title: Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation-Transamination Cascade.
abstract: Amination of non-activated aliphatic fatty alcohols to the corresponding primary amines was achieved through a five-enzyme cascade reaction by coupling a long-chain alcohol oxidase fromAspergillus fumigatus(LCAO_Af) with a ω-transaminase fromChromobacterium violaceum(ω-TA_Cv). The alcohol was oxidized at the expense of molecular oxygen to yield the corresponding aldehyde, which was subsequently aminated by the PLP-dependent ω-TA to yield the final primary amine product. The overall cascade was optimized with respect to pH, O2pressure, substrate concentration, decomposition of H2O2(derived from alcohol oxidation), NADH regeneration, and biocatalyst ratio. The substrate scope of this concept was investigated under optimized conditions by using terminally functionalized C4-C11fatty primary alcohols bearing halogen, alkyne, amino, hydroxy, thiol, and nitrile groups.
authors.affiliation: Department of Chemistry, Organic&Bioorganic Chemistry, University of Graz Heinrichstrasse 28, 8010, Graz (Austria) E-mail: Kurt.Faber@Uni-Graz.at.
authors.forename: Mathias
authors.initials: M
authors.lastname: Pickl
authors.affiliation: Department of Chemistry, Organic&Bioorganic Chemistry, University of Graz Heinrichstrasse 28, 8010, Graz (Austria) E-mail: Kurt.Faber@Uni-Graz.at.
authors.forename: Michael
authors.initials: M
authors.lastname: Fuchs
authors.affiliation: Austrian Centre of Industrial Biotechnology (ACIB GmbH) Petersgasse 14, 8010, Graz (Austria) ; Department of Chemistry, Organic&Bioorganic Chemistry, University of Graz Heinrichstrasse 28, 8010, Graz (Austria) E-mail: Kurt.Faber@Uni-Graz.at.
authors.forename: Silvia M
authors.initials: SM
authors.lastname: Glueck
authors.affiliation: Department of Chemistry, Organic&Bioorganic Chemistry, University of Graz Heinrichstrasse 28, 8010, Graz (Austria) E-mail: Kurt.Faber@Uni-Graz.at.
authors.forename: Kurt
authors.initials: K
authors.lastname: Faber
keywords: alcohol oxidase; amination; biocatalysis; cascade; transaminase