Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects

Xiaheng Zhang, Yu Zhou, Jianping Zuo and Biao Yu ()
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Xiaheng Zhang: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
Yu Zhou: State Key Laboratory of New Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Jianping Zuo: State Key Laboratory of New Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Biao Yu: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Nature Communications, 2015, vol. 6, issue 1, 1-10

Abstract: Abstract 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 Sinaÿ’s and Crich’s protocol for the formation of orthoester and acetal glycosides, respectively. The 2-deoxy-β-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.

Date: 2015
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DOI: 10.1038/ncomms6879

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