Conformation-Controlled Hydrogen-Bond-Mediated Aglycone Delivery Method for alpha-Xylosylation
文献类型：期刊论文
| 作者 | Cai, Deqin1,3; Bian, Ya2,3; Wu, Shengjie1,3; Ding, Kan1,3
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2021-08-06 |
| 卷号 | 86期号:15页码:9945-9960 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.1c00187 |
| 通讯作者 | Ding, Kan(dingkan@simm.ac.cn) |
| 英文摘要 | alpha-Xylosylated glycans and xylosyl derivatives are biomedically important molecules which show numerous bioactivities against infection, cancer, inflammation, and so on. Lacking an efficient alpha-xylosylation method, the synthesis of a-xyloside-containing molecules was full of challenges. Herein, a robust method is presented for selective alpha-xylosylation via combination of a rare conformation-controlled strategy and the hydrogen-bond-mediated aglycone delivery method. Various native branched alpha-xyloside structures necessitate an orthogonally protected xyloside, and a three-pot preparation method of the xylosyl donor was developed for this novel alpha-xylosylation method, which was further applied in the first synthesis of the side chain N of xyloglucan. This work provides an efficient alpha-xylosylation method which would make various alpha-xyloside structures achievable. The conformation-controlled strategy also has important reference to the chemistry of five-carbon pyranose. |
| WOS关键词 | SULFATED GLYCOSYL SERINES ; STEREOSELECTIVE GLYCOSYLATION ; XYLOGLUCO-OLIGOSACCHARIDES ; CHEMICAL-SYNTHESIS ; HEPARAN-SULFATE ; CELL-WALLS ; FACTOR-VII ; GLYCOSAMINOGLYCAN ; DERIVATIVES ; GROWTH |
| 资助项目 | Key New Drug Creation and Manufacturing Program[2019ZX09735001] ; National Key R&D Program of China[2019YFC1711000] ; Ministry of Science and Technology |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000684025500003 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/298094]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Ding, Kan |
| 作者单位 | 1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Shanghai Univ Tradit Chinese Med, Interdisciplinary Sci Res Inst, Shanghai 201203, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, Glycochem & Glycobiol Lab, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Cai, Deqin,Bian, Ya,Wu, Shengjie,et al. Conformation-Controlled Hydrogen-Bond-Mediated Aglycone Delivery Method for alpha-Xylosylation[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(15):9945-9960. |
| APA | Cai, Deqin,Bian, Ya,Wu, Shengjie,&Ding, Kan.(2021).Conformation-Controlled Hydrogen-Bond-Mediated Aglycone Delivery Method for alpha-Xylosylation.JOURNAL OF ORGANIC CHEMISTRY,86(15),9945-9960. |
| MLA | Cai, Deqin,et al."Conformation-Controlled Hydrogen-Bond-Mediated Aglycone Delivery Method for alpha-Xylosylation".JOURNAL OF ORGANIC CHEMISTRY 86.15(2021):9945-9960. |
入库方式： OAI收割
来源：上海药物研究所
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