Synthesis of C-N bonds by nicotinamide-dependent oxidoreductase: an overview.

IF 8.1 2区工程技术 Q1 BIOTECHNOLOGY & APPLIED MICROBIOLOGY

Critical Reviews in Biotechnology Pub Date : 2024-09-04 DOI:10.1080/07388551.2024.2390082

Tianfu Wu, Wanqing Wei, Changzheng Gao, Jing Wu, Cong Gao, Xiulai Chen, Liming Liu, Wei Song

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引用次数: 0

Abstract

Compounds containing chiral C-N bonds play a vital role in the composition of biologically active natural products and small pharmaceutical molecules. Therefore, the development of efficient and convenient methods for synthesizing compounds containing chiral C-N bonds is a crucial area of research. Nicotinamide-dependent oxidoreductases (NDOs) emerge as promising biocatalysts for asymmetric synthesis of chiral C-N bonds due to their mild reaction conditions, exceptional stereoselectivity, high atom economy, and environmentally friendly nature. This review aims to present the structural characteristics and catalytic mechanisms of various NDOs, including imine reductases/ketimine reductases, reductive aminases, EneIRED, and amino acid dehydrogenases. Additionally, the review highlights protein engineering strategies employed to modify the stereoselectivity, substrate specificity, and cofactor preference of NDOs. Furthermore, the applications of NDOs in synthesizing essential medicinal chemicals, such as noncanonical amino acids and chiral amine compounds, are extensively examined. Finally, the review outlines future perspectives by addressing challenges and discussing the potential of utilizing NDOs to establish efficient biosynthesis platforms for C-N bond synthesis. In conclusion, NDOs provide an economical, efficient, and environmentally friendly toolbox for asymmetric synthesis of C-N bonds, thus contributing significantly to the field of pharmaceutical chemical development.

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烟酰胺依赖性氧化还原酶合成 C-N 键：概述。

含有手性 C-N 键的化合物在具有生物活性的天然产物和医药小分子的组成中发挥着重要作用。因此，开发高效便捷的方法来合成含有手性 C-N 键的化合物是一个至关重要的研究领域。烟酰胺依赖性氧化还原酶（NDOs）反应条件温和，具有优异的立体选择性、高原子经济性和环境友好性，是手性 C-N 键不对称合成的理想生物催化剂。本综述旨在介绍各种 NDO 的结构特征和催化机理，包括亚胺还原酶/酮亚胺还原酶、还原性胺酶、EneIRED 和氨基酸脱氢酶。此外，综述还重点介绍了为改变 NDOs 的立体选择性、底物特异性和辅助因子偏好而采用的蛋白质工程策略。此外，还广泛探讨了 NDOs 在合成非典型氨基酸和手性胺化合物等基本医药化学品方面的应用。最后，本综述通过应对挑战和讨论利用 NDOs 建立 C-N 键合成的高效生物合成平台的潜力，概述了未来的发展前景。总之，NDO 为 C-N 键的不对称合成提供了一个经济、高效和环保的工具箱，从而为药物化学开发领域做出了重大贡献。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Critical Reviews in Biotechnology 工程技术-生物工程与应用微生物

CiteScore

20.80

自引率

1.10%

发文量

审稿时长

4.8 months

期刊介绍： Biotechnological techniques, from fermentation to genetic manipulation, have become increasingly relevant to the food and beverage, fuel production, chemical and pharmaceutical, and waste management industries. Consequently, academic as well as industrial institutions need to keep abreast of the concepts, data, and methodologies evolved by continuing research. This journal provides a forum of critical evaluation of recent and current publications and, periodically, for state-of-the-art reports from various geographic areas around the world. Contributing authors are recognized experts in their fields, and each article is reviewed by an objective expert to ensure accuracy and objectivity of the presentation.