Premium
Galactose Oxidase Variants for the Oxidation of Amino Alcohols in Enzyme Cascade Synthesis
Author(s) -
Herter Susanne,
McKenna Shane M.,
Frazer Andrew R.,
Leimkühler Silke,
Carnell Andrew J.,
Turner Nicholas J.
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.201500218
Subject(s) - chemistry , galactose oxidase , regioselectivity , aldehyde oxidase , aldehyde , aldolase a , oxidase test , xanthine oxidase , enzyme , cascade reaction , amino acid , organic chemistry , alcohol dehydrogenase , aqueous solution , alcohol oxidation , stereochemistry , biochemistry , alcohol , catalysis
The use of selected engineered galactose oxidase (GOase) variants for the oxidation of amino alcohols to aldehydes under mild conditions in aqueous systems is reported. GOase variant F 2 catalyses the regioselective oxidation of N ‐carbobenzyloxy (Cbz)‐protected 3‐amino‐1,2‐propanediol to the corresponding α‐hydroxyaldehyde which was then used in an aldolase reaction. Another variant, M 3–5 , was found to exhibit activity towards free and N ‐Cbz‐protected aliphatic and aromatic amino alcohols allowing the synthesis of lactams such as 3,4‐dihydronaphthalen‐1(2 H )‐one, 2‐pyrrolidone and valerolactam in one‐pot tandem reactions with xanthine dehydrogenase (XDH) or aldehyde oxidase (PaoABC).