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学科主题: 生命有机化学
题名: Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase
其他题名: 作为肝素酶底物的肝素3-4糖寡糖库的建立
作者: Xu P(徐鹏); Xu WZ(许伟长); Dai YW(代元伟); Yang Y(杨友); Yu B(俞飚)
通讯作者: 俞飚
刊名: Org. Chem. Front.
发表日期: 2014
DOI: 10.1039/c4qo00039k
卷: 1, 页:405-414
英文摘要: The glycosylation reaction for construction of the challenging α-GlcN–(1→4)-GlcA/IdoA linkages has been investigated carefully. A standard protocol was thus fixed that employed 2-azido-glucopyranosyl N-phenyl trifluoroacetimidates as donors, TMSOTf as a catalyst, toluene as a solvent, and -30 °C as the working temperature. With this protocol, a variety of mono- and disaccharide donors and acceptors were condensed reliably to provide the corresponding coupled tri- and tetrasaccharides in satisfactory yields and α-selectivity, whereas a remote protecting group or a sugar unit in either the donor or the acceptor did affect considerably the outcome. The resulting tri- and tetrasaccharides bearing orthogonal protecting groups were then converted efficiently into the corresponding heparin tri- and tetrasaccharides via a robust approach involving saponification, O-sulfation, azide reduction, N-sulfation/N-acetylation, and global debenzylation. These heparin tri- and tetrasaccharides are structurally relevant to ΔHexA(2S)–GlcN(NS,6S)–GlcA–GlcN(NS,6S), a reported substrate of heparanase, and therefore could be exploited to examine the substrate specificity of this important enzyme.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/38934
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所

Recommended Citation:
Xu P,Xu WZ,Dai YW,et al. Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase[J]. Org. Chem. Front.,2014,1:405-414.
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