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

Maité Sylla-Iyarreta Veitía (1, 2) , Annie Falguieres (1, 2) , Clotilde Ferroud (1, 2) , Pierre Jorda (1, 2) , Pierre Louis Brun (1, 2)

1 LTCP - Laboratoire de transformations chimiques et pharmaceutiques
2 CNAM - Conservatoire National des Arts et Métiers [CNAM]

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.

Domaines: Chimie organique

Maité Sylla-Iyarreta Veitía, Annie Falguieres, Clotilde Ferroud, Pierre Jorda, Pierre Louis Brun. Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step. Tetrahedron: Asymmetry, 2009, 20 (18), pp.2077-2089. ⟨10.1016/j.tetasy.2009.07.045⟩. ⟨hal-01487420⟩