Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype B
文献类型：期刊论文
| 作者 | Zhao, W; Kong, FZ |
| 刊名 | CARBOHYDRATE RESEARCH
 |
| 出版日期 | 2004 |
| 卷号 | 339期号:10页码:1779-1786 |
| 关键词 | Mannose Xylose Glucuronic Acid |
| DOI | 10.1016/j.carres.2004.04.010 |
| 英文摘要 | beta-D-Xylp-(1 --> 4)-alpha-D-Manp-(1 --> 3)-[beta-D-XylP-(1 --> 2)]-alpha-D-Manp-(1 --> 3)-[beta-D-Xylp-(1 --> 2)] -alpha-D-Manp, the fragment of the exopolysaccharide from Cryptococcus neoformans serovar B, was synthesized as its methyl glycoside. Thus, acetylation of allyl 3-O-benzoyl-4,6-O-benzylidene-alpha-D-mannopyranoside (1) followed by debenzylidenation and selective 6-O-benzoylation afforded allyl 2-O-acetyl-3,6-di-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. Deallylation followed by trichloroacetimidate formation gave the disaccharide donor 8, and subsequent coupling with allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1 --> 2)-4,6-di-O-benzoyl-alpha-D-mannopyranoside (9), produced the tetrasaccharide 10. Reiteration of deallylation and trichloroacetimidate formation from 10 yielded the tetrasaccharide donor 12. The downstream disaccharide acceptor 18 was obtained by condensation of 5 with methyl 3-O-acetyl-4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenation, benzoylation, and selective 3-O-deacetylation. Coupling of 18 with 12 afforded the hexasaccharide 19, and subsequent deprotection gave the hexasaccharide glycoside 20. Selective 2"-O-deacetylation of 19 gave the hexasaccharide acceptor 21. Condensation of 21 with glucopyranosyluronate imidate 22 did not produce the expected heptasaccharide glycoside; instead, a transacetylation product 19 was obtained. Meanwhile, there was no reaction between 21 and the bromide donor 23. (C) 2004 Elsevier Ltd. All rights reserved. |
| WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
| WOS记录号 | WOS:000222746900013 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/23598]  |
| 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 hexasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype B[J]. CARBOHYDRATE RESEARCH,2004,339(10):1779-1786. |
| APA | Zhao, W,&Kong, FZ.(2004).Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype B.CARBOHYDRATE RESEARCH,339(10),1779-1786. |
| MLA | Zhao, W,et al."Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C-neoformans serotype B".CARBOHYDRATE RESEARCH 339.10(2004):1779-1786. |
入库方式： OAI收割
来源：生态环境研究中心
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