ALTERNATIVE SYNTHESIS OF THE END DISACCHARIDE OF THE SPECIFIC PHENOLIC GLYCOLIPID I ANTIGEN FROM MYCOBACTERIUM LEPRAE AND OTHER PARTIALLY MODIFIED DISACCHARIDES

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A simpler, more productive variation on the previously described [Infect. Immun., 43, 245(1984)]synthesis of the haptenic non-reducing-end disaccharide of phenolic glycolipid I of Mycobacterium leprae is described. Benzyl 2,3-O-is opropylidene-4-O-(3-O-methyl-2,4-di-O-acetyl-6-O-trityl-,β-D-glucopyranosy1)-α-L-rhamnopyranoside, synthesized as described previously, was de-tritylated and de-isopropylidenated, and methylated with diazomethane/BF3-etherate to give mostly the benzyl 2,3-di-O-methyl-4-O-(2,4-di-O-acetyl-3,6-di-O-methyl-β-D-glucopyranosy1)-α-L-rhamnopyranoside, but also some benzyl 2,3-di-0-methyl-4-0-(2,6-di-0-acety1-3,4-di-0-methy1-β-D-glucopyranosy1)-α-L-rhamnopyranoside, due to acetyl migration. Likewise, benzyl 2,3-O-isopropylidene-4-0-(2,4,6-tri-0-acety1-3-0-methy1-β-D-glucopyranosyl)-α-L-rhamnopyranoside upon de-isopropylidenation and methylation yielded benzyl 2,3-di-0-methyl-4-0-(2,4,6-tri-0-acety1-3-0-methy1-β-D-g1ucopyranosy1)-α-L-rhammopyranoside. Deacetylation and hydrogenolysis of these disaccharide derivatives yielded unblocked disaccharides which are suitable precursors of neoglycoonjugates to be used in the serodiagnosis of leprosy and probing the molecular requirements for antibody binding and immunogenesity.
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