileX
1015:and
983:and
931:mRNA
829:meth
796:and
408:UNII
381:6137
345:KEGG
260:5907
3358:doi
3346:166
3296:doi
3292:104
3214:doi
3179:doi
3132:hdl
3122:doi
3040:doi
3003:doi
2965:doi
2930:doi
2863:doi
2786:doi
2743:doi
2739:551
2731:K1"
2680:doi
2668:336
2636:doi
2601:doi
2558:doi
2507:doi
2470:doi
2466:160
2404:doi
2363:PMC
2353:doi
2314:doi
2069:in
1960:Oat
1949:Egg
1790:Egg
1722:SCH
1444:or
1327:or
1252:In
1245:or
1058:in
1023:in
880:−NH
859:of
847:or
845:Met
833:hio
831:ylt
747:) (
743:or
741:Met
696:WHO
689:),
686:WHO
676:WHO
451:EPA
389:876
370:CID
268:853
5208::
5145:G→
5098:G→
5045:+
4894:G→
4879::
4755:G→
4730::
4691:→
4687:G→
4412::
3690::
3374:.
3366:.
3356:.
3344:.
3338:.
3312:.
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3290:.
3286:.
3261:76
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2120:.
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2100:,
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2092:,
2057:.
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1710:.
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1667::
1532:.
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902:,
869:pH
775:iː
766:aɪ
699:)
650:)
643:(p
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534:L
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5115:→
5111:→
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5035::
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5004:S
5000::
4990:→
4956:→
4912:→
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4871:+
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4623:N
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4478:K
4456:e
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4442:v
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4266:(
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4091:(
4084:)
4080:(
3897:/
3781:)
3777:(
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3352::
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3228:.
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763:θ
760:ˈ
757:ɪ
754:m
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648:a
645:K
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575:O
572:N
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449:(
151:)
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