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Keywords:

  • aminothioesters;
  • conformational analysis;
  • S[RIGHTWARDS ARROW]N-acyl transfer

In S-acylcysteines and homocysteines, the efficacy and rate of S[RIGHTWARDS ARROW]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.