C=C-Ene-Reductases Reduce the C=N Bond of Oximes.
C=C-Ene-Reductases Reduce the C=N Bond of Oximes.
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DOI：
10.1021/acscatal.0c03755
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发表时间：
2020-11-20
期刊：
影响因子：
12.9
通讯作者：
Kroutil W
中科院分区：
文献类型：
--
作者：
Velikogne S;Breukelaar WB;Hamm F;Glabonjat RA;Kroutil W
虽然已经发现了许多反应的酶，但仍然有一些转化是未知的酶。例如，没有一种明确的酶被描述用于还原肟类的C=N键，只有整个生物体被描述。在这种酶促还原的情况下，可以得到(手性)胺。我们偶然发现，烯基还原酶(ERs)可以将酮基和酯基附近的肟基还原为中间氨基。ERs是众所周知的用于还原活化的烯烃的酶，如α，β-不饱和酮。对于这里使用的特定底物，胺中间体会自发地进一步与四取代吡嗪反应。这种还原反应代表了内质网出人意料的混杂活动，扩大了使用酶转化的工具箱。
Although enzymes have been found for many reactions, there are still transformations for which no enzyme is known. For instance, not a single defined enzyme has been described for the reduction of the C=N bond of an oxime, only whole organisms. Such an enzymatic reduction of an oxime may give access to (chiral) amines. By serendipity, we found that the oxime moiety adjacent to a ketone as well as an ester group can be reduced by ene-reductases (ERs) to an intermediate amino group. ERs are well-known enzymes for the reduction of activated alkenes, as of α,β-unsaturated ketones. For the specific substrate used here, the amine intermediate spontaneously reacts further to tetrasubstituted pyrazines. This reduction reaction represents an unexpected promiscuous activity of ERs expanding the toolkit of transformations using enzymes.
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影响因子：
3.9
作者：
Dobrijevic, Dragana;Benhamou, Laure;Aliev, Abil E.;Mendez-Sanchez, Daniel;Dawson, Natalie;Baud, Damien;Tappertzhofen, Nadine;Moody, Thomas S.;Orengo, Christine A.;Hailes, Helen C.;Ward, John M.
通讯作者：
Ward, John M.
影响因子：
6.1
作者：
AKIYAMA, T;ENOMOTO, Y;SHIBAMOTO, T
通讯作者：
SHIBAMOTO, T
影响因子：
--
作者：
Brenna, Elisabetta;Crotti, Michele;Santangelo, Sara
通讯作者：
Santangelo, Sara
影响因子：
3.6
作者：
Brenna, Elisabetta;Gatti, Francesco G.;Sacchetti, Alessandro
通讯作者：
Sacchetti, Alessandro
影响因子：
9.8
作者：
Durchschein, Katharina;Silva, Bianca Ferreira-da;Faber, Kurt
通讯作者：
Faber, Kurt