Synthesis of p-trifluoroacetamidophenyl (4,6-dideoxy-4-formamido-3-C-methyl-2-O-methyl-α-L-mannopyran osyl)-(1→3)-(2-O - methyl-α-D-rhamnopyranosyl)-(1→3)-(2-O-methyl-α-L-fucopyran osyl)-(1 →3)-(α-L-rhamnopyranosyl)-(1 →2)-6-deoxy-α-L-talopyranoside: A spacer-armed pentasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 14

Carbohydrate Research

Volumn 308, Issue 3-4, 1998, Pages 247-258

  Bajza, István ^a   Kövér, Katalin E ^b   Lipták, András ^a,b  

^a Res Grp for Carbohydr of the H   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Block synthesis; Branched chain sugar; Oligosaccharide synthesis; p Trifluoroacetamidophenyl; Spacer

Indexed keywords

BRANCHED CHAIN AMINO ACID; MYCOBACTERIUM ANTIGEN; PENTASACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; ISOMER; MYCOBACTERIUM AVIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

ANTIGENS, BACTERIAL; CARBOHYDRATE SEQUENCE; GLYCOPEPTIDES; HAPTENS; MOLECULAR SEQUENCE DATA; MYCOBACTERIUM AVIUM COMPLEX; OLIGOSACCHARIDES; PROTEOLIPIDS;

EID: 0032053011     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00074-3     Document Type: Article

References (30)

1. P.J. Brennan, Rev. Infect. Dis., 11 (1989) S420-430.
2. G.O. Aspinall, D. Chatterjee, and P.J. Brennan, Adv. Carbohydr. Chem. Biochem., 51 (1995) 169-242.
3. M. McNeil, H. Gaylord, and P.J. Brennan, Carbohydr. Res., 177 (1988) 185-198.
4. G.O. Aspinall, N.K. Khare, R.K. Sood, D. Chatterjee, B. Rivoire, and P.J. Brennan, Carbohydr. Res., 216 (1991) 357-373.
5. S.W. Hunter, T. Fujiwara, R.C. Murphy, and P.J. Brennan, J. Biol. Chem., 259 (1984) 9729-9734.
6. J. Yoshimura, K.I. Sato, and R.B. Singh, Chem. Lett., (1985) 69-70.
7. J. Yoshimura, A. Aqeel, K.I. Sato, R.B. Singh, and H. Hashimoto, Carbohydr. Res., 166 (1987) 252-256.
8. R.M. Giuliano and S. Kasperowicz, Carbohydr. Res., 183 (1988) 277-285.
9. I. Bajza and A. Lipták, Carbohydr. Res., 205 (1990) 435-439.
10. G.O. Aspinall and K. Takeo, Carbohydr. Res., 121 (1983) 61-77.
11. M.K. Gurjar and G. Viswanadham, Tetrahedron Lett., 32 (1991) 6191-6194.
12. J. Kerékgyártó, Z. Szurmai, and A. Lipták, Carbohydr. Res., 245 (1993) 65-80.
13. I. Bajza, J. Kerékgyártó, J. Hajkó, L. Szilágyi, and A. Lipták, Carbohydr. Res., 253 (1994) 111-120.
14. H.M. Zuurmond, G.H. Veeneman, G.A. van der Marel, and J.H. van Boom, Carbohydr. Res., 241 (1993) 153-164.
15. B. Flaherty, W.G. Overend, and N.R. Williams, J. Chem. Soc. C, (1966) 398-403.
16. D.R. Hicks and B. Fraser-Reid, Can. J. Chem., 53 (1975) 2017-2023.
17. V. Pozsgay, Carbohydr. Res., 69 (1979) 284-286.
18. R.F. Butterworth and S. Hanessian, Synthesis, (1971) 70-88.
19. D. Neuhaus and M. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH Publishers, Cambridge (1988).
20. A. Klemer and H. Beerman, J. Carbohydr. Chem., 2 (1983) 457-459.
21. DR. Bundle, M. Gerken, and T. Peters, Carbohydr. Res., 174 (1988) 239-251.
22. G.W.J. Fleet, M.J. Gough, and P.W. Smith, Tetrahedron Lett., 25 (1984) 1853-1856.
23. K. Miyai and R.W. Jeanloz, Carbohydr. Res., 21 (1972) 45-55.
24. R.R. Schmidt, Angew. Chem. Int. Ed. Engl., 25 (1986) 212-235.
25. S.S. Rana, J.J. Barlow, and K.L. Matta, Carbohydr. Res., 96 (1981) 79-85.
26. P.J. Garegg, T. Iversen, and S. Oscarson, Carbohydr. Res., 50 (1976) C12-C14.
27. A. Borbás and A. Lipták, Carbohydr. Res., 241 (1993) 99-116.
28. G.H. Veeneman, S.H. van Leeuwen, and J.H. van Boom, Tetrahedron Lett., 31 (1990) 275-278.
29. R.R. Ernst, G. Bodenhausen, and A. Wokaum, Principles of Nuclear Magnetic Resonance in One and Two Dimensions, Oxford University Press, Oxford (1986).
30. R. Freeman, Handbook of Nuclear Magnetic Spectroscopy, Longmans, Harlow, UK (1988).