An n.m.r. and conformational analysis of the terminal trisaccharide from the serologically active glycolipid of Mycobacterium leprae in different solvents.
The 1H- and 13C-n.m.r. spectra of allyl 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 (3), a glycoside of the terminal trisaccharide found in the phenolic glycolipid I from Mycobacterium leprae, and those of the two component disaccharides, allyl 4-O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-2,3-di-O- methyl-alpha-L-rhamnopyranoside (1) and allyl 2-O-(2,3-di-O-methyl-alpha-L-rhamnopyranosyl)-3-O-methyl-alpha-L- rhamnopyranoside (2) have been assigned completely by 1D and 2D techniques. The preferred conformations, determined by chemical shift and n.O.e. studies, were different in D2O, CD3OD, and CDCl3. The preferred conformation of 3 accorded with the results of hard-sphere exo-anomeric (HSEA) calculations.
Department of Chemistry, Carlsberg Laboratory, Valby, Denmark.
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Bock
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Hvidt
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Marino-Albernas
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Verez-Bencomo
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D009166:Mycobacterium leprae / Q000032:analysis; D012997:Solvents; D014312:Trisaccharides / Q000032:analysis
D002247:Carbon Isotopes; D012997:Solvents; D014312:Trisaccharides; C065041:allyl 2-O-(4-O-(3,6-di-O-methyl-beta-glucopyranosyl)-2,3-di-O-methyl-alpha-rhamnopyranosyl)-3-O-methyl-alpha-rhamnopyranoside