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alpha-Substitution Effects on the Ease of S -> N-Acyl Transfer in Aminothioesters
Journal article   Peer reviewed

alpha-Substitution Effects on the Ease of S -> N-Acyl Transfer in Aminothioesters

Bahaa El-Dien M. El-Gendy, Ebrahim H. Ghazvini Zadeh, Ania C. Sotuyo, Girinath G. Pillai and Alan R. Katritzky
Chemical biology & drug design, Vol.81(5), pp.577-582
01/05/2013
DOI: https://doi.org/10.1111/cbdd.12092
PMID: 23205543

Abstract

Biochemistry & Molecular Biology Chemistry, Medicinal Life Sciences & Biomedicine Pharmacology & Pharmacy Science & Technology
In S-acylcysteines and homocysteines, the efficacy and rate of SN-acyl transfer (5 and 6 cyclic TSs) vary with the size of S-acyl group. Conformational and quantum chemical calculations indicate that the spatial distance, b(N-C), between the terminal amine and the thioester carbon is shortened by -C(O)X (X=OH, OMe, NH2) substituents.

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