Synthesis of methyl β-D-arabinofuranoside 5-[1D (and L)-myo-inositol 1-phosphate], the capping motif of the lipoarabinomannan of Mycobacterium smegmatis

Carbohydrate Research

Volumn 317, Issue 1-4, 1999, Pages 110-118

  Désiré, Jérôme ^a   Prandi, Jacques ^a  

^a INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

Author keywords

D Arabinofuranoside; Lipoarabinomannan; Mycobacterium smegmatis; Sugar phosphates

Indexed keywords

ARABINOMANNAN; BACTERIAL POLYSACCHARIDE; SUGAR PHOSPHATE;

ARTICLE; CAPPING PHENOMENON; CARBOHYDRATE SYNTHESIS; DIASTEREOISOMER; GLYCOSYLATION; MYCOBACTERIUM SMEGMATIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

ANTIGENS, BACTERIAL; CARBOHYDRATE CONFORMATION; DISACCHARIDES; INDICATORS AND REAGENTS; INOSITOL PHOSPHATES; LIPOPOLYSACCHARIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MYCOBACTERIUM SMEGMATIS;

EID: 0041937336     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(99)00078-6     Document Type: Article

References (41)

1. Chatterjee D., Khoo K.-H. Glycobiology. 8:1998;113-120.
2. Roach T.I.A., Barton C.H., Chatterjee D., Blackwell J.M. J. Immunol. 150:1993;1886-1896.
3. Venisse A., Fournié J.-J., Puzo G. Eur. J. Biochem. 231:1995;440-447.
4. Prinzis S., Chatterjee D., Brennan P.J. J. Gen. Microbiol. 139:1993;2649-2658.
5. Gilleron M., Himoudi N., Adam O., Constant P., Venisse A., Rivière M., Puzo G. J. Biol. Chem. 272:1997;117-124.
6. Ito Y., Ogawa T. Angew. Chem., Int. Ed. Engl. 33:1994;1765-1767.
7. Dan A., Ito Y., Ogawa T. J. Org. Chem. 60:1995;4680-4681.
8. H.B. Mereyala, S. Hotha, M.K. Gurjar, Chem. Commun. (Cambridge), (1998) 685-686.
9. Wolucka B.A., McNeil M.R., de Hoffmann E., Chojnacki T., Brennan P.J. J. Biol. Chem. 269:1994;23328-23335.
10. Lee R.E., Mikušová K., Brennan P.J., Besra G.S. J. Am. Chem. Soc. 115:1995;11829-11832.
11. Lee R.E., Brennan P.J., Besra G.S. Glycobiology. 7:1997;1121-1128.
12. Barresi F., Hindsgaul O. J. Am. Chem. Soc. 113:1991;9376-9377.
13. F. Barresi, O. Hindsgaul, Synlett, (1992) 759-761.
14. Stork G., Kim G. J. Am. Chem. Soc. 114:1992;1087-1088.
15. M. Bols, J. Chem. Soc., Chem. Commun., (1992) 913-914.
16. Bols M. Tetrahedron. 44:1993;10049-10060.
17. Krog-Jensen C., Oscarson S. J. Org. Chem. 61:1996;4512-4513.
18. Krog-Jensen C., Oscarson S. J. Org. Chem. 63:1998;1780-1784.
19. Ness R.K., Fletcher H.G. Jr. J. Am. Chem. Soc. 80:1958;2007-2010.
20. W.T. Markiewicz, J. Chem. Res. (S), (1979) 24-25.
21. S. Czernecki, T. Le Diguarher, Synthesis, (1991) 683-686.
22. Kaneko S., Kawabata Y., Ishii T., Gama Y., Kusakabe I. Carbohydr. Res. 268:1995;307-311.
23. Garegg P., Kvarnström I., Niklasson A., Niklasson G., Svensson S.C.T. J. Carbohydr. Chem. 12:1993;933-954.
24. Kornblum N., Smiley R.A., Blackwood R.K., Iffland D.C. J. Am. Chem. Soc. 77:1955;6269-6280.
25. Sproat B.S., Beijer B., Iribarren A. Nucleic Acids Res. 18:1990;41-49.
26. Gotfredsen C.H., Jacobsen J.P., Wengel J. Tetrahedron Lett. 35:1994;6941-6944.
27. Grøtli M., Douglas M., Beijer B., Eritja R., Sproat B. Biorg. Med. Chem. Lett. 7:1997;425-428.
28. Lemieux R.U., Morgan A.R. Can. J. Chem. 43:1965;2190-2198.
29. Veeneman G.H., Van Leeuwen S.H., Zuurmond H., van Boom J.H. J. Carbohydr. Chem. 9:1990;783-796.
30. Smid P., de Ruiter G.A., van der Marel G.A., Rombouts F.M., van Boom J.H. J. Carbohydr. Chem. 10:1991;833-849.
31. Gorin P.A.J., Mazurek M. Can. J. Chem. 53:1975;1212-1223.
32. Ritchie R.G.S., Cyr N., Korsch B., Koch H.J., Perlin A.S. Can. J. Chem. 53:1975;1424-1433.
33. Beier R.C., Mundy B.P. J. Carbohydr. Chem. 3:1984;253-266.
34. Serianni A.S., Barker R. J. Org. Chem. 49:1984;3292-3300.
35. Bishop C.T., Cooper F.P. Can. J. Chem. 41:1963;2743-2758.
36. Hennen W.J., Sweers H.M., Wang Y.-F., Wong C.-H. J. Org. Chem. 53:1988;4939-4945.
37. C.E. Dreef, M. Douwes, C.J.J. Elie, G.A. van der Marel, J.H. van Boom, Synthesis, (1991) 443-447.
38. Pratt C., Liu Y., Chu T., Melkonian K., Tropp B.E., Engel R. Can. J. Chem. 70:1992;2135-2141.
39. Garegg P.J., Regberg T., Stawiñski J., Strömberg R. Chem. Scr. 25:1985;280-282.
40. Garegg P.J., Lindh I., Regberg T., Stawiñski J., Henrichson C. Tetrahedron Lett. 27:1986;4055-4058.
41. Lindh I., Stawiñski J. J. Org. Chem. 54:1989;1338-1342.