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Expanding the Biocatalytic Toolbox with a New Type of ene/yne‐Reductase from Cyclocybe aegerita
Author(s) -
Karrer Dominik,
Gand Martin,
Rühl Martin
Publication year - 2021
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.202002011
Subject(s) - alkene , alkyne , chemistry , biocatalysis , regioselectivity , ene reaction , substrate (aquarium) , stereochemistry , double bond , combinatorial chemistry , organic chemistry , reaction mechanism , catalysis , oceanography , geology
This study introduces a new type of ene/yne‐reductase from Cyclocybe aegerita with a broad substrate scope including aliphatic and aromatic alkenes/alkynes from which aliphatic C8‐alkenones, C8‐alkenals and aromatic nitroalkenes were the preferred substrates. By comparing alkenes and alkynes, a ∼2‐fold lower conversion towards alkynes was observed. Furthermore, it could be shown that the alkyne reduction proceeds via a slow reduction of the alkyne to the alkene followed by a rapid reduction to the corresponding alkane. An accumulation of the alkene was not observed. Moreover, a regioselective reduction of the double bond in α , β ‐position of α,β,γ,δ‐ unsaturated alkenals took place. This as well as the first biocatalytic reduction of different aliphatic and aromatic alkynes to alkanes underlines the novelty of this biocatalyst. Thus with this study on the new ene‐reductase CaeEnR1, a promising substrate scope is disclosed that describes conceivably a broad occurrence of such reactions within the chemical landscape.