Regioselective Chemoenzymatic Synthesis of Ganglioside Disialyl Tetrasaccharide Epitopes
Author(s) -
Xin Meng,
Wenlong Yao,
Jiansong Cheng,
Xu Zhang,
Lan Jin,
Hai Yu,
Xi Chen,
Fengshan Wang,
Hongzhi Cao
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja5000609
Subject(s) - tetrasaccharide , chemistry , regioselectivity , epitope , stereochemistry , trisaccharide , diastereomer , organic chemistry , antigen , catalysis , polysaccharide , genetics , biology
A novel chemoenzymatic approach for the synthesis of disialyl tetrasaccharide epitopes found as the terminal oligosaccharides of GD1α, GT1aα, and GQ1bα is described. It relies on chemical manipulation of enzymatically generated trisaccharides as conformationally constrained acceptors for regioselective enzymatic α2-6-sialylation. This strategy provides a new route for easy access to disialyl tetrasaccharide epitopes and their derivatives.
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