Synthesis and NMR analysis of 13C-labeled oligosaccharides corresponding to the major glycolipid from Mycobacterium leprae.
An improved synthesis of propyl 4-O-(3,6-di-O-methyl- beta-D-glucopyranosyl)-2,3-di-O-methyl-alpha-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-2,3-di-O-methyl-alpha-L - rhamnopyranosyl]-3-O-methyl-alpha-L-rhamnopyranoside is also reported. The di- and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.
Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada.
X
X
Wu
J R
JR
Mariño-Albernas
F I
FI
Auzanneau
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V
Verez-Bencomo
B M
BM
Pinto
D000942:Antigens, Bacterial / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D004187:Disaccharides / Q000138:chemical synthesis*; D006017:Glycolipids / Q000138:chemical synthesis*; D006241:Haptens / Q000737:chemistry; D007553:Isotope Labeling; D008969:Molecular Sequence Data; D009166:Mycobacterium leprae / Q000737:chemistry* / Q000276:immunology; D019906:Nuclear Magnetic Resonance, Biomolecular; D014312:Trisaccharides / Q000138:chemical synthesis*
D000942:Antigens, Bacterial; D002247:Carbon Isotopes; D004187:Disaccharides; D006017:Glycolipids; D006241:Haptens; D014312:Trisaccharides