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N-Formylmethionine

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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
599:. Methionine itself can be loaded either onto tRNA or tRNA. However, formyltransferase will catalyze the addition of the formyl group to methionine only if methionine has been loaded onto tRNA, not onto tRNA. This is because the formyltransferase recognizes specific features of tRNA. 669:
The formyl group is not strictly required for initiation. Bacteria with their formyltransferase knocked out, which prevents Met-tRNA (i.e. methionine loaded onto tRNA) from turning into fMet-tRNA, can have varying degrees of residual ability to start protein synthesis.
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fMet is required for efficient initiaiton of protein synthesis in most groups of bacteria. The 30S ribosome–mRNA complex specifically recruits tRNAs with a formylated amino acid – tRNA attached to fMet in the natural case.
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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. Instead, fMet-containing
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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
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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.
557:. In the human body, fMet is recognized by the immune system as foreign material, or as an alarm signal released by damaged cells, and stimulates the body to fight against potential infection. 353: 742:
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
423: 630:, 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. 585:) 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 is used. 470: 1198: 961: 281: 879:"Two highly conserved features of bacterial initiator tRNAs license them to pass through distinct checkpoints in translation initiation" 650:(MetAP) removes the residue from the chain. MetAP only acts on proteins with second-position residues that are less bulky than valine. 747: 642:-terminal fMet is removed from majority of proteins, both host and recombinant, by a sequence of two enzymatic reactions. First, 465: 937: 1199:"The Innate Immune System: Pattern-Recognition Receptors, Antigen-Nonspecific Antimicrobial Body Molecules, and Cytokines" 131: 256: 592: 477: 1351: 523: 439: 1034:
Sherman F, Stewart JW, Tsunasawa S (July 1985). "Methionine or not methionine at the beginning of a protein".
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Zhang Q, Raoof M, Chen Y, Sumi Y, Sursal T, Junger W, Brohi K, Itagaki K, Hauser CJ (Mar 4, 2010).
769:). Acting through these receptors, the fMet-containing oligopeptides and proteins are part of the 726:
can bind proteins starting with fMet, and use them to initiate the attraction of circulating blood
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Because fMet is present in proteins made by bacteria but not in those made by
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Shetty, S; Shah, RA; Chembazhi, UV; Sah, S; Varshney, U (28 February 2017).
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InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)
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Nomenclature and Symbolism for Amino Acids and Peptides, 3AA-18 and 3AA-19
595:. This modification is done after methionine has been loaded onto tRNA by 894: 534: 1292: 1269:"Circulating mitochondrial DAMPs cause inflammatory responses to injury" 727: 715: 579: 499: 496: 338: 191: 170: 1216:
Detmers PA, Wright SD, Olsen E, Kimball B, Cohn ZA (September 1987).
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Except where otherwise noted, data are given for materials in their
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The addition of the formyl group to methionine is catalyzed by the
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fMet plays a crucial part in the protein synthesis of bacteria,
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of immunity. The prototypical fMet-containing oligopeptide is
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2-Formylamino-4-methylsulfanyl-butyric acid; Formylmethionine;
615: 507: 150: 120: 1191: 401: 1215: 657:-terminal fMet, if not removed by PDF, seems to act as a 1130: 1081: 1033: 977:"N-degron and C-degron pathways of protein degradation" 1131:
Piatkov, KI; Vu, TT; Hwang, CS; Varshavsky, A (2015).
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Piatkov, KI; Vu, TT; Hwang, CS; Varshavsky, A (2015).
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might use it to help distinguish self from non-self.
718:(other than in bacterially derived organelles), the 682:
show almost no remaining translation ability, while
730:and then stimulate microbicidal activities such as 1266: 510:group. It is specifically used for initiation of 1338: 560: 495:(fMet, HCO-Met, For-Met) is a derivative of the 221: 981:Proceedings of the National Academy of Sciences 106: 925: 932:(Sixth ed.). New York, NY. p. 800. 72:)-2-Formylamino-4-methylsulfanylbutanoic acid 1209: 1077: 1075: 872: 870: 868: 1027: 974: 960:: CS1 maint: location missing publisher ( 709: 610:cells, including those of humans, and the 178: 1329:at the U.S. National Library of Medicine 1300: 1243: 1158: 1148: 1107: 1010: 1000: 902: 856: 854: 241: 1072: 975:Varshavsky, Alexander (8 January 2019). 865: 14: 1339: 851: 751:-formylmethionine-leucyl-phenylalanine 698:still churn out plenty of protein. In 968: 633: 574:Because the fMet directs initiation, 268:Key: PYUSHNKNPOHWEZ-UHFFFAOYSA-N 158: 661:, a signal for protein degradation. 926:Alberts, Bruce (18 November 2014). 832: 212: 24: 773:; they function to initiate acute 25: 1378: 1320: 702:, this ability is facilitated by 593:methionyl-tRNA formyltransferase 455: 371: 322: 316: 36: 1260: 1175: 451:(at 25 °C , 100 kPa). 1137:Microbial Cell (Graz, Austria) 1124: 1088:Microbial Cell (Graz, Austria) 919: 826: 808: 565: 440:N-Formylmethionine (data page) 331: 325: 310: 13: 1: 929:Molecular biology of the cell 802: 704:bacterial initiation factor 2 561:Function in protein synthesis 664: 506:group has been added to the 7: 1223:The Journal of Cell Biology 780: 763:G protein coupled receptors 85:-Formyl(methyl)homocysteine 10: 1383: 553:. It is also not used by 522:genes, and may be removed 343:177.22 g/mol 797:Formyl peptide receptor 3 792:Formyl peptide receptor 2 787:Formyl peptide receptor 1 767:formyl peptide receptor 3 759:formyl peptide receptor 2 755:formyl peptide receptor 1 648:methionine aminopeptidase 597:aminoacyl-tRNA synthetase 445: 438: 433: 352: 347: 297: 277: 252: 90: 78: 62: 49: 44: 35: 1331:Medical Subject Headings 839:pubchem.ncbi.nlm.nih.gov 835:"N-Formyl-DL-methionine" 820:pubchem.ncbi.nlm.nih.gov 816:"N-Formyl-DL-methionine" 434:Supplementary data page 410:Precautionary statements 1150:10.15698/mic2015.10.231 1100:10.15698/mic2015.10.231 1002:10.1073/pnas.1816596116 724:Polymorphonuclear cells 710:Relevance to immunology 1352:Amino acid derivatives 1236:10.1083/jcb.105.3.1137 1050:10.1002/bies.950030108 883:Nucleic Acids Research 541:protein synthesis of 64:Systematic IUPAC name 771:innate immune system 620:endosymbiotic theory 537:. It is not used in 524:post-translationally 1293:10.1038/nature08780 1285:2010Natur.464..104Z 993:2019PNAS..116..358V 644:peptide deformylase 578:in bacteria start ( 545:, where eukaryotic 32: 1367:Dicarboxylic acids 1357:Sulfur amino acids 1327:N-Formylmethionine 895:10.1093/nar/gkw854 634:Further processing 478:Infobox references 31:-Formylmethionine 27: 1347:Alpha-Amino acids 1279:(7285): 104–107. 1182:Immunology at MCG 939:978-0-8153-4432-2 512:protein synthesis 493:-Formylmethionine 486:Chemical compound 484: 483: 396:Hazard statements 132:Interactive image 57:-Formylmethionine 16:(Redirected from 1374: 1315: 1314: 1304: 1264: 1258: 1257: 1247: 1213: 1207: 1206: 1201:. Archived from 1195: 1189: 1179: 1173: 1172: 1162: 1152: 1128: 1122: 1121: 1111: 1079: 1070: 1069: 1031: 1025: 1024: 1014: 1004: 972: 966: 965: 959: 951: 923: 917: 916: 906: 889:(4): 2040–2050. 874: 863: 858: 849: 848: 846: 845: 830: 824: 823: 812: 468: 462: 459: 458: 429: 425: 421: 417: 403: 375: 333: 327: 324: 318: 312: 305:Chemical formula 289:CSCC(NC=O)C(O)=O 245: 225: 214: 193: 182: 162: 134: 110: 40: 33: 26: 21: 1382: 1381: 1377: 1376: 1375: 1373: 1372: 1371: 1337: 1336: 1323: 1318: 1265: 1261: 1214: 1210: 1197: 1196: 1192: 1180: 1176: 1143:(10): 376–393. 1129: 1125: 1094:(10): 376–393. 1080: 1073: 1032: 1028: 973: 969: 953: 952: 940: 924: 920: 875: 866: 859: 852: 843: 841: 831: 827: 814: 813: 809: 805: 783: 712: 694:, and possibly 667: 636: 629: 568: 563: 487: 480: 475: 474: 473:  ?) 464: 460: 456: 452: 412: 398: 384: 368: 330: 321: 315: 307: 293: 290: 285: 284: 273: 270: 269: 266: 260: 259: 248: 228: 215: 203: 185: 165: 137: 124: 113: 100: 86: 74: 73: 58: 23: 22: 15: 12: 11: 5: 1380: 1370: 1369: 1364: 1359: 1354: 1349: 1335: 1334: 1322: 1321:External links 1319: 1317: 1316: 1259: 1230:(3): 1137–45. 1208: 1205:on 2010-07-27. 1190: 1174: 1123: 1071: 1026: 987:(2): 358–366. 967: 938: 918: 864: 850: 825: 806: 804: 801: 800: 799: 794: 789: 782: 779: 711: 708: 666: 663: 635: 632: 627: 567: 564: 562: 559: 485: 482: 481: 476: 454: 453: 449:standard state 446: 443: 442: 436: 435: 431: 430: 424:P305+P351+P338 413: 408: 405: 404: 399: 394: 391: 390: 385: 380: 377: 376: 369: 364: 361: 360: 350: 349: 345: 344: 341: 335: 334: 328: 319: 313: 308: 303: 300: 299: 295: 294: 292: 291: 288: 280: 279: 278: 275: 274: 272: 271: 267: 264: 263: 255: 254: 253: 250: 249: 247: 246: 238: 236: 230: 229: 227: 226: 218: 216: 208: 205: 204: 202: 201: 197: 195: 187: 186: 184: 183: 175: 173: 167: 166: 164: 163: 155: 153: 147: 146: 143: 142:Abbreviations 139: 138: 136: 135: 127: 125: 118: 115: 114: 112: 111: 103: 101: 96: 93: 92: 88: 87: 80: 76: 75: 67: 66: 60: 59: 53: 47: 46: 42: 41: 9: 6: 4: 3: 2: 1379: 1368: 1365: 1363: 1360: 1358: 1355: 1353: 1350: 1348: 1345: 1344: 1342: 1332: 1328: 1325: 1324: 1312: 1308: 1303: 1298: 1294: 1290: 1286: 1282: 1278: 1274: 1270: 1263: 1255: 1251: 1246: 1241: 1237: 1233: 1229: 1225: 1224: 1219: 1212: 1204: 1200: 1194: 1188: 1187: 1183: 1178: 1170: 1166: 1161: 1156: 1151: 1146: 1142: 1138: 1134: 1127: 1119: 1115: 1110: 1105: 1101: 1097: 1093: 1089: 1085: 1078: 1076: 1067: 1063: 1059: 1055: 1051: 1047: 1043: 1039: 1038: 1030: 1022: 1018: 1013: 1008: 1003: 998: 994: 990: 986: 982: 978: 971: 963: 957: 949: 945: 941: 935: 931: 930: 922: 914: 910: 905: 900: 896: 892: 888: 884: 880: 873: 871: 869: 862: 857: 855: 840: 836: 829: 821: 817: 811: 807: 798: 795: 793: 790: 788: 785: 784: 778: 776: 772: 768: 764: 760: 756: 752: 750: 745: 741: 740:oligopeptides 735: 733: 729: 725: 721: 720:immune system 717: 707: 705: 701: 700:P. aeruginosa 697: 693: 692:H. influenzae 689: 685: 684:P. aeruginosa 681: 677: 676:S. pneumoniae 673: 662: 660: 656: 651: 649: 645: 641: 631: 623: 621: 617: 613: 609: 605: 600: 598: 594: 591: 586: 584: 582: 577: 572: 558: 556: 552: 548: 547:nuclear genes 544: 540: 536: 532: 527: 525: 521: 517: 513: 509: 505: 501: 498: 494: 492: 479: 472: 467: 450: 444: 441: 437: 432: 414: 411: 407: 406: 400: 397: 393: 392: 389: 386: 383: 379: 378: 374: 370: 367: 363: 362: 358: 356: 351: 346: 342: 340: 337: 336: 309: 306: 302: 301: 296: 287: 286: 283: 276: 262: 261: 258: 251: 244: 240: 239: 237: 235: 232: 231: 224: 220: 219: 217: 211: 207: 206: 199: 198: 196: 194: 189: 188: 181: 177: 176: 174: 172: 169: 168: 161: 157: 156: 154: 152: 149: 148: 144: 141: 140: 133: 129: 128: 126: 122: 117: 116: 109: 105: 104: 102: 99: 95: 94: 89: 84: 77: 71: 65: 61: 56: 52: 48: 43: 39: 34: 30: 19: 1276: 1272: 1262: 1227: 1221: 1211: 1203:the original 1193: 1184: 1177: 1140: 1136: 1126: 1091: 1087: 1044:(1): 27–31. 1041: 1035: 1029: 984: 980: 970: 928: 921: 886: 882: 842:. Retrieved 838: 828: 819: 810: 775:inflammation 748: 744:Danger model 736: 732:phagocytosis 713: 699: 695: 691: 687: 683: 679: 675: 671: 668: 654: 652: 639: 637: 624: 612:chloroplasts 604:mitochondria 601: 587: 580: 573: 569: 535:chloroplasts 531:mitochondria 528: 490: 489: 488: 387: 354: 160:CHEBI:182822 91:Identifiers 82: 79:Other names 69: 54: 28: 757:(FPR1) and 696:S. faecalis 680:B. subtilis 566:Translation 502:in which a 382:Signal word 298:Properties 1362:Formamides 1341:Categories 1186:1/phagstep 844:2020-10-24 803:References 765:(see also 728:leukocytes 716:eukaryotes 608:eukaryotic 551:translated 543:eukaryotes 520:organellar 500:methionine 497:amino acid 366:Pictograms 339:Molar mass 243:PS9357B4XH 171:ChemSpider 119:3D model ( 98:CAS Number 51:IUPAC name 1037:BioEssays 956:cite book 948:887605755 833:PubChem. 688:S. aureus 665:Variation 626:fMet-tRNA 583:-terminus 539:cytosolic 516:bacterial 428:P337+P317 416:P264+P265 357:labelling 200:224-322-8 192:EC Number 108:4289-98-9 1311:20203610 1169:26866044 1118:26866044 1066:33735710 1021:30622213 913:28204695 781:See also 576:proteins 348:Hazards 1302:2843437 1281:Bibcode 1254:2958480 1245:2114803 1160:4745127 1109:4745127 1058:3024631 1012:6329975 989:Bibcode 904:5389676 761:(FPR2) 672:E. coli 555:Archaea 471:what is 469: ( 388:Warning 210:PubChem 1333:(MeSH) 1309:  1299:  1273:Nature 1252:  1242:  1167:  1157:  1116:  1106:  1064:  1056:  1019:  1009:  946:  936:  911:  901:  659:degron 590:enzyme 504:formyl 466:verify 463:  282:SMILES 45:Names 1062:S2CID 616:plant 514:from 508:amino 257:InChI 151:ChEBI 145:fMet 121:JSmol 1307:PMID 1250:PMID 1165:PMID 1114:PMID 1054:PMID 1017:PMID 962:link 944:OCLC 934:ISBN 909:PMID 678:and 653:The 638:The 602:The 549:are 533:and 518:and 420:P280 402:H319 234:UNII 18:FMet 1297:PMC 1289:doi 1277:464 1240:PMC 1232:doi 1228:105 1155:PMC 1145:doi 1104:PMC 1096:doi 1046:doi 1007:PMC 997:doi 985:116 899:PMC 891:doi 614:of 606:of 355:GHS 223:911 213:CID 180:887 1343:: 1305:. 1295:. 1287:. 1275:. 1271:. 1248:. 1238:. 1226:. 1220:. 1163:. 1153:. 1139:. 1135:. 1112:. 1102:. 1090:. 1086:. 1074:^ 1060:. 1052:. 1040:. 1015:. 1005:. 995:. 983:. 979:. 958:}} 954:{{ 942:. 907:. 897:. 887:45 885:. 881:. 867:^ 853:^ 837:. 818:. 734:. 686:, 674:, 622:. 526:. 426:, 422:, 418:, 359:: 320:11 1313:. 1291:: 1283:: 1256:. 1234:: 1171:. 1147:: 1141:2 1120:. 1098:: 1092:2 1068:. 1048:: 1042:3 1023:. 999:: 991:: 964:) 950:. 915:. 893:: 847:. 822:. 749:N 690:, 655:N 640:N 628:i 581:N 491:N 461:Y 332:S 329:3 326:O 323:N 317:H 314:6 311:C 123:) 83:N 70:S 68:( 55:N 29:N 20:)

Index

FMet

IUPAC name
Systematic IUPAC name
CAS Number
4289-98-9
JSmol
Interactive image
ChEBI
CHEBI:182822
ChemSpider
887
EC Number
PubChem
911
UNII
PS9357B4XH
InChI
SMILES
Chemical formula
Molar mass
GHS labelling
Pictograms
GHS07: Exclamation mark
Signal word
Hazard statements
Precautionary statements
N-Formylmethionine (data page)
standard state
verify

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