Journal
CHEMICAL BIOLOGY & DRUG DESIGN
Volume 81, Issue 5, Pages 577-582Publisher
WILEY-BLACKWELL
DOI: 10.1111/cbdd.12092
Keywords
aminothioesters; conformational analysis; S -> N-acyl transfer
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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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