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Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects
Alternative Title具有免疫抑制活性的杠柳孕甾苷Periploside A的全合成
Zhang XH(张夏衡)1; ZHOU YU1; Zuo JP(左建平)1; Yu B(俞飚)1
2015
Source PublicationNat. Commun.
Volume6Pages:5879
AbstractPeriploside 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.
Subtype论文
Subject Area生命有机化学
DOI10.1038/ncomms6879
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000348702400003
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39481
Collection生命有机化学国家重点实验室
Corresponding AuthorYu B(俞飚)
Affiliation1.中科院上海有机化学研究所, 生命有机化学国家重点实验室
2.中科院上海药物研究所
Recommended Citation
GB/T 7714
Zhang XH,ZHOU YU,Zuo JP,et al. Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects[J]. Nat. Commun.,2015,6:5879.
APA 张夏衡,ZHOU YU,左建平,&俞飚.(2015).Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects.Nat. Commun.,6,5879.
MLA 张夏衡,et al."Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects".Nat. Commun. 6(2015):5879.
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