Premium
Amination of ω‐Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation–Transamination Cascade
Author(s) -
Pickl Mathias,
Fuchs Michael,
Glueck Silvia M.,
Faber Kurt
Publication year - 2015
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.201500589
Subject(s) - chemistry , amination , biocatalysis , reductive amination , substrate (aquarium) , organic chemistry , aldehyde , yield (engineering) , alcohol , amine gas treating , cascade reaction , primary (astronomy) , combinatorial chemistry , catalysis , reaction mechanism , oceanography , materials science , physics , astronomy , metallurgy , geology
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 from Aspergillus fumigatus (LCAO_Af) with a ω‐transaminase from Chromobacterium 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, O 2 pressure, substrate concentration, decomposition of H 2 O 2 (derived from alcohol oxidation), NADH regeneration, and biocatalyst ratio. The substrate scope of this concept was investigated under optimized conditions by using terminally functionalized C 4 –C 11 fatty primary alcohols bearing halogen, alkyne, amino, hydroxy, thiol, and nitrile groups.