Enantioselective biocatalytic formal α-amination of hexanoic acid to l-norleucine

A three-step one-pot biocatalytic cascade was designed for the enantioselective formal α-amination of hexanoic acid to l-norleucine. Regioselective hydroxylation by P450CLA peroxygenase to 2-hydroxyhexanoic acid was followed by oxidation to the ketoacid by two stereocomplementary dehydrogenases. Com...

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Veröffentlicht in:	Organic & biomolecular chemistry 2018-11, Vol.16 (43), p.8030-8033
Hauptverfasser:	Dennig, Alexander, Gandomkar, Somayyeh, Cigan, Emmanuel, Reiter, Tamara C, Haas, Thomas, Hall, Mélanie, Faber, Kurt
Format:	Artikel
Sprache:	eng
Schlagworte:	Amination Amino acids Bacteria - enzymology Biocatalysis Caproates - chemistry Cytochrome P-450 Enzyme System - metabolism Enantiomers Hexanoic acid High-performance liquid chromatography Hydroxylation Liquid chromatography Norleucine Norleucine - chemistry Oxidation Stereoisomerism Stereoselectivity Substrate Specificity
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Beschreibung
Zusammenfassung:	A three-step one-pot biocatalytic cascade was designed for the enantioselective formal α-amination of hexanoic acid to l-norleucine. Regioselective hydroxylation by P450CLA peroxygenase to 2-hydroxyhexanoic acid was followed by oxidation to the ketoacid by two stereocomplementary dehydrogenases. Combination with final stereoselective reductive amination by amino acid dehydrogenase furnished l-norleucine in >97% ee.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/c8ob02212g