title: α-Substitution effects on the ease of S→N-acyl transfer in aminothioesters.
abstract: 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.
authors.affiliation: Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: Bahaa El-Dien M
authors.initials: Bel-D
authors.lastname: El-Gendy
authors.forename: Ebrahim H
authors.initials: EH
authors.lastname: Ghazvini Zadeh
authors.forename: Ania C
authors.initials: AC
authors.lastname: Sotuyo
authors.forename: Girinath G
authors.initials: GG
authors.lastname: Pillai
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D006710:Homocysteine / Q000737:chemistry*
chemical_list: D006710:Homocysteine; D003545:Cysteine