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Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin "Julibroside J(28)" from Albizia julibrissin.

Roy B, Pramanik K, Mukhopadhyay B

Medicinal and Process Chemistry Division, Central Drug Research Institute, Chattar Manzil Palace, Lucknow, 226 001, Uttar Pradesh, India.

Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J(28), isolated from Albizia julibrissin, that showed significant in vitro antitumor activity against HeLa, Bel-7402 and PC-3M-1E8 cancer cell lines is reported. The tetrasaccharide has been synthesized as its p-methoxyphenyl glycoside starting from commercially available D: -glucose, L: -rhamnose and L: -arabinose. The trisaccharide part has been synthesized from commercially available N-acetyl D: -glucosamine, D: -fucose and D: -xylose using simple protecting group manipulations. Sulfuric acid immobilized on silica has been used successfully as a Brönsted acid catalyst for the crucial glycosylation steps.

Published 8 February 2008 in Glycoconj J, 25(2): 157-66.
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