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Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent “Ene”-Reductases
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2021-11-16 , DOI: 10.1021/jacs.1c09828
Xin Gao 1 , Joshua R Turek-Herman 1, 2 , Young Joo Choi 1 , Ryan D Cohen 3 , Todd K Hyster 1, 2
Affiliation  

α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent ‘ene’-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.

中文翻译:

工程黄素依赖性“烯”还原酶光酶促合成 α-叔胺

α-叔胺是药学上重要分子中的常见基序,但使用不对称催化制备具有挑战性。在这里,我们展示了工程化的黄素依赖性“烯”还原酶 (ERED) 可以催化自由基加成到肟中以制备该基序。两种不同的 ERED 演变成具有高立体选择性的这种转化的有效催化剂。机理研究表明,肟有助于在底物和辅助因子之间形成酶模板化电荷转移复合物。这些产品可以进一步衍生化以制备各种图案,突出了 ERED 光酶催化有机合成的多功能性。
更新日期:2021-12-01
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