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Synthesis of Mono‐ and Dihydroxylated Amino Acids with New α‐Ketoglutarate‐Dependent Dioxygenases: Biocatalytic Oxidation of CH Bonds
Author(s) -
Baud Damien,
Saaidi PierreLoïc,
Monfleur Adam,
Harari Marine,
Cuccaro Julien,
Fossey Aurélie,
Besnard Marielle,
Debard Adrien,
Mariage Aline,
Pellouin Virginie,
Petit JeanLouis,
Salanoubat Marcel,
Weissenbach Jean,
de Berardinis Véronique,
Zaparucha Anne
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402498
Subject(s) - hydroxylation , chemistry , lysine , biocatalysis , enzyme , stereoselectivity , stereochemistry , amino acid , combinatorial chemistry , biochemistry , catalysis , reaction mechanism
Iron(II)/α‐ketoacid‐dependent oxygenases (αKAOs) are enzymes that mainly catalyse hydroxylation reaction. By using a genomic approach combining sequence comparison and protein‐domain sharing, a set of 131 αKAO enzymes was prepared. The screening of various substrates revealed five new αKAOs. Four αKAOs 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 αKAOs enabled the synthesis of 3,4‐dihydroxy‐ L ‐lysine.