The Allyl Group for Protection in Carbohydrate Chemistry. Part 19. The Coupling of Allyl 2,3-Di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside to Bovine Serum Albumin. Preparation of a Diagnostic Reagent for Antibodies to the Major Glycolipid of Mycobacterium...

Article abstract of DOI:10.1039/P19870001165

Epoxidation of allyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside and subsequent alkaline hydrolysis of the epoxide and hydrogenolysis of the benzyl groups gave 2',3'-dihydroxypropyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside which was cleaved with sodium metaperiodate to give the corresponding formylmethyl glycoside.Two other routes to the latter compound, via allyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside, were also developed.The formylmethyl glycoside was coupled to bovine serum albumin using 'reductive amination' in the presence of sodium cyanoborohydride to give a glycoconjugate useful for the serodiagnosis of antibodies to the major glycolipid of Mycobacterium leprae in the sera of leprosy patients. 5',6'-Dihydroxyhexyl and 10',11'-dihydroxyundecyl 3,6-di-O-methyl-β-D-glucopyranosides were also prepared as intermediates for the synthesis of the 4-formylbutyl and 9-formylnonyl glucosides respectively which are also suitable for coupling to bovine serum albumin by the 'reductive amination' technique.

Full text of DOI:10.1039/P19870001165

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