TY - JOUR
T1 - α-Substitution effects on the ease of S → N-Acyl transfer in aminothioesters
AU - El-Gendy, Bahaa El Dien M.
AU - Ghazvini Zadeh, Ebrahim H.
AU - Sotuyo, Ania C.
AU - Pillai, Girinath G.
AU - Katritzky, Alan R.
PY - 2013/5
Y1 - 2013/5
N2 - 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, NH2) substituents. Spatial distance, b(N-C), between the terminal amine and the thioester carbon is shortened by α-C(O)X (X=OH, OMe, NH2) substituents.
AB - 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, NH2) substituents. Spatial distance, b(N-C), between the terminal amine and the thioester carbon is shortened by α-C(O)X (X=OH, OMe, NH2) substituents.
KW - Aminothioesters
KW - Conformational analysis
KW - S→N-acyl transfer
UR - http://www.scopus.com/inward/record.url?scp=84876854058&partnerID=8YFLogxK
U2 - 10.1111/cbdd.12092
DO - 10.1111/cbdd.12092
M3 - Article
C2 - 23205543
AN - SCOPUS:84876854058
SN - 1747-0277
VL - 81
SP - 577
EP - 582
JO - Chemical Biology and Drug Design
JF - Chemical Biology and Drug Design
IS - 5
ER -