Abstract
The trisaccharide segment of the phenolic glycolipid I of Mycobacterium leprae was synthesized effectively in the form of β-(2-methoxycarbonylethyl)phenyl glycoside by the condensation of β-(2-methoxycarbonylethyl)phenyl 4–0-benzyl-3–0-methyl-α-l-rhamnopyranoside and 2,3-di-O-methyl-4–0-(2,4-di-0-acetyl-3,6-di-0-methyl-/?-d-glucopyranosyl)-α-l-rhamnopyrano-syl chloride in the presence of silver tritiate and 1,1,3,3-tetra-iV-methylurea, and subsequent selective deprotection. This was then coupled to BSA by the acyl azide method, giving NT-P-BSA. The NT-P-BSA showed very high reactivity and specificity to leprosy sera. The trisaccharide-BSA conjugate with a ^-linked rhamnosylrhamnose unit (/TT-P-BSA) was also synthesized.
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