375:
220:
24:
586:
830:
Alvarez-Carreno, Claudia; Becerra, Arturo; Lazcano, Antonio "Norvaline and
Norleucine May Have Been More Abundant Protein Components during Early Stages of Cell Evolution" Origins of Life and Evolution of Biospheres 2014, volume 43, 363-375.
909:
864:
Clementi, ME & Misiti, F (Nov 2005). "Substitution of methionine 35 inhibits apoptotic effects of Abeta(31-35) and Abeta(25-35) fragments of amyloid-beta protein in PC12 cells".
797:
The use of the name norleucine is discouraged as it is a misnomer, given than nor is defined for an amino acid with one less methylene group than found in the proteinogenic form.
599:
414:
902:
847:
Moroder, Luis "Isosteric replacement of sulfur with other chalcogens in peptides and proteins" Journal of
Peptide Science 2005, volume 11, 187-214.
1365:
1309:
895:
760:
389:
649:
H. A systematic name for this compound is 2-aminohexanoic acid. The compound is an isomer of the more common amino acid
1299:
918:
332:
673:, norleucine is found in small amounts in some bacterial strains where its concentration can approach millimolar. Its
1022:
353:
690:
1360:
678:
606:
503:
1211:
686:
227:
945:
277:
1017:
981:
215:
107:
1319:
1163:
1085:
714:
283:
1314:
1304:
1227:
721:
at the 35 position with norleucine the neurotoxic effects of the Aβ peptides were completely negated.
1324:
1113:
36:
370:
1273:
1139:
1133:
963:
68:
137:
125:
1339:
1247:
1007:
973:
873:
685:. The incorporation of Nle into peptides reflects the imperfect selectivity of the associated
682:
539:
1105:
848:
832:
811:
693:
probing prebiotic synthesis of amino acids, norleucine and especially norvaline are formed.
492:
437:
177:
341:
1027:
987:
374:
246:
219:
654:
78:
157:
1185:
1091:
935:
577:
1354:
1334:
1151:
481:
208:
1244:
1179:
1050:
710:
674:
567:
1063:
1058:
305:
1293:
953:
887:
709:. For this reason, norleucine has been used to probe the role of methionine in
1329:
1260:
1077:
1012:
836:
718:
702:
626:
549:
468:
168:
1255:
1174:
1169:
927:
816:
799:
736:
670:
534:
528:
877:
1191:
1145:
730:
188:
197:
23:
1279:
1037:
650:
544:
292:
228:
1041:
999:
740:
706:
658:
554:
852:
576:
Except where otherwise noted, data are given for materials in their
266:
316:
148:
106:
96:
257:
891:
398:
InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
358:
800:"Nomenclature and Symbolism For Amino Acids and Peptides"
594:
743:
that has similar biochemistry to that of norleucine.
486:301 °C (574 °F; 574 K) (decomposes)
1243:
1236:
1220:
1204:
1126:
1104:
1076:
1049:
1036:
997:
972:
944:
925:
717:. A study showed that with the substitution of the
713:(AβP) the central constituent of senile plaques in
788:, 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.
124:
784:Hermann Römpp, Jürgen Falbe und Manfred Regitz:
304:
677:has been examined. It arises via the action of
77:
903:
8:
1240:
1123:
1101:
1073:
1046:
910:
896:
888:
373:
218:
176:
15:
815:
340:
753:
733:, description of the isomers of leucine
419:
394:
369:
282:
196:
661:. It is a white, water-soluble solid.
209:
401:Key: LRQKBLKVPFOOQJ-UHFFFAOYSA-N
156:
7:
295:
265:
705:, even though it does not contain
14:
775:, Oxford, Clarendon Press, 1959.
584:
455:
449:
22:
580:(at 25 °C , 100 kPa).
516:2.39 (carboxyl), 9.76 (amino)
458:
443:
1:
1366:Non-proteinogenic amino acids
919:Non-proteinogenic amino acids
773:Data for Biochemical Research
761:Sicherheitsdatenblatt Acros.
701:It is nearly isosteric with
552:(2-amino-3-methyl-pentanoic)
547:(2-amino-4-methyl-pentanoic)
1212:List of abiotic amino acids
1023:Azetidine-2-carboxylic acid
1382:
804:Pure and Applied Chemistry
679:2-isopropylmalate synthase
1288:
837:10.1007/s11084-013-9344-3
687:aminoacyl-tRNA synthetase
574:
520:
430:
410:
385:
61:
51:
35:
30:
21:
771:Dawson, R.M.C., et al.,
982:gamma-Aminobutyric acid
817:10.1351/pac198456050595
691:Miller–Urey experiments
557:(2,6-diamino-hexanoic)
1221:Engineered amino acids
1164:Dihydroxyphenylglycine
1086:2-Aminoisobutyric acid
45:)-2-Aminohexanoic acid
1228:Expanded genetic code
1114:Carboxyglutamic acid
810:(5): 595–624. 1984.
786:Römpp Lexikon Chemie
37:Preferred IUPAC name
1274:Aminolevulinic acid
1205:Abiotic amino acids
1140:Aminolevulinic acid
1134:4-Aminobenzoic acid
964:Diaminopimelic acid
946:bacterial cell wall
715:Alzheimer's disease
629:with the formula CH
537:(2-amino-pentanoic)
493:Solubility in water
476: g·mol
138:Beilstein Reference
18:
1340:Dehydroamino acids
1300:Encoded (proteins)
653:. Like most other
607:Infobox references
542:(6-amino-hexanoic)
521:Related compounds
16:
1361:Alpha-Amino acids
1348:
1347:
1310:Non-proteinogenic
1269:
1268:
1248:citric acid cycle
1200:
1199:
1122:
1121:
1100:
1099:
1072:
1071:
1008:ADDA (amino acid)
974:neurotransmitters
711:Amyloid-β peptide
615:Chemical compound
613:
612:
563:Related compounds
540:Aminocaproic acid
498:16 g/L at 23 °C
354:CompTox Dashboard
108:Interactive image
1373:
1241:
1124:
1106:clotting factors
1102:
1074:
1047:
912:
905:
898:
889:
882:
881:
861:
855:
845:
839:
828:
822:
821:
819:
795:
789:
782:
776:
769:
763:
758:
657:, norleucine is
621:(abbreviated as
597:
591:
588:
587:
475:
460:
457:
451:
445:
438:Chemical formula
378:
377:
362:
360:
344:
308:
297:
286:
269:
247:Gmelin Reference
230:
222:
211:
200:
180:
160:
128:
110:
81:
26:
19:
1381:
1380:
1376:
1375:
1374:
1372:
1371:
1370:
1351:
1350:
1349:
1344:
1343:
1325:Secondary amino
1284:
1265:
1232:
1216:
1196:
1118:
1096:
1068:
1032:
1028:Quisqualic acid
993:
988:Quisqualic acid
968:
940:
921:
916:
886:
885:
872:(11): BR381-5.
866:Med. Sci. Monit
863:
862:
858:
853:10.1002/psc.654
846:
842:
829:
825:
798:
796:
792:
783:
779:
770:
766:
759:
755:
750:
727:
699:
667:
648:
644:
640:
636:
632:
616:
609:
604:
603:
602: ?)
593:
589:
585:
581:
564:
553:
548:
543:
538:
531:
512:
495:
473:
463:
454:
448:
440:
426:
423:
418:
417:
406:
403:
402:
399:
393:
392:
381:
363:
356:
347:
327:
311:
298:
272:
249:
240:
203:
183:
163:
140:
131:
113:
100:
89:
71:
57:
55:
47:
46:
12:
11:
5:
1379:
1377:
1369:
1368:
1363:
1353:
1352:
1346:
1345:
1342:
1337:
1332:
1327:
1322:
1317:
1312:
1307:
1302:
1290:
1289:
1286:
1285:
1283:
1282:
1277:
1270:
1267:
1266:
1264:
1263:
1258:
1252:
1250:
1238:
1234:
1233:
1231:
1230:
1224:
1222:
1218:
1217:
1215:
1214:
1208:
1206:
1202:
1201:
1198:
1197:
1195:
1194:
1189:
1186:Hydroxyproline
1183:
1177:
1172:
1167:
1161:
1155:
1149:
1143:
1137:
1130:
1128:
1120:
1119:
1117:
1116:
1110:
1108:
1098:
1097:
1095:
1094:
1092:Enduracididine
1089:
1082:
1080:
1070:
1069:
1067:
1066:
1061:
1055:
1053:
1044:
1034:
1033:
1031:
1030:
1025:
1020:
1015:
1010:
1004:
1002:
995:
994:
992:
991:
985:
978:
976:
970:
969:
967:
966:
961:
956:
950:
948:
942:
941:
939:
938:
936:Hydroxyproline
932:
930:
923:
922:
917:
915:
914:
907:
900:
892:
884:
883:
856:
840:
823:
790:
777:
764:
752:
751:
749:
746:
745:
744:
734:
726:
723:
698:
695:
683:α-ketobutyrate
669:Together with
666:
663:
646:
642:
638:
634:
630:
614:
611:
610:
605:
583:
582:
578:standard state
575:
572:
571:
565:
562:
559:
558:
532:
526:
523:
522:
518:
517:
514:
510:
500:
499:
496:
491:
488:
487:
484:
478:
477:
471:
465:
464:
461:
452:
446:
441:
436:
433:
432:
428:
427:
425:
424:
422:CCCCC(N)C(O)=O
421:
413:
412:
411:
408:
407:
405:
404:
400:
397:
396:
388:
387:
386:
383:
382:
380:
379:
371:DTXSID40861874
366:
364:
352:
349:
348:
346:
345:
337:
335:
329:
328:
326:
325:
321:
319:
313:
312:
310:
309:
301:
299:
291:
288:
287:
280:
274:
273:
271:
270:
262:
260:
254:
253:
250:
245:
242:
241:
239:
238:
234:
232:
224:
223:
213:
205:
204:
202:
201:
193:
191:
185:
184:
182:
181:
173:
171:
165:
164:
162:
161:
153:
151:
145:
144:
141:
136:
133:
132:
130:
129:
121:
119:
115:
114:
112:
111:
103:
101:
94:
91:
90:
88:
87:
74:
72:
67:
64:
63:
59:
58:
53:
49:
48:
40:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1378:
1367:
1364:
1362:
1359:
1358:
1356:
1341:
1338:
1336:
1335:D-amino acids
1333:
1331:
1328:
1326:
1323:
1321:
1318:
1316:
1313:
1311:
1308:
1306:
1303:
1301:
1297:
1295:
1291:
1287:
1281:
1278:
1275:
1272:
1271:
1262:
1259:
1257:
1254:
1253:
1251:
1249:
1246:
1242:
1239:
1237:Intermediates
1235:
1229:
1226:
1225:
1223:
1219:
1213:
1210:
1209:
1207:
1203:
1193:
1190:
1187:
1184:
1181:
1178:
1176:
1173:
1171:
1168:
1165:
1162:
1159:
1156:
1153:
1152:Penicillamine
1150:
1148:(insectiside)
1147:
1144:
1141:
1138:
1135:
1132:
1131:
1129:
1125:
1115:
1112:
1111:
1109:
1107:
1103:
1093:
1090:
1087:
1084:
1083:
1081:
1079:
1075:
1065:
1062:
1060:
1057:
1056:
1054:
1052:
1051:Beta-peptides
1048:
1045:
1043:
1039:
1035:
1029:
1026:
1024:
1021:
1019:
1016:
1014:
1011:
1009:
1006:
1005:
1003:
1001:
996:
989:
986:
983:
980:
979:
977:
975:
971:
965:
962:
960:
957:
955:
952:
951:
949:
947:
943:
937:
934:
933:
931:
929:
924:
920:
913:
908:
906:
901:
899:
894:
893:
890:
879:
875:
871:
867:
860:
857:
854:
850:
844:
841:
838:
834:
827:
824:
818:
813:
809:
805:
801:
794:
791:
787:
781:
778:
774:
768:
765:
762:
757:
754:
747:
742:
738:
735:
732:
729:
728:
724:
722:
720:
716:
712:
708:
704:
696:
694:
692:
688:
684:
680:
676:
672:
664:
662:
660:
656:
655:α-amino acids
652:
628:
624:
620:
608:
601:
596:
579:
573:
569:
566:
561:
560:
556:
551:
546:
541:
536:
533:
530:
525:
524:
519:
515:
509:
505:
502:
501:
497:
494:
490:
489:
485:
483:
482:Melting point
480:
479:
472:
470:
467:
466:
442:
439:
435:
434:
429:
420:
416:
409:
395:
391:
384:
376:
372:
368:
367:
365:
355:
351:
350:
343:
339:
338:
336:
334:
331:
330:
323:
322:
320:
318:
315:
314:
307:
303:
302:
300:
294:
290:
289:
285:
281:
279:
276:
275:
268:
264:
263:
261:
259:
256:
255:
251:
248:
244:
243:
236:
235:
233:
231:
226:
225:
221:
217:
214:
212:
210:ECHA InfoCard
207:
206:
199:
195:
194:
192:
190:
187:
186:
179:
175:
174:
172:
170:
167:
166:
159:
155:
154:
152:
150:
147:
146:
142:
139:
135:
134:
127:
123:
122:
120:
117:
116:
109:
105:
104:
102:
98:
93:
92:
85:
80:
76:
75:
73:
70:
66:
65:
60:
50:
44:
38:
34:
29:
25:
20:
1292:
1245:Mitochondria
1180:Homocysteine
1160:(Alzheimers)
1157:
1142:(metabolism)
958:
869:
865:
859:
843:
826:
807:
803:
793:
785:
780:
772:
767:
756:
739:, isomer of
700:
675:biosynthesis
668:
622:
618:
617:
568:Caproic acid
507:
317:RTECS number
83:
62:Identifiers
56:Glycoleucine
52:Other names
42:
1330:Imino acids
1294:Amino acids
1154:(chelation)
954:Lanthionine
570:(hexanoic)
431:Properties
216:100.009.512
158:CHEBI:36405
17:Norleucine
1355:Categories
1320:Glucogenic
1261:Citrulline
1188:(collagen)
1158:Norleucine
1078:Antibiotic
1018:thialysine
1013:Canavanine
959:Norleucine
748:References
719:methionine
703:methionine
665:Occurrence
627:amino acid
619:Norleucine
550:Isoleucine
529:Aminoacids
469:Molar mass
342:832C8OV84S
284:Norleucine
169:ChemSpider
95:3D model (
69:CAS Number
1315:Ketogenic
1305:Essential
1256:Ornithine
1175:Norvaline
1170:Sarcosine
1064:β-Leucine
1059:β-Alanine
928:cell wall
737:norvaline
671:norvaline
535:Norvaline
324:RC6308000
237:210-462-7
229:EC Number
1192:Hypusine
1146:Canaline
878:16258386
731:Leucines
725:See also
625:) is an
527:Related
189:DrugBank
143:1721748
82: (2
79:327-57-1
1280:Cystine
1276:(5-ALA)
1182:(heart)
1038:Medical
990:(toxic)
651:leucine
600:what is
598: (
545:Leucine
504:Acidity
474:131.175
293:PubChem
252:464584
198:DB04419
54:Caprine
1166:(DHPG)
1136:(PABA)
1042:Health
1000:toxins
998:human
984:(GABA)
926:Plant
876:
741:valine
707:sulfur
689:. In
659:chiral
595:verify
592:
555:Lysine
415:SMILES
267:C01933
178:401917
126:B00369
118:3DMet
31:Names
1296:types
1127:Other
1088:(AIB)
641:CH(NH
390:InChI
149:ChEBI
97:JSmol
874:PMID
697:Uses
333:UNII
306:9475
278:MeSH
258:KEGG
849:doi
833:doi
812:doi
681:on
645:)CO
633:(CH
623:Nle
359:EPA
296:CID
1357::
1298::
870:11
868:.
808:56
806:.
802:.
513:)
506:(p
453:13
41:(2
1040:/
911:e
904:t
897:v
880:.
851::
835::
820:.
814::
647:2
643:2
639:3
637:)
635:2
631:3
590:Y
511:a
508:K
462:2
459:O
456:N
450:H
447:6
444:C
361:)
357:(
99:)
86:)
84:S
43:S
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