Synthesis of Mono- and Dihydroxylated Amino Acids with New $\alpha$-Ketoglutarate-Dependent Dioxygenases: Biocatalytic Oxidation of C$-$H Bonds

Damien Baud (1) , Pierre-Loïc Saaidi (1) , Adam Monfleur (1) , Marine Harari (1) , Julien Cuccaro (1) , Aurélie Fossey (1) , Marielle Besnard (1) , Adrien Debard (1) , Aline Mariage (1) , Virginie Pellouin (1) , Jean Petit (1) , Marcel Salanoubat (1) , Jean Weissenbach (1) , Véronique de Berardinis (1) , Anne Zaparucha (1)

1 UMR 8030 - Génomique métabolique

Iron(II)/$\alpha$-ketoacid-dependent oxygenases ($\alpha$KAOs) are enzymes that mainly catalyse hydroxylation reaction. By using a genomic approach combining sequence comparison and protein-domain sharing, a set of 131 $\alpha$KAO enzymes was prepared. The screening of various substrates revealed five new $\alpha$KAOs. Four $\alpha$KAOs were found to be active towards L-lysine, L-ornithine and L-arginine with total regio- and stereoselectivities and yielding the corresponding 3- or 4-hydroxyamino acids. The enzymatic cascade reaction with two stereoselective regiodivergent $\alpha$ KAOs enabled the synthesis of 3,4-dihydroxy-L- lysine.

Mots clés: amino acids; biocatalysis; dioxygenase; hydroxylation; regioselectivity

Domaines: Catalyse

Damien Baud, Pierre-Loïc Saaidi, Adam Monfleur, Marine Harari, Julien Cuccaro, et al.. Synthesis of Mono- and Dihydroxylated Amino Acids with New $\alpha$-Ketoglutarate-Dependent Dioxygenases: Biocatalytic Oxidation of C$-$H Bonds. ChemCatChem, 2014, 6, pp.3012 - 3017. ⟨10.1002/cctc.201402498⟩. ⟨cea-01591870⟩