TY - JOUR
T1 - Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents
AU - Paris, Juraj
AU - Telzerow, Aline
AU - Ríos-Lombardía, Nicolás
AU - Steiner, Kerstin
AU - Schwab, Helmut
AU - Morís, Francisco
AU - Gröger, Harald
AU - González-Sabín, Javier
PY - 2019/3/4
Y1 - 2019/3/4
N2 - The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-ωTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.
AB - The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-ωTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.
KW - Amines
KW - Asymmetric synthesis
KW - Biocatalysis
KW - Deep eutectic solvents
KW - Palladium catalysis
KW - Suzuki cross-coupling reaction
UR - http://www.scopus.com/inward/record.url?scp=85061899612&partnerID=8YFLogxK
U2 - 10.1021/acssuschemeng.8b06715
DO - 10.1021/acssuschemeng.8b06715
M3 - Article
AN - SCOPUS:85061899612
SN - 2168-0485
VL - 7
SP - 5486
EP - 5493
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
IS - 5
ER -