Expanding the Biocatalytic Toolbox with a New Type of ene/yne-Reductase from Cyclocybe aegerita

Expanding the Biocatalytic Toolbox with a New Type of ene/yne-Reductase from Cyclocybe aegerita
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DOI:
10.1002/cctc.202002011
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发表时间:
2021-02-19
期刊:
影响因子:
4.5
通讯作者:
Ruhl, Martin
Ruhl, Martin
中科院分区:
化学3区
文献类型:
--
作者:
Karrer, Dominik;Gand, Martin;Ruhl, Martin

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本研究介绍了一种来自Cyclocybe aegerita的新型烯/炔还原酶,其底物范围广泛,包括脂肪族和芳香族烯烃/炔烃,其中脂肪族C8-烯酮、C8-烯醛和芳香族硝基烯烃是优选的底物。通过比较烯烃和炔烃,观察到炔烃的转化率降低了 2 倍。此外,可以表明,炔烃还原是通过将炔缓慢还原为烯烃,然后快速还原为相应的烷烃来进行的。没有观察到烯烃的积累。此外,α、β、γ、δ-不饱和烯醛的α、β位双键发生区域选择性还原。这以及首次将不同脂肪族和芳香族炔烃生物催化还原为烷烃,强调了这种生物催化剂的新颖性。因此,通过对新烯还原酶 CaeEnR1 的研究,公开了一个有前途的底物范围,可以想象,它描述了化学景观中此类反应的广泛发生。
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 similar to 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 alpha,beta-position of alpha,beta,gamma,delta-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.