101:
1536:
1546:
707:
Gler, M. T.; Skripconoka, V.; Sanchez-Garavito, E.; Xiao, H.; Cabrera-Rivero, J. L.; Vargas-Vasquez, D. E.; Gao, M.; Awad, M.; Park, S. K.; Shim, T. S.; Suh, G. Y.; Danilovits, M.; Ogata, H.; Kurve, A.; Chang, J.; Suzuki, K.; Tupasi, T.; Koh, W. J.; Seaworth, B.; Geiter, L. J.; Wells, C. D. (2012).
201:, the different homologues from the natural mixture could be obtained in pure form and tested for biological activity. One subclass proved to be a very good suppressor of asthma, through a totally new mode of action. These compounds are now under further investigation. A second subclass triggered a
355:
mycolic acids exist. The first has between 28 and 46 carbon atoms with either 0 or 1 unsaturated bonds. The second has between 34 and 54 carbon atoms with between 0 and 4 unsaturated bonds. Sutcliffe (1998) has proposed that they are linked to the rest of the cell wall by
671:
Korf, J. E.; Pynaert, G.; Tournoy, K.; Boonefaes, T.; Van
Oosterhout, A.; Ginneberge, D.; Haegeman, A.; Verschoor, J. A.; De Baetselier, P.; Grooten, J. (2006). "Macrophage Reprogramming by Mycolic Acid Promotes a Tolerogenic Response in Experimental Asthma".
55:; the name arises from the filamentous appearance their presence gives Mycobacteriales under high magnification. The presence of mycolic acids in the cell wall also gives Mycobacteriales a distinct gross morphological trait known as "
224:
The exact structure of mycolic acids appears to be closely linked to the virulence of the organism, as modification of the functional groups of the molecule can lead to an attenuation of growth
179:
Pks13 between the α-branch and the meromycolate chain before a final reduction by the enzyme corynebacterineae mycolate reductase A (CmrA) to generate the mycolic acid; and
116:
produces three main types of mycolic acids: alpha-, methoxy-, and keto-. Alpha-mycolic acids make up at least 70% of the mycolic acids of the organism and contain several
124:
groups, constitute between 10% and 15% of the mycolic acids in the organism. The remaining 10% to 15% of the mycolic acids are keto-mycolic acids, which contain several
246:(OPC-67683), a new agent derived from the nitro-dihydro-imidazooxazole class of compounds that inhibits mycolic acid synthesis, can increase the rate of sputum
583:"The Mycobacterium tuberculosis FAS-II condensing enzymes: Their role in mycolic acid biosynthesis, acid-fastness, pathogenesis and in future drug development"
135:
with unique properties that defy medical treatment. They make the organism more resistant to chemical damage and dehydration, and limit the effectiveness of
193:
The mycolic acids show interesting inflammation controlling properties. A clear tolerogenic response was promoted by natural mycolic acids in experimental
187:
51:. They form the major component of the cell wall of many Mycobacteriales species. Despite their name, mycolic acids have no biological link to
158:. The pathway and enzymes have been elucidated and reported in detail. Five distinct stages are involved. These were summarised as follows:
85:
atoms. The exact number of carbons varies by species and can be used as an identification aid. Most mycolic acids also contain various
430:
Lambert, PA (2002). "Cellular impermeability and uptake of biocides and antibiotics in Gram-positive bacteria and mycobacteria".
632:"The Reductase That Catalyzes Mycolic Motif Synthesis Is Required for Efficient Attachment of Mycolic Acids to Arabinogalactan"
1475:
1242:
982:
251:
190:
enzyme, often designated as mtFabH. Novel inhibitors of this enzyme could potentially be used as therapeutic agents.
1232:
1159:
630:
Lea-Smith, David J; James S. Pyke; Dedreia Tull; Malcolm J. McConville; Ross L. Coppel; Paul K. Crellin (2007).
1356:
1087:
796:
Barry III, C. E.; Lee, R. E.; Mdluli, K.; Sampson, A. E.; Schroeder, B. G.; Slayden, R. A.; Yuan, Y. (1998).
182:
Transfer of mycolic acids to arabinogalactan and other acceptors such as trehalose via the antigen 85 complex
186:
The fatty acid synthase-I and fatty acid synthase-II pathways producing mycolic acids are linked by the
1197:
43:
1549:
265:
Mycolic acids with different sizes and chemical modifications are found throughout
Mycobacteriales.
1351:
1274:
1237:
1033:
954:
829:
Nishiuchi, Y.; Baba, T.; Yano, I. (2000). "Mycolic acids from
Rhodococcus, Gordonia, and Dietzia".
56:
1575:
1427:
1346:
1325:
975:
172:
Introduction of functional groups to the meromycolate chain by numerous cyclopropane synthases;
279:
species, which display great variation in length and modifications. Modifications not seen in
1467:
1109:
901:"Unsupported planar lipid membranes formed from mycolic acids of Mycobacterium tuberculosis"
1570:
1307:
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1165:
1003:
535:
348:
8:
1432:
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71:
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475:"Pathway to Synthesis and Processing of Mycolic Acids in Mycobacterium tuberculosis"
459:
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443:
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389:
86:
891:
858:
Sutcliffe, I. C. (1998). "Cell envelope composition and organisation in the genus
524:"Flux Balance Analysis of Mycolic Acid Pathway: Targets for Anti-Tubercular Drugs"
1480:
1379:
1264:
1140:
1070:
1023:
548:
490:
357:
197:. The natural extracts are however chemically heterogeneous and inflammatory. By
112:
31:
378:"Commentary: Genome-Based Taxonomic Classification of the Phylum Actinobacteria"
1135:
1099:
685:
418:
Mycolic acids are important constituents of the cell envelopes of most members.
202:
169:
Synthesis of the C56 fatty acids by FAS-II providing the meromycolate backbone;
875:
100:
1564:
1489:
1374:
1330:
1302:
1293:
1283:
1259:
1155:
752:
Marrakchi, Hedia; Lanéelle, Marie-Antoinette; Daffé, Mamadou (January 2014).
394:
151:
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883:
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117:
48:
821:
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339:
234:
in genes responsible for mycolic acid synthesis exhibit altered cording.
218:
136:
917:
899:
Langford, K. W.; Penkov, B.; Derrington, I. M.; Gundlach, J. H. (2010).
162:
Synthesis of the C26 saturated straight chain fatty acids by the enzyme
1514:
1499:
1417:
1150:
275:
Most attention have been traditionally devoted to the mycolic acids of
147:
139:
78:
23:
581:
Bhatt, A.; Molle, V.; Besra, G. S.; Jacobs, W. R.; Kremer, L. (2007).
1509:
1340:
1298:
1210:
1104:
243:
27:
16:
798:"Mycolic acids: Structure, biosynthesis and physiological functions"
797:
154:. Mycolate biosynthesis is crucial for survival and pathogenesis of
1018:
995:
706:
347:. They contain no functional groups, but instead may have several
231:
214:
206:
143:
38:
1448:
1412:
1048:
226:
121:
898:
1494:
1249:
194:
125:
82:
52:
166:-I (FAS-I) to provide the α-alkyl branch of the mycolic acids;
1422:
335:
75:
34:
670:
210:
710:"Delamanid for Multidrug-Resistant Pulmonary Tuberculosis"
674:
American
Journal of Respiratory and Critical Care Medicine
795:
146:. Mycolic acids also allow the bacterium to grow inside
521:
751:
754:"Mycolic Acids: Structures, Biosynthesis, and Beyond"
580:
213:), so studies are ongoing to use this subclass as an
120:
rings. Methoxy-mycolic acids, which contain several
242:
An international multi-centre study has proved that
92:
828:
472:
188:beta-ketoacyl-(acyl-carrier-protein) synthase III
59:". Mycolic acids were first isolated by Stodola
1562:
522:Raman, K.; Rajagopalan, P.; Chandra, N. (2005).
976:
473:Takayama, K.; Wang, C.; Besra, G. S. (2005).
81:. Each molecule contains between 60 and 90
747:
745:
990:
983:
969:
953:at the U.S. National Library of Medicine
926:
916:
857:
769:
725:
647:
598:
557:
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498:
403:
393:
257:
742:
99:
429:
175:Condensation reaction catalysed by the
70:Mycolic acids are composed of a longer
1563:
150:, effectively hiding it from the host
964:
376:Gupta, Radhey S. (22 February 2019).
375:
343:differ in several ways from those of
237:
47:, the causative agent of the disease
1545:
334:The mycolic acids of members of the
13:
831:Journal of Microbiological Methods
789:
14:
1587:
944:
287:Double bonds (cis and trans), in
252:multi-drug-resistant tuberculosis
1544:
1535:
1534:
600:10.1111/j.1365-2958.2007.05761.x
268:
1233:Bacterial cellular morphologies
714:New England Journal of Medicine
636:Journal of Biological Chemistry
291:(with a branch from UmaA1) and
771:10.1016/j.chembiol.2013.11.011
700:
664:
623:
574:
515:
466:
444:10.1046/j.1365-2672.92.5s1.7.x
423:
369:
327:
1:
905:The Journal of Lipid Research
843:10.1016/S0167-7012(99)00116-5
814:10.1016/S0163-7827(98)00008-3
479:Clinical Microbiology Reviews
363:
351:. Two different profiles of
230:. Further, individuals with
549:10.1371/journal.pcbi.0010046
491:10.1128/CMR.18.1.81-101.2005
7:
106:Mycobacterium tuberculosis.
74:chain with a shorter alpha-
63:in 1938 from an extract of
10:
1592:
1476:Bacteria (classifications)
1198:Primary nutritional groups
802:Progress in Lipid Research
686:10.1164/rccm.200507-1175OC
528:PLOS Computational Biology
44:Mycobacterium tuberculosis
1530:
1461:
1441:
1393:
1282:
1273:
1225:
1118:
1056:
1042:
1002:
382:Frontiers in Microbiology
1352:Bacterial outer membrane
955:Medical Subject Headings
395:10.3389/fmicb.2019.00206
876:10.1023/A:1001747726820
864:Antonie van Leeuwenhoek
758:Chemistry & Biology
1347:Gram-negative bacteria
1326:Gram-positive bacteria
649:10.1074/jbc.M608686200
587:Molecular Microbiology
108:
1202:Substrate preference
727:10.1056/NEJMoa1112433
254:(MDRTB) at 2 months.
131:Mycolic acids impart
103:
1183:Microbial metabolism
1433:Non-motile bacteria
1029:Pathogenic bacteria
918:10.1194/jlr.M012013
642:(15): 11000–11008.
540:2005PLSCB...1...46R
177:polyketide synthase
164:fatty acid synthase
1362:Lipopolysaccharide
248:culture conversion
238:Clinical relevance
109:
1558:
1557:
1457:
1456:
1403:Bacterial capsule
1369:Periplasmic space
1336:Lipoteichoic acid
1221:
1220:
1193:Microbial ecology
1188:Nitrogen fixation
720:(23): 2151–2160.
349:unsaturated bonds
306:-epoxy group, in
205:immune response (
199:organic synthesis
104:Mycolic acids in
93:Mycolic acids of
87:functional groups
1583:
1548:
1547:
1538:
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1486:Former groupings
1280:
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1131:Human microbiome
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1053:
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808:(2–3): 143–179.
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593:(6): 1442–1454.
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432:J Appl Microbiol
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297:ω-1 methoxy, in
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1481:Bacterial phyla
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1380:Arabinogalactan
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1114:
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1024:Lysogenic cycle
1005:
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358:arabinogalactan
345:M. tuberculosis
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281:M. tuberculosis
273:
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260:M. tuberculosis
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156:M. tuberculosis
133:M. tuberculosis
113:M. tuberculosis
98:
95:M. tuberculosis
65:M. tuberculosis
32:Mycobacteriales
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1100:Microaerophile
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37:, a group of
36:
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26:found in the
25:
21:
20:Mycolic acids
1520:Mendosicutes
1505:Gracilicutes
1485:
1385:Mycolic acid
1384:
1375:Mycobacteria
1373:
1345:
1324:
1260:Coccobacilli
1160:in pregnancy
1126:Extremophile
1110:Aerotolerant
1044:Biochemistry
1006:microbiology
992:Microbiology
951:Mycolic+Acid
908:
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764:(1): 67–85.
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72:beta-hydroxy
69:
64:
60:
49:tuberculosis
42:
19:
18:
1571:Fatty acids
1408:Slime layer
1088:Facultative
1076:Facultative
860:Rhodococcus
438:: 46S–54S.
360:molecules.
353:Rhodococcus
340:Rhodococcus
329:Rhodococcus
219:vaccination
148:macrophages
140:antibiotics
137:hydrophilic
24:fatty acids
1565:Categories
1515:Mollicutes
1510:Firmicutes
1500:Prokaryota
1418:Glycocalyx
1243:plasticity
1206:Lipophilic
1059:preference
1034:Resistance
837:(1): 1–9.
534:(5): e46.
364:References
79:side chain
28:cell walls
1468:evolution
1442:Composite
1341:Endospore
1299:Cell wall
1275:Structure
1166:Placental
1105:Nanaerobe
1083:Anaerobic
1014:Infection
283:include:
244:delamanid
232:mutations
22:are long
1540:Category
1463:Taxonomy
1396:envelope
1286:envelope
1176:Salivary
1093:Obligate
1071:Obligate
1019:Exotoxin
996:Bacteria
937:21076119
884:10068788
851:10739337
780:24374164
736:22670901
694:16675779
658:17308303
617:32586686
609:17555433
568:16261191
509:15653820
460:24067247
452:12000612
414:30853945
322:M. avium
299:M. alvei
293:M. alvei
215:adjuvant
203:cellular
144:biocides
128:groups.
39:bacteria
1550:Commons
1449:Biofilm
1428:Fimbria
1413:S-layer
1394:Outside
1255:Bacilli
1171:Uterine
1156:Vaginal
1066:Aerobic
1049:ecology
1004:Medical
928:3023547
822:9829124
559:1246807
536:Bibcode
405:6395429
388:: 206.
258:Beyond
227:in vivo
122:methoxy
57:cording
1495:Monera
1265:Spiral
1057:Oxygen
957:(MeSH)
935:
925:
892:785035
890:
882:
849:
820:
778:
734:
692:
656:
615:
607:
566:
556:
507:
500:544180
497:
458:
450:
412:
402:
195:asthma
126:ketone
83:carbon
61:et al.
1423:Pilus
1377:only:
1357:Porin
1349:only:
1328:only:
1250:Cocci
1226:Shape
1146:Mouth
1119:Other
888:S2CID
613:S2CID
456:S2CID
336:genus
304:trans
76:alkyl
53:fungi
35:taxon
1466:and
1284:Cell
1151:Skin
1141:Lung
1047:and
933:PMID
880:PMID
847:PMID
818:PMID
776:PMID
732:PMID
690:PMID
654:PMID
605:PMID
564:PMID
505:PMID
448:PMID
410:PMID
217:for
211:Th17
209:and
142:and
1318:DAP
1313:NAG
1308:NAM
1136:Gut
923:PMC
913:doi
872:doi
862:".
839:doi
810:doi
766:doi
722:doi
718:366
682:doi
678:174
644:doi
640:282
595:doi
554:PMC
544:doi
495:PMC
487:doi
440:doi
400:PMC
390:doi
318:cis
316:or
250:in
207:Th1
30:of
1567::
1488::
1301::
994::
931:.
921:.
909:52
907:.
903:.
886:.
878:.
868:74
866:.
845:.
835:40
833:.
816:.
806:37
804:.
800:.
774:.
762:21
760:.
756:.
744:^
730:.
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688:.
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652:.
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603:.
591:64
589:.
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384:.
380:.
221:.
89:.
67:.
1162:)
1158:(
984:e
977:t
970:v
939:.
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442::
392::
314:S
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