TY - JOUR
T1 - One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases
AU - Correia Cordeiro, Raquel S.
AU - Ríos-Lombardía, Nicolás
AU - Morís, Francisco
AU - Kourist, Robert
AU - González-Sabín, Javier
PY - 2019/2/20
Y1 - 2019/2/20
N2 - An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω-transaminase, ω-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor®, a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.
AB - An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω-transaminase, ω-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor®, a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.
KW - alcohol dehydrogenase
KW - enzymatic cascade
KW - one-pot reaction
KW - oxime
KW - transaminase
UR - http://www.scopus.com/inward/record.url?scp=85060182824&partnerID=8YFLogxK
U2 - 10.1002/cctc.201801900
DO - 10.1002/cctc.201801900
M3 - Article
AN - SCOPUS:85060182824
SN - 1867-3880
VL - 11
SP - 1272
EP - 1277
JO - ChemCatChem
JF - ChemCatChem
IS - 4
ER -