Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step

Article abstract of DOI:10.1016/j.tetasy.2009.07.045

Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β³-amino nitriles into their corresponding N-protected β³-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β³-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β³-amino nitriles. Two simple and efficient procedures to prepare the β³-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.