Engineering Neuroglobin for Synthesis of Chiral Organoborons via Carbene B-H Insertion

文献类型： 外文期刊

第一作者： Sun, Li-Juan

作者： Sun, Li-Juan;Gao, Shu-Qin;Lin, Ying-Wu;Wang, Huamin;Niu, Wenjing;Lin, Ying-Wu;Xu, Jia-Kun

作者机构：

期刊名称：ORGANIC LETTERS （ 影响因子：5.0； 五年影响因子：4.6 ）

ISSN： 1523-7060

年卷期： 2024 年 26 卷 41 期

页码：

收录情况： SCI

摘要： Organoborons have recently received much attention, while a biocatalytic platform for the synthesis of chiral organoborons is limited only to Rma cytochrome c. In this study, we exploited the other heme protein, neuroglobin (Ngb), and engineered a quadruple mutant, A15C/H64G/V68F/F28M Ngb, by redesigning the heme active site using the structural information on A15C Ngb and molecular docking studies. The enzyme was shown to be efficient in catalyzing carbene transfer B-H insertion reactions between pyridine/quinoline boranes and benzyl 2-diazopropanoates and their derivatives (29 examples). The designed cavity in the heme distal site favors the binding of large volume substrates such as those containing a quinoline, naphthyl, or biphenyl group. As further determined by the X-ray crystallography of 6c, the chiral products are in the R-configuration, with up to 98:2 e.r. Furthermore, both the whole cell and cell lysate containing the enzyme are reactive toward the B-H insertion reactions. This study presents a convenient biocatalytic platform that may be generally applicable for the synthesis of functional chiral organoborons.

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