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Derivation of Oridonin with Bioreduction‐Responsive Disulfide Bond
Author(s) -
Du Ming,
Guo Qisang,
Feng Hua,
Lu Guolin,
Huang Xiaoyu
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300761
Subject(s) - chemistry , moiety , propanoic acid , disulfide bond , glutathione , derivative (finance) , thiol , stereochemistry , combinatorial chemistry , functional group , medicinal chemistry , organic chemistry , biochemistry , financial economics , economics , enzyme , polymer
A novel oridonin derivative substituted with 3‐((2,3‐dihydroxypropyl)dithio)‐propionyl group at 14‐ O position was synthesized through a two‐step procedure: Esterification of oridonin with 3‐(2‐pyridyldithio)propanoic acid and the subsequent thiol‐disul?de exchange reaction with 3‐mercapto‐1,2‐propanediol. The bioreduction‐responsive disulfide bond in the compound leads to high leaving ability of the 14‐ O acyl moiety when treated with glutathione as monitored by reverse phase high‐performance liquid chromatography.