A general method for the synthesis of oligosaccharides consisting of alpha-(1 -> 2)- and alpha-(1 -> 3)-linked rhamnan backbones and GlcNAc side chains
文献类型：期刊论文
| 作者 | Zhang, HJ; Kong, FZ |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2003 |
| 卷号 | 59期号:9页码:1429-1441 |
| 关键词 | Pseudomonas Syringae Rhamnose Glycosylation |
| DOI | 10.1016/S0040-4020(03)00075-9 |
| 英文摘要 | A general method has been developed for the synthesis of oligosaccharides consisting of (1-->2)- and (1-->3)-linked rhammans with GlcNAc side chains. As examples, highly effective and convergent syntheses of two decasaccharides in the O polysaccharide moiety of the lipopolysaccharide of the phytopathogenic bacterium Pseudomonas syringae pv. ribicola NCPPB 1010 were achieved. The two decasaccharides consist of O polysaccharide repeating units I+II and II+I, respectively. Allyl 3-0-acetyl-4-O-benzoyl-alpha-L-rhanmopyranoside, allyl 2-O-benzoyl-3-O-chloroacetyl-alpha-L-rhamnopyranoside, 2,4-di-O-benzoyl-3-O-chloroacetyl-(alpha-L-rhamnopyranosyl trichloroacetimidate, and 3-O-acetyl-2,4-di-O-benzoyl-alpha-L-rhanmopyranosyl trichloroacetimidate, which were obtained by highly regioselective 3-O-acylations, were used as the key synthons to obtain the required alpha-(1-->2)- and a-(1-->3)-linked rhamnoocta. saccharide acceptors with 3(3)- and 3(7)-free hydroxyl groups. Therefore, several disaccharides were synthesized, from which tetrasaccharides and hexasaccharides were then synthesized. Coupling of the hexasaccharide donors with the disaccharide acceptors gave the octasaccharide acceptors. Finally, the coupling of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with the octasaccharide acceptors, followed by deprotection, afforded the two target decasaccharides. A repeating hexasaccharide unit of the cell wall polysaccharide of beta-hemolytic Streptococci Group A was also synthesized in a similar way. (C) 2003 Elsevier Science Ltd. All rights reserved. |
| WOS研究方向 | Chemistry |
| WOS记录号 | WOS:000181219100008 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/23808]  |
| 专题 | 生态环境研究中心_中国科学院环境生物技术重点实验室 |
| 推荐引用方式 GB/T 7714 | Zhang, HJ,Kong, FZ. A general method for the synthesis of oligosaccharides consisting of alpha-(1 -> 2)- and alpha-(1 -> 3)-linked rhamnan backbones and GlcNAc side chains[J]. TETRAHEDRON,2003,59(9):1429-1441. |
| APA | Zhang, HJ,&Kong, FZ.(2003).A general method for the synthesis of oligosaccharides consisting of alpha-(1 -> 2)- and alpha-(1 -> 3)-linked rhamnan backbones and GlcNAc side chains.TETRAHEDRON,59(9),1429-1441. |
| MLA | Zhang, HJ,et al."A general method for the synthesis of oligosaccharides consisting of alpha-(1 -> 2)- and alpha-(1 -> 3)-linked rhamnan backbones and GlcNAc side chains".TETRAHEDRON 59.9(2003):1429-1441. |
入库方式： OAI收割
来源：生态环境研究中心
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。