Stereoselective synthesis of γ-hydroxy-α-amino acids through aldolase–transaminase recycling cascades

Christine Guérard-Hélaine; Egon Heuson; Moussa Ndiaye; Léa Gourbeyre; Marielle Lemaire; Virgil Hélaine; Franck Charmantray; Jean-Louis Petit; Marcel Salanoubat; Véronique de Berardinis; Thierry Gefflaut

doi:10.1039/C7CC00742F

Stereoselective synthesis of γ-hydroxy-α-amino acids through aldolase–transaminase recycling cascades†

Christine Guérard-Hélaine,^a Egon Heuson,^a Moussa Ndiaye,^a Léa Gourbeyre,^a Marielle Lemaire,^a Virgil Hélaine,^a Franck Charmantray,^a Jean-Louis Petit,^b Marcel Salanoubat,^b Véronique de Berardinis^b and Thierry Gefflaut

*^a

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^a Université Clermont Auvergne, CNRS, SIGMA Clermont, Institut de Chimie de Clermont-Ferrand, F-63000 Clermont-Ferrand, France
E-mail: thierry.gefflaut@uca.fr

^b CEA, DRF, IBFJ, Genoscope, CNRS, Université d’Evry Val d’Essonne, UMR 8030, 91057 Evry, France

Abstract

Efficient bi-enzymatic cascades combining aldolases and α-transaminases were designed for the synthesis of γ-hydroxy-α-amino acids. These recycling cascades provide high stereoselectivity, atom economy, and an equilibrium shift of the transamination. L-syn or anti-4-hydroxyglutamic acid and D-anti-4,5-dihydroxynorvaline were thus prepared in 83–95% yield in one step from simple substrates.

Chemical Communications

Stereoselective synthesis of γ-hydroxy-α-amino acids through aldolase–transaminase recycling cascades†

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Stereoselective synthesis of γ-hydroxy-α-amino acids through aldolase–transaminase recycling cascades

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