Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects
文献类型：期刊论文
| 作者 | Zhang, Xiaheng1; Zhou, Yu2 ; Zuo, Jianping2; Yu, Biao1
|
| 刊名 | NATURE COMMUNICATIONS
 |
| 出版日期 | 2015-01 |
| 卷号 | 6 |
| ISSN号 | 2041-1723 |
| DOI | 10.1038/ncomms6879 |
| 文献子类 | Article |
| 英文摘要 | Periploside A is a pregnane hexasaccharide identified from the Chinese medicinal plant Periploca sepium, which features a unique seven-membered formyl acetal bridged orthoester (FABO) motif and potent immunosuppressive activities. Here, we show the synthesis of this molecule in a total of 76 steps with the longest linear sequence of 29 steps and 9.2% overall yield. The FABO motif is constructed via a combination of Sinay's and Crich's protocol for the formation of orthoester and acetal glycosides, respectively. The 2-deoxy-beta-glycosidic linkages are assembled stereoselectively with judicious choice of the glycosylation methods. The epimer at the spiro-quaternary carbon in the FABO motif has also been elaborated in a stereo-controlled manner. This epimer, as well as the synthetic analogues bearing the FABO motif, retain largely the inhibitory activities of periploside A against the proliferation of T-lymphocyte, indicating the importance of the chemical connection of the FABO motif to their immunosuppressive activity. |
| WOS关键词 | CHEMICAL-CONSTITUENTS ; ANTITUMOR FRACTION ; PERIPLOCOSIDE-E ; STEREOSELECTIVE-SYNTHESIS ; GLYCOSYL DONORS ; SEPIUM ; THIOGLYCOSIDES ; 2-DEOXY-BETA-GLYCOSIDES ; ALKYNYLBENZOATES ; GLYCOSIDATION |
| 资助项目 | National Natural Science Foundation of China[21432012] ; National Natural Science Foundation of China[91213301] ; Ministry of Sciences and Technology of China[2012ZX09502-002] ; E-Institute of Shanghai Municipal Education Commission[E09013] |
| WOS研究方向 | Science & Technology - Other Topics |
| 语种 | 英语 |
| WOS记录号 | WOS:000348702400003 |
| 出版者 | NATURE PUBLISHING GROUP |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276765]  |
| 专题 | 药理学第一研究室 药物化学研究室 |
| 通讯作者 | Yu, Biao |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab New Drug Res, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhang, Xiaheng,Zhou, Yu,Zuo, Jianping,et al. Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects[J]. NATURE COMMUNICATIONS,2015,6. |
| APA | Zhang, Xiaheng,Zhou, Yu,Zuo, Jianping,&Yu, Biao.(2015).Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects.NATURE COMMUNICATIONS,6. |
| MLA | Zhang, Xiaheng,et al."Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects".NATURE COMMUNICATIONS 6(2015). |
入库方式： OAI收割
来源：上海药物研究所
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