Acceptor-Reactivity-Controlled Stereoconvergent Synthesis and Immunological Activity of a Unique Pentasaccharide from the Cell Wall Polysaccharide of Cutibacterium acnes C7
文献类型：期刊论文
| 作者 | Hao, Tianhui3,4; Feng, Ke2; Jin, Hongzhen1; Li, Jiawei4; Zhou, Chenkai4; Liu, Xingbang4; Zhao, Wei2; Yu, Fan1; Li, Tiehai3,4 |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2024-05-31 |
| 页码 | 9 |
| 关键词 | carbohydrates oligosaccharide synthesis stereoselective glycosylation synthesis design immunological activity |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.202405297 |
| 通讯作者 | Yu, Fan(yufan@uor.edu.cn) ; Li, Tiehai(tiehaili@simm.ac.cn) |
| 英文摘要 | Bacterial cell-surface polysaccharides are involved in various biological processes and have attracted widespread attention as potential targets for developing carbohydrate-based drugs. However, the accessibility to structurally well-defined polysaccharide or related active oligosaccharide domains remains challenging. Herein, we describe an efficiently stereocontrolled approach for the first total synthesis of a unique pentasaccharide repeating unit containing four difficult-to-construct 1,2-cis-glycosidic linkages from the cell wall polysaccharide of Cutibacterium acnes C7. The features of our approach include: 1) acceptor-reactivity-controlled glycosylation to stereoselectively construct two challenging rare 1,2-cis-ManA2,3(NAc)(2) (beta-2,3-diacetamido-2,3-dideoxymannuronic acid) linkages, 2) combination use of 6-O-tert-butyldiphenylsilyl (6-O-TBDPS)-mediated steric shielding effect and ether solvent effect to stereoselectively install a 1,2-cis-glucosidic linkage, 3) bulky 4,6-di-O-tert-butylsilylene (DTBS)-directed glycosylation to stereospecifically construct a 1,2-cis-galactosidic linkage, 4) stereoconvergent [2+2+1] and one-pot chemoselective glycosylation to rapidly assemble the target pentasaccharide. Immunological activity tests suggest that the pentasaccharide can induce the production of proinflammatory cytokine TNF-alpha in a dose-dependent manner. |
| WOS关键词 | PROPIONIBACTERIUM-ACNES ; CHEMICAL-SYNTHESIS ; D-GLUCOSAMINE ; GLYCOSYLATION ; OLIGOSACCHARIDE ; ACID |
| 资助项目 | National Natural Science Foundation of China ; Shanghai Municipal Science and Technology Major Project ; Fundamental Research Funds for the Central Universities ; [22077130] ; [22377134] ; [22077068] ; [22377060] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001236043100001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/311773]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Yu, Fan; Li, Tiehai |
| 作者单位 | 1.Univ Hlth & Rehabil Sci, Qingdao Cent Hosp, Sch Hlth & Life Sci, Qingdao 266113, Peoples R China 2.Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Tianjin 300350, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 4.Chinese Acad Sci, State Key Lab Chem Biol, Carbohydrate Based Drug Res Ctr, Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Hao, Tianhui,Feng, Ke,Jin, Hongzhen,et al. Acceptor-Reactivity-Controlled Stereoconvergent Synthesis and Immunological Activity of a Unique Pentasaccharide from the Cell Wall Polysaccharide of Cutibacterium acnes C7[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024:9. |
| APA | Hao, Tianhui.,Feng, Ke.,Jin, Hongzhen.,Li, Jiawei.,Zhou, Chenkai.,...&Li, Tiehai.(2024).Acceptor-Reactivity-Controlled Stereoconvergent Synthesis and Immunological Activity of a Unique Pentasaccharide from the Cell Wall Polysaccharide of Cutibacterium acnes C7.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,9. |
| MLA | Hao, Tianhui,et al."Acceptor-Reactivity-Controlled Stereoconvergent Synthesis and Immunological Activity of a Unique Pentasaccharide from the Cell Wall Polysaccharide of Cutibacterium acnes C7".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2024):9. |
入库方式： OAI收割
来源：上海药物研究所
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