Synthesis of β(1,3) oligoglucans exhibiting a Dectin-1 binding affinity and their biological evaluation
Synthesis of β(1,3) oligoglucans exhibiting a Dectin-1 binding affinity and their biological evaluation
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DOI：
10.1016/j.bmc.2012.04.017
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发表时间：
2012-06-15
影响因子：
3.5
通讯作者：
Takahashi, Takashi
中科院分区：
文献类型：
--
作者：
Tanaka, Hiroshi;Kawai, Tetsuya;Takahashi, Takashi
In this report, we describe the synthesis and biological evaluation of beta(1,3) oligosaccharides that contain an aminoalkyl group and their biological evaluation. A 2,3 diol glycoside with a 4,6 benzylidene protecting group was used as an effective glycosyl acceptor for the synthesis of some beta(1,3) linked glycosides. The use of a combination of a linear tetrasaccharide and a branched pentasaccharide as glycosyl donors led to the preparation of beta(1,3) linear octa-to hexadecasaccharides and branched nona-to heptadecasaccharides in good total yields. Measurements of the competitive effects of the oligosaccharides on the binding of a soluble form of Dectin-1 to a solid-supported Schizophyllan (SPG) revealed that the branched heptadecasaccharide and the linear hexadecasaccharides also have binding activity for Dectin-1. In addition, the two oligosaccharides, both of which contain a beta(1,3) hexadecasaccharide backbone, exhibited agonist activity in a luciferase-assisted NF-kappa B assay. STD-NMR analyses of complexes of Dectin-1 and the linear hexadecasaccharides clearly indicate Dectin-1 specifically recognizes the sugar part of the oligosaccharides and not the aminoalkyl chain. (C) 2012 Published by Elsevier Ltd.
