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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
Xu P(徐鹏); Xu WZ(许伟长); Dai YW(代元伟); Yang Y(杨友); Yu B(俞飚)
2014
发表期刊Org. Chem. Front.
卷号1页码:405-414
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.
学科领域生命有机化学
DOI10.1039/c4qo00039k
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语种英语
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/38934
专题生命有机化学国家重点实验室
通讯作者Yu B(俞飚)
作者单位中科院上海有机化学研究所
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GB/T 7714
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.
APA 徐鹏,许伟长,代元伟,杨友,&俞飚.(2014).Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase.Org. Chem. Front.,1,405-414.
MLA 徐鹏,et al."Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase".Org. Chem. Front. 1(2014):405-414.
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