Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy
文献类型：期刊论文
| 作者 | Zhang,Yunqin; Wang,Leilei; Zhou,Qingli; Li,Zuoshan; Li,Dan; Yin,Caixia; Wang,Xiufang; Xiao,Guozhi |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2023 |
| 关键词 | Anti-Inflammatory Activity Lipopolysaccharides Oligosaccharide Synthesis Orthogonal One-Pot Glycosylation Stereoselectivity STEREOSELECTIVE-SYNTHESIS CHEMICAL-SYNTHESIS ACID DONORS ALKYNYLBENZOATES GLYCOSIDES DISCOVERY CATALYSIS GLYCANS FOCUS |
| ISSN号 | 1521-3773 |
| DOI | 10.1002/anie.202301351 |
| 英文摘要 | Lipopolysaccharides from Bacteroides vulgatus represent interesting targets for the treatment of inflammatory bowel diseases. However, efficient access to long, branched and complex lipopolysaccharides remains challenging. Herein, we report the modular synthesis of a tridecasaccharide from Bacteroides vulgates through an orthogonal one-pot glycosylation strategy based on glycosyl ortho-(1-phenylvinyl)benzoates, which avoids the issues of thioglycoside-based one-pot synthesis. Our approach also features: 1) 5,7-O-di-tert-butylsilylene-directed glycosylation for stereoselective construction of the alpha-Kdo linkage; 2) hydrogen-bond-mediated aglycone delivery for the stereoselective formation of beta-mannosidic bonds; 3) remote anchimeric assistance for stereoselective assembly of the alpha-fucosyl linkage; 4) several orthogonal one-pot synthetic steps and strategic use of orthogonal protecting groups to streamline oligosaccharide assembly; 5) convergent [1+6+6] one-pot synthesis of the target. |
| 学科主题 | Chemistry |
| WOS记录号 | WOS:000955157800001 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/75551]  |
| 专题 | 中国科学院昆明植物研究所 |
| 推荐引用方式 GB/T 7714 | Zhang,Yunqin,Wang,Leilei,Zhou,Qingli,et al. Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023. |
| APA | Zhang,Yunqin.,Wang,Leilei.,Zhou,Qingli.,Li,Zuoshan.,Li,Dan.,...&Xiao,Guozhi.(2023).Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. |
| MLA | Zhang,Yunqin,et al."Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023). |
入库方式： OAI收割
来源：昆明植物研究所
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