Biocatalytic Recycling Cascades Combining Aldolases and Transaminases for the Stereo‐Controlled Synthesis of γ‐Hydroxy‐α‐Amino Acids

Author:

Gourbeyre Léa1,Perrard Jules1,Bouzid Stephany1,Matéos Alexandre1,Hélaine Virgil1ORCID,Guérard‐Hélaine Christine1,Lemaire Marielle1,Petit Jean‐Louis2,de Berardinis Véronique2,Gefflaut Thierry1ORCID

Affiliation:

1. Université Clermont Auvergne Clermont-Auvergne INP, CNRS Institut de Chimie de Clermont-Ferrand F-63000 Clermont-Ferrand France

2. Génomique métabolique Genoscope Institut François Jacob CEA CNRS, Univ Evry, Univ Paris-Saclay 91057 Evry France

Abstract

AbstractRecycling cascades combining aldolases and transaminases from biodiversity were designed for the stereoselective synthesis of various isomers of γ‐hydroxy‐α‐amino acids. Aldolases with opposite enantioselectivities were combined with a d‐α‐transaminase to prepare in a single step, dsyn or danti‐4‐hydroxyglutamic acid with high yield and stereoselectivity. Bioactive (2S,3R,4S)‐4‐hydroxy‐isoleucine was also efficiently prepared via an aldolase‐transaminase recycling cascade. In that case, the unexpected high stereoselectivity was shown to result from the thermodynamically‐driven formation of a stable derivative of the product. This novel approach was applied to the synthesis of lsyn and dsyn‐4‐hydroxynorvaline as well as for 3 new β‐branched‐γ‐hydroxy‐α‐amino acids, analogues of 4‐hydroxyisoleucine.

Publisher

Wiley

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