Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C neoformans serotype B
文献类型：期刊论文
| 作者 | Zhao, W; Kong, FZ |
| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY
 |
| 出版日期 | 2005 |
| 卷号 | 13期号:1页码:121-130 |
| 关键词 | Mannose Xylose Glucuronic Acid Regio- And Stereo-selective Synthesis |
| DOI | 10.1016/j.bmc.2004.09.049 |
| 英文摘要 | A heptasaccharide, beta-D-Xylp-(1-->2)-alpha-D-Manp-(1-->3)-[beta-D-XylP-(1-->2)]-alpha-D-Manp-(1-->3)-[beta-D-GlcpA-(1-->2)][beta-D-Xylp-(1-->4)]-alpha-D-Manp, the repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar 13, was synthesized as its methyl glycoside. Thus 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (7) and allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-4,6-di-O-benzoyl-alpha-D-mannopyranoside (8), readily obtained from the corresponding monosaccharide derivatives via simple transformation, were coupled to give a (1-->3)-linked tetrasaccharide 9. Deallylation of 9 followed by trichloroacetimidate formation produced the tetrasaccharide donor 11. Condensation of methyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->4)-2-O-acetyl-6-O-benzoyl-alpha-D-mannopyranoside (18) with 11 followed by selective deacetylation yielded hexasaccharide acceptor 20. Coupling of 20 with methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide (21) and subsequent deprotection furnished the target heptaoside. A hexasaccharide fragment, alpha-D-Manp-(1-->3)-[beta-D-Xylp-(1-->2)]-alpha-D-Manp-(1-->3)-[beta-D-GlcpA-(1-->2)][beta-D-Xylp-(1-->4)]-alpha-D-Manp, was also similarly synthesized as its methyl glycoside. (C) 2004 Elsevier Ltd. All rights reserved. |
| 学科主题 | Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry |
| WOS研究方向 | Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry |
| WOS记录号 | WOS:000225939200011 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/23368]  |
| 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. Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C neoformans serotype B[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2005,13(1):121-130. |
| APA | Zhao, W,&Kong, FZ.(2005).Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C neoformans serotype B.BIOORGANIC & MEDICINAL CHEMISTRY,13(1),121-130. |
| MLA | Zhao, W,et al."Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C neoformans serotype B".BIOORGANIC & MEDICINAL CHEMISTRY 13.1(2005):121-130. |
入库方式： OAI收割
来源：生态环境研究中心
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