Synthesis of a heptasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype C
文献类型：期刊论文
| 作者 | Zhao, W; Kong, FZ |
| 刊名 | CARBOHYDRATE RESEARCH
 |
| 出版日期 | 2005 |
| 卷号 | 340期号:10页码:1673-1681 |
| 关键词 | Mannose Xylose Glucuronic Acid |
| DOI | 10.1016/j.carres.2005.05.003 |
| 英文摘要 | beta-D-Xylp-(1 -> 2)-alpha-D-Manp-(1 -> 3)-[beta-D-Xylp-(1 -> 2)][beta-D-Xylp-(1 -> 4)]-alpha-D-ManP)-(1 -> 3)-[beta-D-Xylp-(1 -> 4)]-alpha-D-Manp, the fragment of the exopolysaccharide from Cryptococcus neoformans serovar C, was synthesized as its methyl glycoside. Thus, chloro-acetylation of allyl 3 - O-acetyl-4,6- O-benzylidene-alpha-D-mannopyranoside (1) followed by debenzylidenation and selective 6-O-benzoylation afforded allyl 2-O-chloroacetyl-3-O-acetyl-6-O-benzoyl-alpha-D-mannopyranoside (4). Glycosylation of 4 with 2,3,4-tri-O-benzoyl-D-xylopyranosyl trichloroacetimidate (5) furnished the beta(1 -> 4)-linked disaccharide 6. Dechloroacetylation gave the disaccharide acceptor 7 and subsequent coupling with 5 produced the trisaccharide 8. Deacetylation of 8 gave the trisaccharide acceptor 9 and subsequent coupling with a disaccharide 10 produced the pentasaccharide 11. Reiteration of deallylation and trichloroacetimidate formation from 11 yielded the pentasaccharide donor 12. Coupling of a disaccharide acceptor 13 with 12 afforded the heptasaccharide 14. Subsequent deprotection gave the heptaoside 16, while selective 2-O-deacetylation of 14 gave the heptasaccharide acceptor 15. Condensation of 15 with glucopyranosyluronate imidate 17 did not yield the expected octaoside, instead, an orthoester product 18 was obtained. Rearrangement of 18 did not give the target octaoside; but produced 15. Meanwhile, there was no reaction between 15 and the glycosyl bromide donor 19. (c) 2005 Elsevier Ltd. All rights reserved. |
| 学科主题 | Biochemistry & Molecular Biology ; Chemistry |
| WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
| WOS记录号 | WOS:000230329700001 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/23377]  |
| 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 | Zhao, W,Kong, FZ. Synthesis of a heptasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype C[J]. CARBOHYDRATE RESEARCH,2005,340(10):1673-1681. |
| APA | Zhao, W,&Kong, FZ.(2005).Synthesis of a heptasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype C.CARBOHYDRATE RESEARCH,340(10),1673-1681. |
| MLA | Zhao, W,et al."Synthesis of a heptasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype C".CARBOHYDRATE RESEARCH 340.10(2005):1673-1681. |
入库方式： OAI收割
来源：生态环境研究中心
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