The synthesis of a single enantiomer of a major α-mycolic acid of M. tuberculosis

Tetrahedron

Volumn 61, Issue 50, 2005, Pages 11939-11951

  Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a   Roberts, Evan ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

Tuberculosis mycolic acid

Indexed keywords

CYCLOPROPANE; MYCOLIC ACID;

ARTICLE; BACTERIAL CELL WALL; CHEMICAL STRUCTURE; ENANTIOMER; MYCOBACTERIUM TUBERCULOSIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS;

EID: 27844453864     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.056     Document Type: Article

References (67)

1. P.J. Brennan, and H. Nikaido Annu. Rev. Biochem. 64 1995 29 63
2. N. Qureshi, K. Takayama, H.C. Jordi, and H.K. Schnoes J. Biol. Chem. 253 1978 5411 5417
3. D.E. Minnikin, M. Daffe, and P. Draper Adv. Microbial Phys. 39 1998 131 203
4. D.E. Minnikin, L. Kremer, L.G. Dover, and G.S. Besra Chem. Biol. 9 2002 545
5. D.E. Minnikin, and N. Polgar J. Chem. Soc., Chem. Commun. 312-314 1967 916 918 (See also pp 1172-1174)
6. Y. Yuan, D.C. Crane, J.M. Musser, S. Sreevatsan, and C.E. Barry J. Biol. Chem. 272 1997 10041 10049
7. K.M. George, Y. Yuan, D.S. Sherman, and C.E. Barry J. Biol. Chem. 272 1995 27292 27298
8. G. Dobson, D.E. Minnikin, S.M. Minnikin, J.H. Parlett, M. Goodfellow, M. Ridell, and M. Magnusson D.E. Minnikin M. Goodfellow Chemical Methods in Bacterial Systematics 1985 Academic London 237
9. M.S. Glickman, S.M. Cahill, and W.R. Jacobs J. Biol. Chem. 276 2001 2228 2233
10. R. Toubiana, B.C. Desh, J. Defaye, G. Mompon, and M.-J. Toubiana Carbohydr. Res. 44 1975 308 312
11. J.-C. Prome, C. Lacave, A. Ahibo-Coffy, and A. Savagnac Eur. J. Biochem. 63 1976 543 552
12. H.H. Baer, and X. Wu Carbohydr. Res. 245 1993 347
13. See, for example, I. Matsunaga, S. Oka, N. Fujiwara, and I. Yano J. Biochem. 120 1996 663 670
14. M. Parant, F. Audibert, F. Parant, L. Chelid, E. Soler, J. Polonsky, and E. Lederer Infect. Immunol. 20 1978 12 19
15. A. Tanaka, K. Sugiwara, I. Azuma, Y. Yamamura, M. Kato, and M.B. Goren Infect. Immun. 13 1976 776 781
16. E. Sueoka, S. Nishiwaki, S. Okabe, N. Iida, M. Suganuma, I. Yano, K. Aoki, and H. Fujiki Jpn. J. Cancer Res. 86 1995 749 755
17. I. Yano Kekkaku 73 1998 37 42
18. See, for example, J. Pan, N. Fujiwara, S. Oka, R. Maekura, T. Ogura, and I. Yano Microbiol. Immunol. 43 1999 863 869
19. N. Fujiwara, J. Pan, K. Enomoto, Y. Terano, T. Honda, and I. Yano FEMS Immunol. Med. Microbiol. 24 1999 141 149
20. H. He, S. Oka, Y. Han, Y. Yamamura, E. Kusunose, M. Kusunose, and I. Yano Microbiol. Immunol. 76 1991 201 204
21. R. Maekura, M. Nakagawa, Y. Nakamura, T. Higara, Y. Yamamura, M. Ito, E. Ueda, S. Yano, H. He, S. Oka, K. Kashima, and I. Yano Am. Rev. Respir. Dis. 148 1993 997 1001
22. L. Wang, S. Izumi, H. He, N. Fujiwara, N. Saita, I. Yano, K. Kobayashi, and N. Tatsumi Jpn. J. Lepr. 68 1999 165 174
23. N. Fujiwara, S. Oka, M. Ide, K. Kashima, T. Honda, and I. Yano Microbiol. Immunol. 43 1999 785 793
24. See, for example, W.J. Gensler, and J.P. Marshall Chem. Phys. Lipids 19 1977 128 143
25. For the analysis of mycolic acids see, for example, M. Watanabe, Y. Aoyagi, H. Mitome, T. Fujita, H. Naoki, M. Ridell, and D.E. Minnikin Microbiology 148 2002 1881
26. M. Watanabe, Y. Aoyagi, M. Ridell, and D.E. Minnikin Microbiology 147 2001 1825
27. D.E. Minnikin, L. Kremer, L.G. Dover, and G.S. Besra Chem. Biol. 9 2002 545
28. C. Lacave, M.-A. Lanéelle, M. Daffé, H. Montrozier, M.-P. Rols, and C. Asselineau Eur. J. Biochem. 163 1987 369
29. C. Asselineau, J. Asselineau, and G. Tocanne Bull. Soc. Chim. Fr. 1966 1992
30. M. Daffé, M.A. Lanéelle, and C. Lacave Res. Microbiol. 142 1991 397 403
31. E. Dubnau, M.-A. Lanéelle, S. Soares, A. Benichou, T. Vaz, D. Prome, J.C. Prome, M. Daffé, and A. Quemard Mol. Microbiol. 23 1997 313
32. See, for example, R.E. Lee, J.W. Armour, K. Takayama, P.J. Brennan, and G.S. Besra Biochim. Biophys. Acta 1346 1997 275 284
33. D.W. Grogan, and J.E. Cronan Microbiol. Mol. Biol. Rev. 61 1997 429 441
34. C. Asselineau, J. Asselineau, G. Lanéelle, and M.-A. Lanéelle Prog. Lipid Res. 41 2002 501
35. L. Kremer, A.R. Baulard, and G.S. Besra G.F. Hatfull W.R. Jacobs Molecular Genetics of Mycobacteria 2000 American Society for Microbiology Washington, DC 173 190
36. Y. Yuan, D. Mead, B.G. Schroeder, Y.Q. Zhu, and C.E. Barry J. Biol. Chem. 273 1998 21282 21290
37. Y. Yuan, and C.E. Barry Proc. Nat. Acad. Sci. U.S.A. 93 1996 12828 12833
38. W.J. Gensler, J.P. Marshall, J.J. Langone, and J.C. Chen J. Org. Chem. 42 1977 118 125
39. M.S. Baird, J.R. Al Dulayymi, and E. Roberts Tetrahedron Lett. 41 2000 7107 7110
40. E. Dubneau, M.-A. Laneelle, S. Soares, A. Benichou, T. Vaz, D. Prome, J.-C. Prome, M. Daffe, and A. Quemard Mol. Microbiol. 23 1997 313 322
41. D. Grandjean, P. Pale, and J. Cuche Tetrahedron 47 1991 1215
42. A.P. Krapcho, J.R. Larson, and J.M. Eldridge J. Org. Chem. 42 1977 3749 3753
43. J.B. Baudin, G. Hareau, S.A. Julia, and O. Ruel Tetrahedron Lett. 32 1991 1175 1178
44. J.R. Blakemore, P.J. Kocienski, S. Marzcak, and J. Wicha Synthesis 1999 1209 1215
45. N.D. Smith, P.J. Kocienski, and S.D.A. Street Synthesis 1996 652 666
46. Y. Kitano, Y. Kobayashi, and F. Sato J. Chem. Soc., Chem. Commun. 1985 498 499
47. M. Utaka, H. Higashi, and A. Takeda J. Chem. Soc., Chem. Commun. 1987 1368 1369
48. Prepared from (R)-aspartic acid based on, J.A. Frick, J.B. Klassen, A. Bathe, J.M. Abramson, and H. Rappoport Synthesis 1992 621
49. T. Fujisawa, A. Fujimura, and F. Sato Bull. Chem. Soc. Jpn. 61 1988 1273 1279
50. W. Jorgensen J. Am. Chem. Soc. 91 1969 6430 6443
51. 2
52. G.D. Coxon, S. Knobl, E. Roberts, M.S. Baird, J.R. Al Dulayymi, and D.E. Minnikin Tetrahedron: Asymmetry 14 2003 1211 1222
53. A. Watanabe Bull. Chem. Soc. Jpn. 36 1963 336 340
54. J.-J. Delpeuch Bull. Soc. Chim. Fr. 1966 1631
55. L. Bricard, and G. Kunesch Synth. Commun. 23 18 1993 2547
56. D. Bai, Y. Bo, and Q. Zhou Tetrahedron Lett. 1990 2161 2164
57. This has previously been prepared by reduction of the corresponding acid or its esters (Watanabe, A Bull. Chem. Soc. Jpn., 1961, 34, 398-402),
58. from the corresponding alkene or alkyne by hydroboration (Brown, H. C.; Iyer, R. R.; Bhat, N. G. Racherla, U. S.; Brown, C. A. Tetrahedron, 1992, 48, 9187)
59. or from tetracos-10-yn-1-ol (Menger, F. M.; Yamasaki, Y. J. Am. Chem. Soc. 1993, 115, 3840).
60. This has previously been prepared from the alcohol by reaction with HBr (Lukes, C. Collect. Czech. Chem. Commun., 1958, 23, 497, 500)
61. 35
62. W. Gensler, I. Alam, R.S. Prasad, A.I. Radhakrishnan, and A.P.C. Laudhun Tetrahedron 35 1979 2595 2600
63. J.A. Frick, J.B. Klassen, A. Bathe, J.M. Abramson, and H. Rapoport Synthesis 1992 621 623
64. A. Sharma, and S. Chattopadhyay J. Org. Chem. 63 1998 6128
65. M. Wolfgang, H. Clemensk, S. Juergen, and J.A. Gladysz Synthesis 8 2003 1279
66. 35
67. G. Linstrumelle, J.K. Krieger, and G.M. Whiteside Org. Synth. 55 1976 103 113