256:
181:
37:
1195:
1205:
383:
118:
528:. A pentapeptide composed of L-alanyl-D-isoglutaminyl-L-lysyl-D-alanyl-D-alanine is added to the MurNAc in the process of making the peptidoglycan strands of the cell wall.
396:
279:
InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
289:
InChI=1/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
305:
391:
569:
542:
to inhibit pathogens from growing within the body. Therefore, both NAG and NAM are valuable polymers in medicinal research.
1134:
520:-Acetylmuramic acid (MurNAc) is part of the peptidoglycan polymer of bacterial cell walls. MurNAc is covalently linked to
1234:
901:
641:
270:
403:
891:
818:
1015:
746:
62:
213:
176:
234:
856:
1244:
1208:
251:
1239:
1010:
933:
896:
692:
524:-acetylglucosamine and may also be linked through the hydroxyl on carbon number 4 to the carbon of
20:
1086:
1005:
984:
634:
1229:
1126:
768:
158:
49:
841:
824:
662:
222:
94:
8:
1091:
976:
971:
864:
834:
687:
672:
498:
471:
84:
255:
180:
138:
1121:
1020:
829:
741:
734:
1198:
1061:
1027:
994:
851:
846:
804:
751:
627:
588:
202:
913:
789:
724:
578:
328:
1139:
1038:
923:
799:
729:
682:
565:
activity of fosfomycin in combination with various antistaphylococcal substances"
794:
758:
374:
1223:
1148:
1033:
989:
961:
952:
942:
918:
814:
460:
169:
1178:
1163:
1043:
784:
702:
650:
592:
583:
560:
482:
1066:
619:
614:
609:
486:
1173:
1158:
1076:
809:
539:
532:
359:
149:
36:
1168:
999:
957:
869:
763:
525:
506:
467:
373:
Except where otherwise noted, data are given for materials in their
677:
654:
464:
559:
Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F (2001).
505:-acetylglucosamine. This addition happens exclusively in the cell
117:
1107:
1071:
707:
189:
1153:
908:
1081:
129:
107:
239:
558:
429:) is an organic compound with the chemical formula
1221:
201:
93:
538:NAG and NAM cross-linking can be inhibited by
635:
552:
470:, which is built from alternating units of
649:
642:
628:
254:
179:
157:
582:
221:
512:
250:
1222:
170:
623:
570:Journal of Antimicrobial Chemotherapy
481:-acetylmuramic acid, cross-linked by
282:Key: MNLRQHMNZILYPY-MKFCKLDKSA-N
137:
1204:
492:
292:Key: MNLRQHMNZILYPY-MKFCKLDKBR
192:
13:
14:
1256:
531:Synthesis of NAM is inhibited by
1203:
1194:
1193:
381:
346:
340:
35:
892:Bacterial cellular morphologies
377:(at 25 °C , 100 kPa).
313:O=C(O)(O1(O)(OC(O)1NC(=O)C)CO)C
497:NAM is an addition product of
349:
334:
1:
545:
7:
603:
10:
1261:
1235:Monosaccharide derivatives
1135:Bacteria (classifications)
857:Primary nutritional groups
18:
1189:
1120:
1100:
1052:
941:
932:
884:
777:
715:
701:
661:
371:
321:
301:
266:
77:
61:
48:
43:
34:
1011:Bacterial outer membrane
19:Not to be confused with
71:)-2-{oxy}propanoic acid
21:N-Acetylneuraminic acid
1006:Gram-negative bacteria
985:Gram-positive bacteria
861:Substrate preference
513:Clinical significance
459:. It is a monomer of
63:Systematic IUPAC name
842:Microbial metabolism
584:10.1093/jac/48.2.209
489:residue of MurNAc.
30:-Acetylmuramic acid
1092:Non-motile bacteria
688:Pathogenic bacteria
499:phosphoenolpyruvate
419:-Acetylmuramic acid
367: g·mol
56:-Acetylmuramic acid
31:
1021:Lipopolysaccharide
475:-acetylglucosamine
404:Infobox references
26:
1217:
1216:
1116:
1115:
1062:Bacterial capsule
1028:Periplasmic space
995:Lipoteichoic acid
880:
879:
852:Microbial ecology
847:Nitrogen fixation
412:Chemical compound
410:
409:
235:CompTox Dashboard
119:Interactive image
16:Chemical compound
1252:
1245:Membrane biology
1207:
1206:
1197:
1196:
1145:Former groupings
939:
938:
790:Human microbiome
713:
712:
644:
637:
630:
621:
620:
597:
596:
586:
556:
493:Formation of NAM
458:
457:
456:
448:
447:
439:
438:
394:
388:
385:
384:
366:
351:
348:
342:
336:
329:Chemical formula
259:
258:
243:
241:
225:
205:
194:
183:
172:
161:
141:
121:
97:
39:
32:
25:
1260:
1259:
1255:
1254:
1253:
1251:
1250:
1249:
1240:Monosaccharides
1220:
1219:
1218:
1213:
1185:
1140:Bacterial phyla
1124:
1112:
1096:
1054:
1048:
1039:Arabinogalactan
944:
928:
876:
773:
717:
705:
697:
683:Lysogenic cycle
664:
657:
648:
606:
601:
600:
557:
553:
548:
515:
495:
455:
452:
451:
450:
446:
443:
442:
441:
437:
434:
433:
432:
430:
413:
406:
401:
400:
399: ?)
390:
386:
382:
378:
364:
354:
345:
339:
331:
317:
314:
309:
308:
297:
294:
293:
290:
284:
283:
280:
274:
273:
262:
244:
237:
228:
208:
195:
164:
144:
124:
111:
100:
87:
73:
72:
57:
24:
17:
12:
11:
5:
1258:
1248:
1247:
1242:
1237:
1232:
1215:
1214:
1212:
1211:
1201:
1190:
1187:
1186:
1184:
1183:
1182:
1181:
1176:
1171:
1166:
1156:
1151:
1142:
1137:
1131:
1129:
1118:
1117:
1114:
1113:
1111:
1110:
1104:
1102:
1098:
1097:
1095:
1094:
1089:
1084:
1079:
1074:
1069:
1064:
1058:
1056:
1050:
1049:
1047:
1046:
1041:
1030:
1025:
1024:
1023:
1018:
1002:
997:
992:
981:
980:
979:
974:
969:
955:
949:
947:
936:
930:
929:
927:
926:
921:
916:
911:
906:
905:
904:
899:
897:cell structure
888:
886:
882:
881:
878:
877:
875:
874:
873:
872:
870:Saccharophilic
867:
859:
854:
849:
844:
839:
838:
837:
832:
827:
822:
812:
807:
802:
797:
787:
781:
779:
775:
774:
772:
771:
766:
761:
759:Microaerophile
756:
755:
754:
749:
739:
738:
737:
732:
721:
719:
710:
699:
698:
696:
695:
690:
685:
680:
675:
669:
667:
659:
658:
647:
646:
639:
632:
624:
618:
617:
612:
605:
602:
599:
598:
577:(2): 209–217.
550:
549:
547:
544:
514:
511:
494:
491:
453:
444:
435:
411:
408:
407:
402:
380:
379:
375:standard state
372:
369:
368:
362:
356:
355:
352:
343:
337:
332:
327:
324:
323:
319:
318:
316:
315:
312:
304:
303:
302:
299:
298:
296:
295:
291:
288:
287:
285:
281:
278:
277:
269:
268:
267:
264:
263:
261:
260:
252:DTXSID70893663
247:
245:
233:
230:
229:
227:
226:
218:
216:
210:
209:
207:
206:
198:
196:
188:
185:
184:
174:
166:
165:
163:
162:
154:
152:
146:
145:
143:
142:
134:
132:
126:
125:
123:
122:
114:
112:
105:
102:
101:
99:
98:
90:
88:
83:
80:
79:
75:
74:
66:
65:
59:
58:
52:
46:
45:
41:
40:
15:
9:
6:
4:
3:
2:
1257:
1246:
1243:
1241:
1238:
1236:
1233:
1231:
1228:
1227:
1225:
1210:
1202:
1200:
1192:
1191:
1188:
1180:
1177:
1175:
1172:
1170:
1167:
1165:
1162:
1161:
1160:
1157:
1155:
1152:
1150:
1149:Schizomycetes
1146:
1143:
1141:
1138:
1136:
1133:
1132:
1130:
1128:
1123:
1119:
1109:
1106:
1105:
1103:
1099:
1093:
1090:
1088:
1085:
1083:
1080:
1078:
1075:
1073:
1070:
1068:
1065:
1063:
1060:
1059:
1057:
1051:
1045:
1042:
1040:
1037:
1035:
1031:
1029:
1026:
1022:
1019:
1017:
1014:
1013:
1012:
1009:
1007:
1003:
1001:
998:
996:
993:
991:
990:Teichoic acid
988:
986:
982:
978:
975:
973:
970:
968:
965:
964:
963:
962:Peptidoglycan
959:
956:
954:
953:Cell membrane
951:
950:
948:
946:
940:
937:
935:
931:
925:
922:
920:
917:
915:
912:
910:
907:
903:
900:
898:
895:
894:
893:
890:
889:
887:
883:
871:
868:
866:
863:
862:
860:
858:
855:
853:
850:
848:
845:
843:
840:
836:
833:
831:
828:
826:
823:
820:
816:
813:
811:
808:
806:
803:
801:
798:
796:
793:
792:
791:
788:
786:
783:
782:
780:
776:
770:
767:
765:
762:
760:
757:
753:
750:
748:
745:
744:
743:
740:
736:
733:
731:
728:
727:
726:
723:
722:
720:
714:
711:
709:
704:
700:
694:
691:
689:
686:
684:
681:
679:
676:
674:
671:
670:
668:
666:
660:
656:
652:
645:
640:
638:
633:
631:
626:
625:
622:
616:
613:
611:
608:
607:
594:
590:
585:
580:
576:
572:
571:
566:
564:
555:
551:
543:
541:
536:
534:
529:
527:
523:
519:
510:
508:
504:
500:
490:
488:
484:
483:oligopeptides
480:
477:(GlcNAc) and
476:
474:
469:
466:
462:
461:peptidoglycan
428:
424:
420:
418:
405:
398:
393:
376:
370:
363:
361:
358:
357:
333:
330:
326:
325:
320:
311:
310:
307:
300:
286:
276:
275:
272:
265:
257:
253:
249:
248:
246:
236:
232:
231:
224:
220:
219:
217:
215:
212:
211:
204:
200:
199:
197:
191:
187:
186:
182:
178:
175:
173:
171:ECHA InfoCard
168:
167:
160:
156:
155:
153:
151:
148:
147:
140:
136:
135:
133:
131:
128:
127:
120:
116:
115:
113:
109:
104:
103:
96:
92:
91:
89:
86:
82:
81:
76:
70:
64:
60:
55:
51:
47:
42:
38:
33:
29:
22:
1230:Amino sugars
1179:Mendosicutes
1164:Gracilicutes
1144:
1044:Mycolic acid
1034:Mycobacteria
1032:
1004:
983:
966:
919:Coccobacilli
819:in pregnancy
785:Extremophile
769:Aerotolerant
703:Biochemistry
665:microbiology
651:Microbiology
574:
568:
562:
554:
537:
530:
521:
517:
516:
502:
496:
478:
472:
426:
422:
416:
415:
414:
78:Identifiers
68:
53:
27:
1067:Slime layer
747:Facultative
735:Facultative
615:Glucosamine
610:Amino sugar
540:antibiotics
487:lactic acid
322:Properties
177:100.031.092
139:CHEBI:21615
1224:Categories
1174:Mollicutes
1169:Firmicutes
1159:Prokaryota
1077:Glycocalyx
902:plasticity
865:Lipophilic
718:preference
693:Resistance
546:References
533:fosfomycin
468:cell walls
360:Molar mass
223:246FXU111L
150:ChemSpider
106:3D model (
95:10597-89-4
85:CAS Number
50:IUPAC name
1127:evolution
1101:Composite
1000:Endospore
958:Cell wall
934:Structure
825:Placental
764:Nanaerobe
742:Anaerobic
673:Infection
526:L-alanine
507:cytoplasm
465:bacterial
1199:Category
1122:Taxonomy
1055:envelope
945:envelope
835:Salivary
752:Obligate
730:Obligate
678:Exotoxin
655:Bacteria
604:See also
593:11481290
563:In vitro
463:in most
1209:Commons
1108:Biofilm
1087:Fimbria
1072:S-layer
1053:Outside
914:Bacilli
830:Uterine
815:Vaginal
725:Aerobic
708:ecology
663:Medical
485:at the
397:what is
395: (
365:293.272
203:5462244
190:PubChem
159:4575341
1154:Monera
924:Spiral
716:Oxygen
591:
427:MurNAc
392:verify
389:
306:SMILES
44:Names
1082:Pilus
1036:only:
1016:Porin
1008:only:
987:only:
909:Cocci
885:Shape
805:Mouth
778:Other
271:InChI
130:ChEBI
108:JSmol
1125:and
943:Cell
810:Skin
800:Lung
706:and
589:PMID
501:and
214:UNII
977:DAP
972:NAG
967:NAM
795:Gut
579:doi
509:.
425:or
423:NAM
240:EPA
193:CID
1226::
1147::
960::
653::
587:.
575:48
573:.
567:.
535:.
449:NO
445:19
436:11
344:19
338:11
67:(2
821:)
817:(
643:e
636:t
629:v
595:.
581::
561:"
522:N
518:N
503:N
479:N
473:N
454:8
440:H
431:C
421:(
417:N
387:N
353:8
350:O
347:N
341:H
335:C
242:)
238:(
110:)
69:R
54:N
28:N
23:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
