Efficient synthesis of a library of heparin tri- and tetrasaccharides relevant to the substrate of heparanase
文献类型：期刊论文
| 作者 | Xu P(徐鹏); Xu WZ(许伟长); Dai YW(代元伟); Yang Y(杨友); Yu B(俞飚) |
| 刊名 | Org. Chem. Front.
 |
| 出版日期 | 2014 |
| 卷号 | 1页码:405-414 |
| 其他题名 | 作为肝素酶底物的肝素3-4糖寡糖库的建立 |
| 通讯作者 | 俞飚 |
| 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. |
| 学科主题 | 生命有机化学 |
| 原文出处 | http://dx.doi.org/10.1039/c4qo00039k |
| 语种 | 英语 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/38934]  |
| 专题 | 上海有机化学研究所_生命有机化学国家重点实验室 |
| 作者单位 | 中科院上海有机化学研究所 |
| 推荐引用方式 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. |
入库方式： OAI收割
来源：上海有机化学研究所
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