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Synthesis of the Trisaccharide and Tetrasaccharide Moieties of the Potent Immunoadjuvant QS‐21
Author(s) -
Zhu Xiangming,
Yu Biao,
Hui Yongzheng,
Schmidt Richard R.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300580
Subject(s) - chemistry , tetrasaccharide , trisaccharide , immunoadjuvant , stereochemistry , glucuronic acid , glycosylation , organic chemistry , polysaccharide , biochemistry , immune system , immunology , biology
The title trisaccharide and tetrasaccharide moieties have been synthesized as part of our research programme to construct the complex triterpenoid saponin QS‐21, a potent immunoadjuvant, which has been used in a series of clinical immunization trials. In view of the unwillingness of glucuronic acid as glycosyl acceptor, the branched glucuronic acid‐containing trisaccharide 20 was synthesized from D ‐glucose, which was in turn glycosylated at positions 2 and 3, followed by oxidation at position 6, in a linear sequence of 15 steps and in good overall yield. The apiose‐containing tetrasaccharide 36 was constructed by a linear glycosylation strategy from the non‐reducing terminal sugar, D ‐apiose, which was prepared from D ‐xylose by a known procedure, also in a linear sequence of 15 steps. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)