The synthesis of one enantiomer of the α-methyl-trans-cyclopropane unit of mycolic acids

Tetrahedron

Volumn 62, Issue 20, 2006, Pages 4851-4862

  Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a   Mohammed, Hayder ^a   Roberts, Evan ^a   Clegg, William ^b  

^a BANGOR UNIVERSITY   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; MYCOLIC ACID;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 33646070297     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.007     Document Type: Article

References (59)

1. Minnikin D.E. In: Ratledge C., and Stansford J. (Eds). The Biology of the Mycobacteria (1982), Academic, London 95
2. Brennan P.J., and Nikaido H. Annu. Rev. Biochem. 64 (1995) 29-63
3. Asselineau J., and Laneelle G. Front. Biosci. 3 (1998) 164-174
4. Minnikin D.E., Kremer L., Dover L.G., and Besra G.S. Chem. Biol. 9 (2002) 545-553
5. Barry C.E., Lee R.E., Mdluli K., Sampson A.E., Schroeder B.G., Slayden R.A., and Yuan Y. Prog. Lipid Res. 37 (1998) 143-179
6. Minnikin D.E., and Polgar N. J. Chem. Soc., Chem. Commun. (1967) 916-918
7. Minnikin D.E., and Polgar N. J. Chem. Soc., Chem. Commun. (1967) 1172-1177
8. George K.M., Yuan Y., Sherman D.S., and Barry C.E. J. Biol. Chem. 272 (1995) 27292-27298
9. Dobson G.; Minnikin D. E.; Minnikin S. M.; Parlett J. H.; Goodfellow M. Chemical Methods in Bacterial Systematics; Minnikin, D. E., Goodfellow, M., Eds.; Academic: London; 237 pp.
10. Minnikin D.E., and Polgar N. J. Chem. Soc., Chem. Commun. (1967) 1172-1174
11. Minnikin D.E., Minnikin S.M., Goodfellow M., and Stanford J.L. J. Gen. Microbiol. 128 (1982) 817-822
12. Yuan Y., Crane D.C., Musser J.M., Sreevatsan S., and Barry C.E. J. Biol. Chem. 272 (1997) 10041-10049
13. Lacave C., Lanéelle M.-A., Daffé M., Montrozier H., Rols M.-P., and Asselineau C. Eur. J. Biochem. 163 (1987) 369-378
14. Daffé M., Lanéelle M.-A., and Lacave C. Res. Microbiol. 142 (1991) 397-403
15. Dubnau E., Lanéelle M.-A., Soares S., Benichou A., Vaz T., Prome D., Daffé M., and Quemard A. Mol. Microbiol. 23 (1997) 313-322
16. Laval F., Laneelle M.-A., Deon C., Monsarrat B., and Daffe M. Anal. Chem. 73 (2001) 4537-4544
17. Watanabe M., Aoyagi Y., Mitome H., Fujita T., Naoki H., Ridell M., and Minnikin D.E. Microbiology 148 (2002) 1881-1902
18. Watanabe M., Aoyagi Y., Ridell M., and Minnikin D.E. Microbiology 147 (2001) 1825-1837
19. Watanabe M., Ohta A., Sasaki S.-I., and Minnikin D.E. J. Bacteriol. 181 (1999) 2293-2297
20. Fujita Y., Naka T., Doi T., and Yano I. Microbiology 151 (2005) 1443-1452 Wax esters have also been shown to be present in trehalose monomycolates from M. avium-intracellulare, M. phlei and M. flavescens, though it is not clear whether these contain α-methyl-trans-cyclopropanes
21. See e.g.
22. He H., Oka S., Yamamura Y., Kusunose E., Kusunose M., and Yano I. Microbiol. Immunol. 76 (1991) 201-204
23. Maekura R., Nakagawa M., Nakamura Y., Hiraga T., Yamamura Y., Ito M., Ueda E., Yano S., He H., Oka S., Kashima K., and Yano I. Am. Rev. Respir. Dis. 148 (1993) 997-1001
24. Pan J., Fujiwara N., Oka R., Ogura T., and Yano I. Microbiol. Immunol. 43 (1999) 863-869
25. Liu J., Barry C.E., Besra G.S., and Nikaido H. J. Biol. Chem. 271 (1996) 29545-29551
26. Asselineau C., and Asselineau J. Bull. Soc. Chim. Fr. (1966) 1992-1999
27. Tocanne J.F., and Asselineau C. Bull. Soc. Chim. Fr. (1968) 4519-4525
28. Asselineau C., Tocanne G., and Tocanne J.F. Bull. Soc. Chim. Fr. (1970) 1455-1459
29. Lacave C., Lanéelle M.-A., Daffé M., Montrozier H., Rols M.-P., and Asselineau C. Eur. J. Biochem. 163 (1987) 369-378
30. Al-Dulayymi J.R., Baird M.S., and Roberts E. J. Chem. Soc., Chem. Commun. (2003) 228-229
31. Al-Dulayymi J.R., Baird M.S., and Roberts E. Tetrahedron 61 (2005) 11939-11951
32. Al-Dulayymi J.R., Baird M.S., and Roberts E. Tetrahedron Lett. 41 (2000) 7107-7110
33. Astola J., Munoz M., Sempere M., Coll P., Luquin M., and Valero-Guillen P.L. Microbiology 148 (2002) 3119-3127
34. See e.g.
35. Lee R.E., Armour J.W., Takayama K., Brennan P.J., and Besra G.S. Biochim. Biophys. Acta 1346 (1997) 275-284
36. Grogan D.W., and Cronan J.E. Microbiol. Mol. Biol. Rev. 61 (1997) 429-441
37. Asselineau C., Asselineau J., Lanéelle G., and Lanéelle M.-A. Prog. Lipid Res. 41 (2002) 501-523
38. Kremer L., Baulard A.R., and Besra G.S. In: Hatfull G.F., and Jacobs W.R. (Eds). Molecular Genetics of Mycobacteria (2000), American Soc. Microbiology, Washington, DC 173
39. Yuan Y., Mead D., Schroeder B.G., Yu Y.Q., and Barry C.E. J. Biol. Chem. 273 (1998) 21282-21290
40. Yuan Y., Crane D.C., Musser J.M., Sreevatsan S., and Barry C.E. J. Biol. Chem. 272 (1997) 10041-10049
41. Yuan Y., and Barry C.E. Proc. Natl. Acad. Sci. 93 (1996) 12828-12833
42. Schroeder B.G., and Barry C.E. Bioorg. Chem. 29 (2001) 164-177
43. Glickman M.S., Cahill S.M., and Jacobs W.R. J. Biol. Chem. 276 (2001) 2228-2233
44. Morikawa T., Sasaki H., Hanai R., Shibuya A., and Taguchi T. J. Org. Chem. 59 (1994) 97-103
45. Martin B.K.D., Mann J., and Sageot O.A. J. Chem. Soc., Perkin Trans. 1 (1999) 2455-2460
46. Coxon G.D., Al-Dulayymi J.R., Baird M.S., Knobl S., Roberts E., and Minnikin D.E. Tetrahedron: Asymmetry (2003) 1211-1222 See also, e.g., reference 25.
47. Grandjean D., Pale P., and Chuche J. Tetrahedron 47 (1991) 1215-1230
48. Baudin J.B., Hareau G., Julia S.A., and Ruel O. Tetrahedron Lett. 32 (1991) 1175-1178
49. Baudin J.B., Hareau G., Julia S.A., and Ruel O. Bull. Soc. Chim. Fr. (1993) 336-357
50. Baudin J.B., Hareau G., Julia S.A., Lorne R., and Ruel O. Bull. Soc. Chim. Fr. (1993) 856-878
51. See e.g.,. Blakemore P.R., Cole W.J., Kocienski P.J., and Morley A. Synlett (1998) 26-28
52. Blakemore P.R., Cole W.J., Kocienski P.J., and Morley A. Synlett (1999) 1209-1215
53. Kocienski P.J., Bell A., and Blakemore P.R. Synlett (2000) 356-366
54. Jorgenson M.J. J. Am. Chem. Soc. 91 (1969) 6432-6443
55. Barloy-Da Silva C., Benkonider A., and Pale P. Tetrahedron Lett. 41 (2000) 3077-3081
56. Mitome H., Miyaoka H., Nakano M., and Yamada Y. Tetrahedron Lett. 36 (1995) 8231-8234
57. Honda T., Katoh M., and Yamane S.-I. J. Chem. Soc., Perkin Trans. 1 (1996) 2291
58. Fujimoto Y., Ohhana M., Terasawa T., and Ikekawa N. Tetrahedron Lett. 26 (1985) 3239-3242
59. See also,. Cossy J., Blanchard N., Defoosseux M., and Meyer C. Angew. Chem., Int. Ed. 41 (2002) 2144-2146