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N-Formylmethionine: Difference between revisions

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journal =Nature | date=Mar 4, 2010 | volume = 464 | issue = 7285 | pages = 104–107 | doi=10.1038/nature08780 | pmid=20203610 | pmc=2843437 | vauthors=Zhang Q, Raoof M, Chen Y, Sumi Y, Sursal T, Junger W, Brohi K, Itagaki K, Hauser CJ| bibcode =2010Natur.464..104Z }}</ref> Instead, fMet-containing ]s and proteins appear to be released by the mitochondria of damaged tissues as well as by damaged bacteria, and can thus qualify as an "alarm" signal, as discussed in the ] of immunity. The prototypical fMet-containing oligopeptide is ] (FMLP) which activates leukocytes and other cell types by binding with these cells' ] (FPR1) and ] (FPR2) ] (see also ]). Acting through these receptors, the fMet-containing oligopeptides and proteins are part of the ]; they function to initiate acute ] responses but under other conditions function to inhibit and resolve these responses. fMet-containing oligopeptides and proteins also function in other physiological and pathological responses.
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degrees of residual ability to start protein synthesis. ''E. coli'', ''S. pneumoniae'' and ''B. subtilis'' show almost no remaining translation ability, while ''P. aeruginosa'', ''S. aureus'','' H. influenzae'', and possibly ''S. faecalis'' still churn out plenty of protein. In ''P. aeruginosa'', this ability is facilitated by ], which can carry both Met-tRNA<sup>fMet</sup> and fMet-tRNA<sup>fMet</sup> to the ribosome.<ref>{{cite journal |last1=Piatkov |first1=KI |last2=Vu |first2=TT |last3=Hwang |first3=CS |last4=Varshavsky |first4=A |title=Formyl-methionine as a degradation signal at the N-termini of bacterial proteins. |journal=Microbial Cell (Graz, Austria) |date=2015 |volume=2 |issue=10 |pages=376–393 |doi=10.15698/mic2015.10.231 |pmid=26866044 |doi-access=free|pmc=4745127 }}</ref>
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fMet-tRNA<sub>i</sub>, which can be used by cytosolic ribosomes to produce proteins with a N-terminal fMet. These proteins are targeted for degredagtion by specific processes in the cell.<ref name=degron>{{cite journal |last1=Varshavsky |first1=Alexander |title=N-degron and C-degron pathways of protein degradation |journal=Proceedings of the National Academy of Sciences |date=8 January 2019 |volume=116 |issue=2 |pages=358–366 |doi=10.1073/pnas.1816596116 |doi-access=free |pmid=30622213 |pmc=6329975|bibcode=2019PNAS..116..358V }}</ref>
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journal |last1=Shetty |first1=S |last2=Shah |first2=RA |last3=Chembazhi |first3=UV |last4=Sah |first4=S |last5=Varshney |first5=U |title=Two highly conserved features of bacterial initiator tRNAs license them to pass through distinct checkpoints in translation initiation. |journal=Nucleic Acids Research |date=28 February 2017 |volume=45 |issue=4 |pages=2040–2050 |doi=10.1093/nar/gkw854 |pmid=28204695 |pmc=5389676}}</ref>
1609:, and use them to initiate ].<ref>{{GeorgiaImmunology|1/phagstep}}</ref><ref name="urlThe Innate Immune System">{{cite web |url=http://student.ccbcmd.edu/courses/bio141/lecguide/unit4/innate/prr.html |title=The Innate Immune System: Pattern-Recognition Receptors, Antigen-Nonspecific Antimicrobial Body Molecules, and Cytokines | 1660:].<ref>{{GeorgiaImmunology|1/phagstep}}</ref><ref name="urlThe Innate Immune System">{{cite web |url=http://student.ccbcmd.edu/courses/bio141/lecguide/unit4/innate/prr.html |title=The Innate Immune System: Pattern-Recognition Receptors, Antigen-Nonspecific Antimicrobial Body Molecules, and Cytokines | 1408:
Unexpectedly, formyltransferase can also act upon eukaryotic initiator tRNA in living yeast cells. Even under normal conditions, the nuclear-encoded formyltransferase is not completely imported into mitochondria; even more is left in the cytosol under stress. These cytosolic formyltransferase produce
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fMet is required for efficient initiaiton of protein synthesis in most groups of bacteria. The 30S ribosome&ndash;mRNA complex specifically recruits tRNAs with a formylated amino acid &ndash; tRNA<sup>fMet</sup> attached to fMet in the natural case.<ref name=p28204695>{{cite
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Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per
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fMet is coded by the same ] as methionine, AUG. However, AUG is also the ] initiation codon. When the codon is used for initiation, fMet is used instead of methionine, thereby forming the first amino acid of the nascent ] chain. When the same codon appears later in the ], normal methionine is used.
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The ] of ] cells, including those of humans, and the ] of ] cells also initiate protein synthesis with fMet. Given that mitochondria and chloroplasts have this initial protein synthesis with fMet in common with bacteria, this has been cited as evidence for the ].<ref>{{Cite book|last=Alberts,
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fMet is a starting residue in the synthesis of ] in bacteria, and, consequently, is located at the N-terminus of the growing ]. fMet is delivered to the ] (30S) - mRNA complex by a specialized ] (tRNA<sup>fMet</sup>) which has a 3'-UAC-5' ] that is capable of binding with the 5'-AUG-3'
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The ''N''-terminal fMet, if not removed by PDF, seems to act as a ], a signal for protein degradation.<ref name=p26866044>{{cite journal |last1=Piatkov |first1=KI |last2=Vu |first2=TT |last3=Hwang |first3=CS |last4=Varshavsky |first4=A |title=Formyl-methionine as a degradation signal at the
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Since fMet is present in proteins made by mitochondria and chloroplasts, more recent theories do not see it as a molecule that the immune system can use to distinguish self from non-self.<ref>{{cite journal | title = Circulating mitochondrial DAMPs cause inflammatory responses to injury |
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fMet plays a crucial part in the protein synthesis of bacteria, ] and ]s. It is not used in ]ic protein synthesis of ]s, where eukaryotic ]s are ]. It is also not used by ]. In the human body, fMet is recognized by the immune system as foreign material and stimulates the body to fight against
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The formyl group is not strictly required for initiation. Bacteria with their formyltransferase knocked out, which prevents Met-tRNA<sup>fMet</sup> (i.e. methionine loaded onto tRNA<sup>fMet</sup>) from turning into fMet-tRNA<sup>fMet</sup>, can have varying
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Because the fMet directs initiation, ]s in bacteria start (]) with a fMet residue instead of a methionine. Further occurrences of the "AUG" codon will result in a normal methionine, because a normal "elongating" tRNA<sup>Met</sup> is used.<ref
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fMet plays a crucial part in the protein synthesis of bacteria, ] and ]s. It is not used in ]ic protein synthesis of ]s, where eukaryotic ]s are ]. It is also not used by ]. In the human body, fMet is recognized by the immune system as foreign
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Bruce|url=https://www.worldcat.org/oclc/887605755|title=Molecular biology of the cell|date=18 November 2014|isbn=978-0-8153-4432-2|edition=Sixth|location=New York, NY|pages=800|oclc=887605755}}</ref>
92: 49: 927:| GHS_ref=<ref>{{cite web |title=N-Formyl-DL-methionine |url=https://pubchem.ncbi.nlm.nih.gov/compound/911#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> 11: 1688:=Detmers PA, Wright SD, Olsen E, Kimball B, Cohn ZA |title=Aggregation of complement receptors on human neutrophils in the absence of ligand |journal=] |volume=105 |issue=3 |pages=1137–45 | 1625:=Detmers PA, Wright SD, Olsen E, Kimball B, Cohn ZA |title=Aggregation of complement receptors on human neutrophils in the absence of ligand |journal=] |volume=105 |issue=3 |pages=1137–45 | 1519:
N-termini of bacterial proteins. |journal=Microbial Cell (Graz, Austria) |date=2015 |volume=2 |issue=10 |pages=376–393 |doi=10.15698/mic2015.10.231 |pmid=26866044 |pmc=4745127}}</ref>
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web|last=PubChem|title=N-Formyl-DL-methionine|url=https://pubchem.ncbi.nlm.nih.gov/compound/911|access-date=2020-10-24|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>
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The addition of the formyl group to methionine is catalyzed by the ] ]. This modification is done after methionine has been loaded onto tRNA<sup>fMet</sup> by ].
100: 116: 1478:=Sherman F, Stewart JW, Tsunasawa S |title=Methionine or not methionine at the beginning of a protein |journal=] |volume=3 |issue=1 |pages=27–31 | 1374:=Sherman F, Stewart JW, Tsunasawa S |title=Methionine or not methionine at the beginning of a protein |journal=] |volume=3 |issue=1 |pages=27–31 | 1298:
is catalyzed by the ] ]. This modification is done after methionine has been loaded onto tRNA<sup>fMet</sup> by ]. Methionine itself
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is a derivative of the ] ] in which a ] group has been added to the ] group. It is specifically used for initiation of ], and may be removed
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will catalyze the addition of the formyl group to methionine only if methionine has been loaded onto tRNA<sup>fMet</sup>
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will catalyze the addition of the formyl group to methionine only if methionine has been loaded onto tRNA<sup>fMet</sup>
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This is because the formyltransferase recognizes specific features of tRNA<sup>fMet</sup>.<ref name=p28204695/>
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is a derivative of the ] ] in which a ] group has been added to the ] group. It is specifically used for initiation of ]
240: 217: 1496:> MetAP only acts on proteins with second-position residues that are less bulky than valine.<ref name=p26866044/ 87: 1674:
https://web.archive.org/web/20100727061353/http://student.ccbcmd.edu/courses/bio141/lecguide/unit4/innate/prr.html
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methionine can be loaded either onto tRNA<sup>fMet</sup> or tRNA<sup>Met</sup>. However,
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a sequence of two enzymatic reactions. First, ] (PDF) deformylates it, converting the residue back to a normal
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can be loaded either onto tRNA<sup>fMet</sup> or tRNA<sup>Met</sup>. However,
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the attraction of circulating blood ] and then stimulate microbicidal activities such as
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use it to help distinguish self from non-self. ] can bind proteins starting with
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use it to help distinguish self from non-self. ] can bind proteins starting with
653:| StdInChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10) 1700:|url=http://www.jcb.org/cgi/pmidlookup?view=long&pmid=2958480}}</ref> 270: 247: 186: 266: 132: 408:| IUPACName = (''S'')-2-Formylamino-4-methylsulfanylbutanoic acid 112: 111: 261:
Alter: journal, pages. Add: pmc, bibcode, doi-access. Formatted
1621:=}}</ref><ref name="pmid2958480">{{cite journal | 1126:
and stimulates the body to fight against potential infection.
1684:}}</ref><ref name="pmid2958480">{{cite journal | 971:| PPhrases = {{P-phrases|264+265|280|305+351+338|337+317}} 456:| OtherNames = 2-Formylamino-4-methylsulfanyl-butyric acid 441:| OtherNames = 2-Formylamino-4-methylsulfanyl-butyric acid 1199:
Many organisms use variations of this basic mechanism.
139: 1124:, or as an alarm signal released by damaged cells, 432:(''S'')-2-Formylamino-4-methylsulfanylbutanoic acid 284:(67 intermediate revisions by 35 users not shown) 1486:1985 |pmid=3024631 |doi=10.1002/bies.950030108 | 1370:).<ref name="pmid3024631">{{cite journal | 1474:.<ref name="pmid3024631">{{cite journal | 1646:(other than in bacterially derived organelles) 1640:Because fMet is present in proteins made by 1597:Because fMet is present in proteins made by 664:| StdInChIKey = PYUSHNKNPOHWEZ-UHFFFAOYSA-N 377:| ImageFile = (S)-N-Formylmethionine V.1.svg 370:| ImageFile = (S)-N-Formylmethionine V.1.svg 214:Latest revision as of 10:24, 3 February 2024 1382:|pmid=3024631 |doi=10.1002/bies.950030108 | 307:{{DISPLAYTITLE:''N''-Formylmethionine}} 300:{{DISPLAYTITLE:''N''-Formylmethionine}} 1696:1987 |pmid=2958480 |pmc=2114803 |doi= 1443: 1350: 678: 634: 201:[[WP:CHEMVALID|Chem/Drugbox validation 158:Revision as of 21:07, 6 September 2011 1358:is removed from majority of proteins 77: 34: 1838:{{DEFAULTSORT:Formylmethionine, N-}} 1831:{{DEFAULTSORT:Formylmethionine, N-}} 1451:is removed from majority of proteins 1311:onto tRNA<sup>Met</sup>. 1283:onto tRNA<sup>Met</sup>. 1082:For-Met<ref name="iupacaa" />) 568:| UNII_Ref = {{fdacite|correct|FDA}} 528:| CASNo_Ref = {{cascite|correct|??}} 148: 131: 283: 259: 228: 211: 204: 198: 167: 155: 9: 1601:but not in those made by ], the ] 1472:removes the residue from the chain 1065:'''''N''-Formylmethionine''' (fMet 1019:'''''N''-Formylmethionine''' (fMet 120: 1978: 1154:==Function in protein synthesis== 1147:==Function in protein synthesis== 95: 81: 52: 38: 1294:addition of the formyl group to 493:|Section1={{Chembox Identifiers 361:| Name = ''N''-Formylmethionine 354:| Name = ''N''-Formylmethionine 1366:by methionine aminopeptidase ( 960:| HPhrases = {{H-phrases|319}} 743:| C=6 | H=11 | N=1 | O=3 | S=1 734:| C=6 | H=11 | N=1 | O=3 | S=1 725:|Section2={{Chembox Properties 1: 1961: 1950: 1939: 1928: 1917: 1908: 1897: 1888: 1845: 1770: 1759: 1748: 1737: 1728: 1716: 1707: 1636: 1593: 1555: 1546: 1535: 1526: 1514: 1505: 1425: 1416: 1404: 1395: 1333: 1286: 1265: 1242: 1232: 1208: 1194: 1185: 1159: 1117: 1109: 1061: 1015: 978: 967: 956: 945: 934: 923: 916:|Section7 = {{Chembox Hazards 912: 901: 888: 879: 836: 820: 739: 730: 721: 705: 660: 649: 618: 575: 564: 553: 542: 533: 524: 509: 498: 489: 473: 452: 437: 425: 411: 404: 392: 382: 338: 328: 273:. | Suggested by Abductive | 449:N-Formyl(methyl)homocysteine 14:Browse history interactively 7: 1588:==Relevance to immunology== 1581:==Relevance to immunology== 938:| GHSPictograms = {{GHS07}} 840:|Section3={{Chembox Hazards 468:-Formyl(methyl)homocysteine 1983: 1656:, and use them to initiate 1644:but not in those made by ] 1429:=== Further processing === 759:| MolarMass = 177.22 g/mol 752:| MolarMass = 177.22 g/mol 1968: 1957: 1946: 1935: 1924: 1906: 1902: 1886: 1843: 1810: 1807: 1768: 1757: 1746: 1735: 1726: 1714: 1705: 1553: 1544: 1533: 1524: 1512: 1503: 1455:both host and recombinant 1434: 1423: 1414: 1402: 1393: 1389: 1362:both host and recombinant 1331: 1249: 1230: 1206: 1202: 1183: 1167: 1164:start ] located on the ]. 976: 965: 954: 949:| GHSSignalWord = Warning 943: 932: 921: 910: 899: 895: 877: 783: 780: 669: 658: 647: 643: 616: 573: 562: 551: 522: 423: 291: 288: 210: 154: 153: 1698:10.1083/jcb.105.3.1137 417:''N''-Formylmethionine 1088:, and may be removed 486:{{Chembox Identifiers 277:| #UCB_Category 27/36 1114:potential infection. 718:{{Chembox Properties 595:| EINECS = 224-322-8 588:| EINECS = 224-322-8 109: 66: 1449:''N''-terminal fMet 1237:name=p28204695/> 1189:=== Translation === 1086:from ]l and ] genes 892:| Autoignition = }} 579:| UNII = PS9357B4XH 546:| CASNo = 4289-98-9 537:| CASNo = 4289-98-9 275:Category:Formamides 69: 26: 1607:N-Formylmethionine 1464:methionine. Then ] 1076:name="iupacaa"> 1067:,<ref>{{Cite 883:| AutoignitionPt = 622:| ChemSpiderID=887 342:| verifiedrevid = 332:| verifiedrevid = 226: 165: 74: 31: 1971: 1539:=== Variation === 1302:formyltransferase 833:{{Chembox Hazards 815:| Solubility = }} 808:| Solubility = }} 212: 156: 97: 83: 70: 54: 40: 27: 1974: 1631:|month=September 856:| MainHazards = 849:| MainHazards = 611:| PubChem = 911 604:| PubChem = 911 557:| ChEBI = 182822 460:Formylmethionine 445:Formylmethionine 430:|SystematicName= 278: 254: 244: 225: 220: 202: 193: 183: 164: 145: 144: 142: 137: 135: 127: 124: 113: 98: 84: 73: 55: 41: 30: 17: 15: 1982: 1981: 1977: 1976: 1975: 1973: 1972: 1966: 1955: 1944: 1933: 1922: 1913: 1900: 1893: 1882: 1875: 1866: 1859: 1850: 1839: 1832: 1823: 1818: 1803: 1796: 1787: 1782: 1775: 1764: 1753: 1742: 1731: 1722: 1710: 1701: 1699: 1695: 1691: 1687: 1683: 1679: 1675: 1671: 1667: 1663: 1659: 1655: 1651: 1647: 1643: 1634: 1632: 1628: 1624: 1620: 1616: 1612: 1608: 1604: 1600: 1589: 1582: 1573: 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1802:==References== 1801: 1799: 1797: 1795:==References== 1794: 1792: 1789: 1788: 1785: 1783: 1780: 1777: 1776: 1773: 1771: 1769: 1766: 1765: 1762: 1760: 1758: 1755: 1754: 1751: 1749: 1747: 1744: 1743: 1741:== See also == 1740: 1738: 1736: 1733: 1732: 1729: 1727: 1724: 1723: 1719: 1717: 1715: 1712: 1711: 1708: 1706: 1703: 1702: 1697: 1693: 1689: 1685: 1681: 1677: 1673: 1669: 1665: 1661: 1657: 1653: 1649: 1645: 1641: 1639: 1637: 1635: 1630: 1626: 1622: 1618: 1614: 1610: 1606: 1602: 1598: 1596: 1594: 1591: 1590: 1587: 1585: 1583: 1580: 1578: 1575: 1574: 1571: 1569: 1566: 1563: 1562: 1558: 1556: 1554: 1551: 1550: 1547: 1545: 1542: 1541: 1538: 1536: 1534: 1531: 1530: 1527: 1525: 1522: 1521: 1517: 1515: 1513: 1510: 1509: 1506: 1504: 1501: 1500: 1495: 1491: 1487: 1483: 1479: 1475: 1471: 1467: 1463: 1460: 1456: 1452: 1448: 1445: 1442: 1440: 1435: 1432: 1431: 1428: 1426: 1424: 1421: 1420: 1417: 1415: 1412: 1411: 1407: 1405: 1403: 1400: 1399: 1396: 1394: 1391: 1390: 1388: 1383: 1379: 1375: 1371: 1367: 1363: 1359: 1355: 1352: 1349: 1347: 1341: 1340: 1336: 1334: 1332: 1329: 1328: 1325: 1323: 1320: 1317: 1316: 1312: 1308: 1305: 1301: 1297: 1293: 1290: 1289: 1287: 1285: 1280: 1277:transformylase 1276: 1272: 1269: 1268: 1266: 1263: 1262: 1259: 1257: 1254: 1251: 1250: 1248: 1245: 1243: 1240: 1239: 1235: 1233: 1231: 1228: 1227: 1224: 1222: 1219: 1216: 1215: 1211: 1209: 1207: 1204: 1203: 1201: 1197: 1195: 1192: 1191: 1188: 1186: 1184: 1181: 1180: 1177: 1175: 1172: 1169: 1168: 1166: 1162: 1160: 1157: 1156: 1153: 1151: 1149: 1146: 1144: 1141: 1140: 1137: 1135: 1132: 1129: 1128: 1123: 1120: 1118: 1116: 1112: 1110: 1107: 1106: 1103: 1101: 1098: 1095: 1094: 1089: 1085: 1081: 1078: 1075: 1072: 1069: 1066: 1064: 1062: 1060: 1055: 1051: 1048: 1047: 1044: 1041: 1037: 1034: 1031: 1026: 1023: 1020: 1018: 1016: 1013: 1012: 1009: 1007: 1004: 1001: 1000: 997: 995: 993: 990: 988: 985: 984: 981: 979: 977: 974: 973: 970: 968: 966: 963: 962: 959: 957: 955: 952: 951: 948: 946: 944: 941: 940: 937: 935: 933: 930: 929: 926: 924: 922: 919: 918: 915: 913: 911: 908: 907: 904: 902: 900: 897: 896: 894: 891: 889: 886: 885: 882: 880: 878: 875: 874: 871: 869: 867: 864: 862: 859: 858: 855: 853: 851: 848: 846: 843: 842: 839: 837: 835: 831: 828: 825: 823: 821: 818: 817: 814: 812: 810: 807: 805: 802: 801: 799:| BoilingPt = 798: 796: 794: 792:| BoilingPt = 791: 789: 786: 785: 782: 778: 777: 774: 772: 770: 767: 765: 762: 761: 758: 756: 754: 751: 749: 746: 745: 742: 740: 738: 735: 733: 731: 728: 727: 724: 722: 720: 716: 713: 710: 708: 706: 703: 702: 699: 697: 695: 692: 690: 687: 686: 681: 677: 675: 670: 667: 666: 663: 661: 659: 656: 655: 652: 650: 648: 645: 644: 642: 637: 633: 631: 625: 624: 621: 619: 617: 614: 613: 610: 608: 606: 603: 601: 598: 597: 594: 592: 590: 587: 585: 582: 581: 578: 576: 574: 571: 570: 567: 565: 563: 560: 559: 556: 554: 552: 549: 548: 545: 543: 541: 538: 536: 534: 531: 530: 527: 525: 523: 520: 519: 514: 512: 510: 508: 503: 501: 499: 496: 495: 492: 490: 488: 484: 481: 478: 476: 474: 471: 470: 465: 461: 457: 455: 453: 451: 446: 442: 440: 438: 435: 434: 429: 428: 426: 424: 421: 420: 416: 415:| IUPACName = 414: 412: 410: 407: 405: 402: 401: 397: 396:| ImageSize = 395: 393: 391: 387: 386:| ImageSize = 385: 383: 380: 379: 376: 374: 372: 369: 367: 364: 363: 360: 358: 356: 353: 351: 348: 347: 343: 341: 339: 337: 333: 331: 329: 326: 325: 322: 320: 318: 315: 313: 310: 309: 306: 304: 302: 299: 297: 294: 293: 290: 286: 285: 281: 280: 251: 246: 245: 230: 209: 190: 185: 184: 169: 129: 121: 115: 99: 93: 85: 79: 76: 75: 68: 56: 50: 42: 36: 33: 32: 25: 23: 19: 18: 10: 6: 4: 3: 2: 1979: 1963: 1960: 1952: 1949: 1941: 1938: 1930: 1927: 1919: 1916: 1910: 1905: 1899: 1896: 1890: 1885: 1879: 1877: 1872: 1870: 1869: 1863: 1861: 1856: 1854: 1853: 1847: 1842: 1836: 1834: 1829: 1827: 1826: 1822: 1820: 1817: 1815: 1814: 1806: 1800: 1798: 1793: 1791: 1790: 1786: 1784: 1781: 1779: 1778: 1772: 1767: 1761: 1756: 1750: 1745: 1739: 1734: 1730: 1725: 1718: 1713: 1709: 1704: 1638: 1595: 1592: 1586: 1584: 1579: 1577: 1576: 1572: 1570: 1567: 1565: 1564: 1557: 1552: 1548: 1543: 1537: 1532: 1528: 1523: 1516: 1511: 1507: 1502: 1444: 1441: 1439: 1436: 1433: 1427: 1422: 1418: 1413: 1406: 1401: 1397: 1392: 1351: 1348: 1346: 1343: 1342: 1335: 1330: 1326: 1324: 1321: 1319: 1318: 1288: 1267: 1264: 1260: 1258: 1255: 1253: 1252: 1244: 1241: 1234: 1229: 1225: 1223: 1220: 1218: 1217: 1210: 1205: 1196: 1193: 1187: 1182: 1178: 1176: 1173: 1171: 1170: 1161: 1158: 1152: 1150: 1145: 1143: 1142: 1138: 1136: 1133: 1131: 1130: 1119: 1111: 1108: 1104: 1102: 1099: 1097: 1096: 1063: 1017: 1014: 1010: 1008: 1005: 1003: 1002: 996: 994: 989: 987: 986: 980: 975: 969: 964: 958: 953: 947: 942: 936: 931: 925: 920: 914: 909: 903: 898: 890: 887: 881: 876: 870: 868: 863: 861: 860: 854: 852: 847: 845: 844: 838: 822: 819: 813: 811: 806: 804: 803: 797: 795: 790: 788: 787: 779: 773: 771: 766: 764: 763: 757: 755: 750: 748: 747: 741: 732: 729: 723: 707: 704: 698: 696: 691: 689: 688: 679: 676: 674: 671: 668: 662: 657: 651: 646: 635: 632: 630: 627: 626: 620: 615: 609: 607: 602: 600: 599: 593: 591: 586: 584: 583: 577: 572: 566: 561: 555: 550: 544: 535: 532: 526: 521: 515:Abbreviations 511: 504:abbreviations 500: 497: 491: 475: 472: 454: 439: 436: 427: 422: 413: 406: 403: 394: 384: 381: 375: 373: 368: 366: 365: 359: 357: 352: 350: 349: 340: 330: 327: 321: 319: 314: 312: 311: 305: 303: 298: 296: 295: 287: 282: 276: 272: 268: 264: 249: 242: 238: 233: 224: 219: 215: 207: 188: 181: 177: 172: 163: 159: 143: 136: 126:Content added 118: 16: 1678:archive-date 1079:</ref> 872:| FlashPt = 865:| FlashPt = 684:(NC=O)C(O)=O 640:(NC=O)C(O)=O 267:Use this bot 231:Citation bot 1682:2010-07-27 1670:archive-url 1380:|month=July 680:| SMILES = 636:| SMILES = 271:Report bugs 1694:September 1662:url-status 1619:accessdate 1494:}}</ref 1356:methionine 1296:methionine 447:<br> 443:<br> 96:Revision 2 53:Revision 1 1492:33735710 344:448813033 334:431462664 323:{{chembox 316:{{chembox 253:5,218,860 1811:Line 87: 1808:Line 53: 1686:vauthors 1648:, the ] 1642:bacteria 1476:vauthors 1438:⚫ 1345:⚫ 1122:material 827:Section3 784:Line 30: 781:Line 22: 712:Section2 673:⚫ 629:⚫ 480:Section1 241:contribs 180:contribs 170:CheMoBot 141:Wikitext 1281:and NOT 1042:related 292:Line 1: 289:Line 1: 192:141,565 1623:author 1611:format 1372:author 263:dashes 134:Visual 82:Page 2 72:Page 2 39:Page 1 29:Page 1 1650:might 1629:=1987 1488:s2cid 1484:July 1468:MetAP 1378:=1985 1056:after 1035:found 638:CSCCC 517:=fMet 506:=fMet 398:200px 388:250px 255:edits 194:edits 1690:date 1666:dead 1654:fMet 1627:year 1615:work 1498:> 1480:date 1376:year 1353:This 1273:that 1270:Note 1040:and 1038:in ] 682:CSCC 462:; '' 265:. | 248:Bots 237:talk 223:undo 218:edit 187:Bots 176:talk 162:edit 1774:* ] 1763:* ] 1752:* ] 1617:= | 1613:= | 1603:can 1446:The 1384:url 1368:MAP 1309:not 1291:The 1459:by 1052:It 1049:]. 1024:is 998:}} 991:}} 982:}} 905:}} 700:}} 693:}} 513:| 502:| 466:'' 458:; 269:. 239:| 178:| 1965:] 1954:] 1943:] 1932:] 1921:] 1912:] 1892:] 1881:] 1874:] 1865:] 1858:] 1849:] 1692:= 1680:= 1676:| 1672:= 1668:| 1664:= 1599:] 1490:= 1482:= 1470:) 1466:( 1457:, 1453:, 1364:) 1360:( 1306:, 1092:. 1090:] 1058:. 1045:] 1032:] 1029:] 1027:a 1021:) 830:= 824:| 715:= 709:| 483:= 477:| 464:N 243:) 235:( 182:) 174:(

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