简化寡糖合成：乳糖胺和唾液酸化乳糖胺寡糖供体的高效合成

Simplifying oligosaccharide synthesis: efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors.

作者信息

Yan Fengyang, Mehta Seema, Eichler Eva, Wakarchuk Warren W, Gilbert Michel, Schur Melissa J, Whitfield Dennis M

机构信息

Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Room 3024, Ottawa, Ontario, K1A 0R6, Canada.

出版信息

J Org Chem. 2003 Mar 21;68(6):2426-31. doi: 10.1021/jo026569v.

DOI:10.1021/jo026569v

PMID:12636412

Abstract

A practical sequence is described for converting d-glucosamine into peracetylated Gal(beta-1,4)GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

摘要

描述了一种实用的序列，该序列基于化学酶促寡糖合成的合成策略，将d-葡萄糖胺转化为全乙酰化的Gal(β-1,4)GlcNTroc(β1-S)Ph和Neu5Ac(α-2,3)Gal(β-1,4)GlcNTroc(β1-S)Ph构建块。已知的三氯乙氧基羰基（N-Troc）保护基被选为适用于酶促和化学反应条件的保护基。这些寡糖构建块被证明是有效的供体，可用于聚合物PEG连接受体的无反应性OH-3的β选择性糖基化反应，以及甘露糖受体的轴向OH-2的β选择性糖基化反应，产率良好。所得的复杂寡糖可用于疫苗和药物应用。