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• W2803207737 abstract "The stereochemistry of non-enzyme catalyzed nucleophilic addition of GSH to 4'-hydroxychalcone 1 and its bis-Mannich derivative 2 was investigated at different pH values (pH 3.2, 6.1, 7.4, and 8.0). The stereochemical outcome of the reactions was evaluated by HPLC-UV-Vis method. Under strongly acidic conditions (pH 3.2), an unexpected diastereoselective addition of GSH onto the bis-Mannich derivative 2 was observed. Such a selectivity could not be observed in the similar reaction of 2 with N-acetylcysteine. The observed stereoselectivity can be rationalized by ion-pair formation between the protonated Mannich nitrogens and the deprotonated GSH(glutamate)-carboxylate. To the best of our knowledge, this is the first example of reagent-induced asymmetric induction in Michael-type additions of thiols." @default.
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• W2803207737 date "2018-05-18" @default.
• W2803207737 modified "2023-10-04" @default.
• W2803207737 title "Reagent-induced asymmetric induction in addition reaction of reduced glutathione ontobis-Mannich chalcones" @default.
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• W2803207737 doi "https://doi.org/10.1002/ardp.201700386" @default.
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