Title

Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia.

Authors

Vilím, Jan; Knaus, Tanja; Mutti, Francesco G.

Abstract

We report an unprecedented catalytically promiscuous activity of the copper‐dependent enzyme galactose oxidase. The enzyme catalyses the one‐pot conversion of alcohols into the related nitriles under mild reaction conditions in ammonium buffer, consuming ammonia as the source of nitrogen and dioxygen (from air at atmospheric pressure) as the only oxidant. Thus, this green method does not require either cyanide salts, toxic metals, or undesired oxidants in stoichiometric amounts. The substrate scope of the reaction includes benzyl and cinnamyl alcohols as well as 4‐ and 3‐pyridylmethanol, giving access to valuable chemical compounds. The oxidation proceeds through oxidation from alcohol to aldehyde, in situ imine formation, and final direct oxidation to nitrile.

Subjects

GALACTOSE oxidase; NITRILES; ALCOHOL oxidation; AMMONIA; AMIDES; ALDEHYDES; BIOCATALYSIS

Publication

Angewandte Chemie, 2018, Vol 130, Issue 43, p14436

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.201809411