The first syntheses of single enantiomers of the major methoxymycolic acid of Mycobacterium tuberculosis

Tetrahedron

Volumn 63, Issue 12, 2007, Pages 2571-2592

  Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a   Roberts, Evan ^a   Deysel, Madrey ^b   Verschoor, Jan ^b  

^a BANGOR UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF PRETORIA   (South Africa)

Author keywords

Methoxymycolic acids; Mycobacterium tuberculosis

Indexed keywords

(2,2 DIMETHYL[1,3]DIOXOLAN 4 YL)ACRYLIC ACID METHYL ESTER; (2,2 DIMETHYL[1,3]DIOXOLAN 4 YL)BUTAN 1 OL; (2,2 DIMETHYL[1,3]DIOXOLAN 4 YL)BUTYRALDEHYDE; (2,2 DIMETHYL[1,3]DIOXOLAN 4 YL)BUTYRIC ACID ETHYL ESTER; (2,2 DIMETHYL[1,3]DIOXOLAN 4 YL)BUTYRIC ACID METHYL ESTER; 1,3 DIOXOLANE DERIVATIVE; 2 (1 METHYLNONADECYL)OXIRANE; 2 (8 METHOXY 9 METHYLHEPTACOSYLOXY)TETRAHYDROPYRAN; 2,2 DIMETHYL 4 (1 METHYLNONADECYL) [1,3]DIOXOLANE; 2,2 DIMETHYLPROPIONIC ACID 16 METHOXY 17 METHYLPENTATRIACONTYL ESTER; 3 METHYLHENICOSANE 1,2 DIOL; 5 (16 METHOXY 17 METHYLPENTATRIACONTANE 1 SULFONYL) 1 PHENYL 1H TETRAZOLE; 5 (16 METHOXY 17 METHYLPENTATRIACONTYL 1 SULFANYL) 1 PHENYL 1H TETRAZOLE; 5 (6 BROMOHEXANE 1 SULFONYL) 1 PHENYL 1H TETRAZOLE; 5 (HEXADECANE 1 SULFONYL) 1 PHENYL 1H TETRAZOLE; 5 HEXADECYLSULFANYL 1 PHENYL 1H TETRAZOLE; 6 (1 PHENYL 1H TETRAZOL 5 YLSULFANYL)HEXAN 1 OL; 8 METHOXY 9 METHYLHEPTACOSAN 1 OL; 9 METHYL 1 (TETRAHYDROPYRAN 2 YLOXY)HEPTACOSAN 8 OL; ALPHA MYCOLIC ACID; ESTER DERIVATIVE; ETHER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; METHOXYMYCOLIC ACID; MYCOLIC ACID; OXOMYCOLIC ACID; PROPIONIC ACID DERIVATIVE; PYRAN DERIVATIVE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; STEREOISOMERISM; STRUCTURAL HOMOLOGY;

MYCOBACTERIUM TUBERCULOSIS;

EID: 33846922093     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.007     Document Type: Article

References (49)

1. Minnikin D.E. In: Standford J. (Ed). The Biology of the Mycobacteria (1982), Academic, San Diego, CA 96-184
2. Barry C.E., Lee R.E., Mdluli K., Sampson A.E., Schoeder B.G., Slayden R.A., and Yuan Y. Prog. Lipid Res. 37 (1998) 143-179
3. Heath R.J., White S.W., and Rock C.O. Appl. Microbiol. Biotechnol. 58 (2002) 695-703
4. Watanabe M., Aoyagi Y., Mitome H., Fujita T., Naoki H., Ridell M., and Minnikin D.E. Microbiology 148 (2002) 1881-1902
5. Watanabe M., Aoyagi Y., Ridell M., and Minnikin D.E. Microbiology 147 (2001) 1825-1837
6. Minnikin D.E., and Polgar N. J. Chem. Soc., Chem. Commun. (1966) 648-649
7. J. Chem. Soc., Chem. Commun. (1967) 916-918 1172-1174
8. Asselineau C., Tocanne G., and Tocanne J.F. Bull. Soc. Chim. Fr. 4 (1970) 1455-1459
9. Lacave C., Lanéelle M.-A., Montrozier H., Rols M.-P., and Asselineau C. Eur. J. Biochem. 163 (1987) 369-378
10. Daffé M., Lanéelle M.A., and Guillen L.V. Eur. J. Biochem. 177 (1988) 339-340
11. Daffé M., Lanéelle M.A., and Lacave C. Res. Microbiol. 142 (1991) 397-403
12. Durand H., Welby M., Lanéelle G., and Tocanne J.-F. Eur. J. Biochem. 93 (1979) 103-112
13. Durand H., Gillois M., Tocanne J.-F., and Lanéelle G. Eur. J. Biochem. 94 (1979) 109-118
14. Moody D.B., Guy M.R., Grant E., Cheng T.-Y., Brenner M.B., Besra G.S., and Porcelli S.A. J. Exp. Med. 192 (2000) 965-976
15. Watanabe R., Yoo Y.C., Hata K., Mitobe M., Koike Y., Nishizawa M., Garcia D.M., Nobuchi Y., Hiroshi I., Yamada H., and Azuma I. Vaccine 17 (1999) 1484-1492
16. For a review, see:. Ryll R., Kumazawa Y., and Yano I. Microbiol. Immunol. 45 (2001) 801-811
17. Fujiwara N., Pan J., Enomoto K., Terano Y., Honda T., and Yano I. FEMS Immunol. Med. Microbiol. 24 (1999) 141-149
18. Fujiwara N., Oka S., Ide M., Kashima K., Honda T., and Yano I. Microbiol. Immunol. 43 (1999) 785-793
19. Pan J., Fujiwara N., Oka S., Maekura R., Ogura T., and Yano I. Microbiol. Immunol. 43 (1999) 863-869
20. Grant E.P., Beckman E.M., Bahar S.M., Degano M., Frederique D., Besra G.S., Wilson I.A., Porcelli S.A., Furlong S.T., and Brenner M.B. J. Immunol. 168 (2002) 3933-3940
21. Dubnau E., Lanéelle M.-A., Soares S., Benichou A., Vaz T., Promé D., Promé J.-C., Daffé M., and Quémard A. Mol. Microbiol. 23 (1997) 313-322
22. Dinnadayala P., Laval F., Raynaud C., Lemassu A., Lanéelle M.A., Lanéelle G., and Daffé M. J. Biol. Chem. 278 (2003) 7310-7319
23. Dubnau E., Chan J., Raynaud C., Mohan V.P., Lanéelle M.-A., Yu K., Quémard A., Smith I., and Daffé M. Mol. Microbiol. 36 (2000) 630-637
24. Yuan Y., Zhu Y.Q., Crane D.D., and Barry C.E. Mol. Microbiol. (1998) 1449-1458
25. Glickman M.S., Cox J.S., and Jacobs W.R. Mol. Cells 5 (2000) 717-727
26. Gao L.-Y., Laval F., Lawson E.H., Groger R.K., Woodruff A., Morisaki J.H., Cox J.S., Daffé M., and Brown E.J. Mol. Microbiol. 49 (2003) 1547-1563
27. Batawangala T., Shepherd D., Gadola S.D., Gibson K.J.C., Zaccai N.R., Fersht A.R., Besra G.S., Cerundolo V., and Jones E.Y. J. Immunol. 172 (2004) 2382-2388
28. Huang C.-c., Smith C.V., Glickman M.S., Jacobs W.R., and Sacchettini J.C. J. Biol. Chem. 277 (2002) 11559-11569
29. Miller D.J., Ouellette N., Evdokimova E., Savchenko A., Edwards A., and Anderson W.F. Protein Sci. 12 (2003) 1432-1442
30. Zeng Z.-H., Castano A.R., Segelke B.W., Stura E.A., Peterson P.A., and Wilson I.A. Science 277 (1997) 339-345
31. Gadola S.D., Zaccai N.R., Harlos K., Shepherd D., Castro-Palomino J.C., Ritter G., Schmidt R.R., Jones E.V., and Cerundolo V. Nat. Immunol. 3 (2002) 721-726
32. Al Dulayymi J.R., Baird M.S., and Roberts E. Tetrahedron 61 (2005) 11939-11951
33. Al Dulayymi J.R., Baird M.S., and Roberts E. Chem. Commun. (2003) 228-229
34. Al Dulayymi J.R., Baird M.S., Mohammed H., Roberts E., and Clegg W. Tetrahedron 62 (2006) 4851-4862
35. Al Dulayymi J.R., Baird M.S., and Roberts E. Tetrahedron Lett. 41 (2000) 7107-7110
36. Al Dulayymi J.R., Baird M.S., Roberts E., and Minnikin D.E. Tetrahedron 62 (2006) 11867-11890
37. Nilsson K., and Ullenius C. Tetrahedron 50 (1994) 13173-13180
38. Leonard J., Mohialdin S., Reed D., Ryan G., and Swain P.A. Tetrahedron 51 (1995) 12843-12858
39. Munakata R., Ueki T., Katakai H., Tako K.-i., and Tadano K.-i. Org. Lett. 19 (2001) 3029-3032
40. Munakata R., Katakai H., Ueki T., Kurosaka J., Tako K.-i., and Tadano K.-i. J. Am. Chem. Soc. 126 (2004) 11254-11267
41. Andrews G.C., Crawford T.C., and Bacon B.E. J. Org. Chem. 46 (1981) 2967-2977
42. Hubschwerlen C. Synthesis (1986) 962-964
43. Coxon G.D., Al Dulayymi J.R., Morehouse C., Brennan P.J., Besra G.S., Baird M.S., and Minnikin D.E. Chem. Phys. Lipids 127 (2004) 35-46
44. Nakahara Y., Beppu K., and Ogava T. Tetrahedron Lett. 22 (1981) 3197-3200
45. Linstrumelle G., Krieger J.K., and Whitesides G.M. Org. Synth. 55 (1976) 103-113
46. Toschi G., and Baird M.S. Tetrahedron 62 (2006) 3221-3227
47. Anderson R.J., Creighton M.M., and Peck R.L. J. Biol. Chem. 132 (1940) 675-693
48. Geiger W.B., and Anderson R.J. J. Biol. Chem. 131 (1939) 539-548
49. Minnikin D.E., Dobson G., Goodfellow M., Draper P., and Magnusson M. J. Gen. Microbiol. 131 (1985) 2013-2021