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α‐Substitution Effects on the Ease of S → N ‐Acyl Transfer in Aminothioesters
Author(s) -
ElGendy Bahaa ElDien M.,
Ghazvini Zadeh Ebrahim H.,
Sotuyo Ania C.,
Pillai Girinath G.,
Katritzky Alan R.
Publication year - 2013
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12092
Subject(s) - thioester , chemistry , quantum chemical , amine gas treating , stereochemistry , acyl group , acylation , group (periodic table) , molecule , organic chemistry , enzyme , catalysis
In S ‐acylcysteines and homocysteines, the efficacy and rate of S → N ‐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 α‐C(O)X (X = OH, OMe, NH 2 ) substituents.