Synthesis of beta-D-Glcp-(1 -> 2)-[beta-D-Ribf-(1 -> 3)-]alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-alpha-L-Rhap, the repeating unit of the lipopolysaccharide of Acetobacter diazotrophicus PAL 5
文献类型：期刊论文
| 作者 | Zhang, JJ; Kong, FZ |
| 刊名 | JOURNAL OF CARBOHYDRATE CHEMISTRY
 |
| 出版日期 | 2002 |
| 卷号 | 21期号:6页码:579-589 |
| 关键词 | Regio- And Stereoselective Synthesis Rhamnan Trichloroacetimidate |
| DOI | 10.1081/CAR-120016856 |
| 英文摘要 | A pentasaccharide, the major repeating unit of the lipopolysaccharide (LPS) of the nitrogen fixing bacterium Acetobacter diazotrophicus PAL 5 was efficiently synthesized as its allyl glycoside using a regio- and stereoselective strategy. The key acceptor, allyl 3-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranoside (3), was prepared by selective 3-O-acetylation of allyl 4-O-benzoyl-alpha-L-rhamnopyranoside. Condensation of 3 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate furnished the disaccharide 5. Deallylation and subsequent trichloroacetimidation of 5 afforded 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 2)-3-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (10). Selective 3-O-glycosylation of allyl alpha-L-rhamnopyranoside (1) with 10 followed by benzoylation gave trisaccharide (12), which could be conveniently converted to a donor (14). Condensation of 14 with allyl 3,4-di-O-benzoyl-alpha-L-rhamnopyranoside (15) gave tetrasaccharide, 16. Selective deacetylation of 16 gave the acceptor 17 which was ribosylated to furnish the protected pentasaccharide, and finally deprotection led to the title compound. |
| WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
| WOS记录号 | WOS:000180055900011 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/23973]  |
| 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, JJ,Kong, FZ. Synthesis of beta-D-Glcp-(1 -> 2)-[beta-D-Ribf-(1 -> 3)-]alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-alpha-L-Rhap, the repeating unit of the lipopolysaccharide of Acetobacter diazotrophicus PAL 5[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY,2002,21(6):579-589. |
| APA | Zhang, JJ,&Kong, FZ.(2002).Synthesis of beta-D-Glcp-(1 -> 2)-[beta-D-Ribf-(1 -> 3)-]alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-alpha-L-Rhap, the repeating unit of the lipopolysaccharide of Acetobacter diazotrophicus PAL 5.JOURNAL OF CARBOHYDRATE CHEMISTRY,21(6),579-589. |
| MLA | Zhang, JJ,et al."Synthesis of beta-D-Glcp-(1 -> 2)-[beta-D-Ribf-(1 -> 3)-]alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-alpha-L-Rhap, the repeating unit of the lipopolysaccharide of Acetobacter diazotrophicus PAL 5".JOURNAL OF CARBOHYDRATE CHEMISTRY 21.6(2002):579-589. |
入库方式： OAI收割
来源：生态环境研究中心
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