烯烃还原酶与有机光催化剂协同催化实现烯烃的自由基氢叠氮化

doi:10.1016/S1872-2067(26)65025-5

催化学报 ›› 2026, Vol. 85: 88-95.DOI: 10.1016/S1872-2067(26)65025-5

烯烃还原酶与有机光催化剂协同催化实现烯烃的自由基氢叠氮化

余进海^a^,^b^,¹(), 郝英迪^b^,¹, 任樱枝^b, 赵贝贝^b, 马戈^b, 郭子豪^b, 张艳^b(), 黄小强^b()

^a 南京工业大学生物与制药工程学院, 江苏南京 211816
^b 南京大学前沿交叉科学研究中心, 化学化工学院, 化学和生物医药创新中心, 配位化学全国重点实验室, 江苏南京 210023

收稿日期:2025-12-10 接受日期:2026-01-26 出版日期:2026-06-18 发布日期:2026-05-18
通讯作者: *电子信箱: huangx513@nju.edu.cn (黄小强),
njuzy@nju.edu.cn (张艳),
njuyujinhai@nju.edu.cn (余进海).
作者简介:
¹共同第一作者.
基金资助:
国家重点研发计划(2023YFA1506500);国家自然科学基金(22225703);国家自然科学基金(22277053);中央高校基本科研业务费(KG202503);教育部基础学科与交叉学科突破计划(JYB2025XDXM507)

Radical hydroazidation of alkene enabled by synergistic photobiocatalysis combining ene-reductase with an organophotocatalyst

Jinhai Yu^a^,^b^,¹(), Yingdi Hao^b^,¹, Yingzhi Ren^b, Beibei Zhao^b, Ge Ma^b, Zihao Guo^b, Yan Zhang^b(), Xiaoqiang Huang^b()

^a College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, Jiangsu, China
^b State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Frontier Interdisciplinary Science Research Center, Nanjing University, Nanjing 210023, Jiangsu, China

Received:2025-12-10 Accepted:2026-01-26 Online:2026-06-18 Published:2026-05-18
Contact: *E-mail: huangx513@nju.edu.cn (X. Huang),
njuzy@nju.edu.cn (Y. Zhang),
njuyujinhai@nju.edu.cn (J. Yu).
About author:
¹Contributed equally to this work.
Supported by:
National Key Research and Development Program of China(2023YFA1506500);National Natural Science Foundation of China(22225703);National Natural Science Foundation of China(22277053);Fundamental Research Funds for the Central Universities(KG202503);Fundamental and Interdisciplinary Disciplines Breakthrough Plan of the Ministry of Education of China(JYB2025XDXM507)

摘要/Abstract

摘要：

光生物催化融合了光催化与生物催化的优势, 显著拓展了酶催化非天然转化的适用范围. 其中, 烯烃还原酶与光催化协同体系已成功用于多种净还原型、氧化还原中性及净氧化型反应, 但实现氧化还原中性、高对映选择性的碳-叠氮键构建, 仍面临重大挑战. 烯烃的直接氢叠氮化是合成叠氮类化合物有效的方法之一, 然而高对映选择性的自由基氢叠氮化反应迄今尚未实现. 为此, 本研究旨在发展一种新型协同光生物催化体系, 在温和条件下直接实现烯烃的对映选择性氢叠氮化, 为手性叠氮化合物的高效、可持续合成提供新策略.

本研究开发了一种由烯烃还原酶和有机光催化剂(曙红Y或荧光桃红B)组成的光生物协同催化体系, 在可见光(500-510 nm)照射下, 成功实现了多种烯烃的高效、高对映选择氢叠氮化反应. 首先通过对烯烃还原酶与有机光催化剂种类的筛选, 得到来自Yersinia bercovieri的YersER与曙红Y或荧光桃红B的组合显示出优异的催化性能. 在优化后的条件下, 能够以83%的产率和97:3的对映体比(e.r.)得到(R)-构型模型产物2a. 底物拓展实验表明, 无论是给电子基团还是吸电子基团取代的芳基烯烃均可顺利发生反应, 得到相应的目标手性叠氮产物. 该方法也适用于环状烯烃以及含有连续双手性中心的烯烃底物. 并且, 该策略实现了0.1 mmol规模合成, 所得的产物可通过点击化学或还原等衍生化反应, 转化为手性三氮唑或手性伯胺等含氮化合物. 荧光淬灭实验表明, 光激发的酶复合物是氧化N₃⁻生成N₃•的关键. 自由基捕获实验证实了苄基自由基中间体的存在. 基于上述结果, 提出了可能的反应机理. 首先, 在可见光照射下, 激发态酶-光催化剂复合物触发单电子氧化过程, 生成叠氮自由基N₃•与半醌态黄素辅因子FMN_sq. 随后, N₃•加成至碳碳双键, 形成前手性苄基自由基中间体. 最终, 酶活性位点内的FMN_sq介导的HAT过程生成对映体富集的产物, 同时再生基态FMN_ox.

综上, 本文开发一种光生物协同催化体系, 实现了烯烃的高对映选择性自由基氢叠氮化. 这项工作不仅拓展了光驱动黄素蛋白的合成潜力, 也为利用天然酶介导挑战性的杂原子自由基反应提供了新范式, 进一步证明生物催化与化学催化的合理整合, 能够解锁更多未知的非天然、高选择性转化反应.

关键词: 光生物催化, 烯烃还原酶, 有机染料, 单电子转移, 氢叠氮化反应

Abstract:

The integration of biocatalysis with photocatalysis provides a powerful platform for accessing non-natural biotransformations. While diverse net-reductive photobiocatalysis has been achieved with ene-reductases (EREDs), the redox-neutral construction of C-N₃ (C-azide) bond remains an underexplored challenge. Herein, we develop a synergistic photobiocatalytic system comprising an ERED and an organic dye that enables the enantioselective hydroazidation of alkenes. Upon visible-light-excitation, the organic dye promotes the single-electron oxidation of NaN₃ to generate N₃• radical. This radical is then trapped by alkene, and the ensuing prochiral radical is precisely terminated by enzyme-controlled hydrogen-atom transfer (HAT), affording enantioenriched alkyl azides in excellent yield (up to 99%) and enantioselectivity (up to > 99.5:0.5 e.r.). This method applies to a variety of substituted alkenes, part of which bear vicinal stereocenters. Mechanistic studies, including ultraviolet-visible absorbance measurements, and luminescence quenching experiments, suggest a synergistic effect among the enzyme-bound flavin, organophotocatalyst, as well as sodium azide and explain the origin of stereochemical control. This work establishes a new biocatalytic strategy for the formation of C-N₃ bonds and expands the synthetic potential of light-driven flavoproteins.

Key words: Photobiocatalysis, Ene-reductase, Organic dye, Single-electron transfer, Redox-neutral hydroazidation

余进海, 郝英迪, 任樱枝, 赵贝贝, 马戈, 郭子豪, 张艳, 黄小强. 烯烃还原酶与有机光催化剂协同催化实现烯烃的自由基氢叠氮化[J]. 催化学报, 2026, 85: 88-95.

Jinhai Yu, Yingdi Hao, Yingzhi Ren, Beibei Zhao, Ge Ma, Zihao Guo, Yan Zhang, Xiaoqiang Huang. Radical hydroazidation of alkene enabled by synergistic photobiocatalysis combining ene-reductase with an organophotocatalyst[J]. Chinese Journal of Catalysis, 2026, 85: 88-95.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(26)65025-5

https://www.cjcatal.com/CN/Y2026/V85/I6/88

图/表 5

Fig. 1. Developing biocatalytic strategies to access organic azides. (a) Photoexcited ene-reductases catalyzed redox-neutral radical hydrofunctionalization. (b) Biocatalytic approaches for azidation of alkenes. (c) This work: enantioselective hydroazidation of alkenes by synergistic dual photo/ene-reductase catalysis. EREDs = ene-reductases, FMNox = oxidized form of flavin mononucleotide, FMNox* = excited state FMNox, SET = single electron transfer, HAT = hydrogen-atom transfer, cyan LEDs, an emission wavelength centered in the 500-510 nm range.

Fig. 2. Development of the photobiocatalytic radical hydroazidation of alkenes. (a) Discovery of hydroazidation activity using ene-reductase-based photobiocatalytic single catalysis. (b) Photocatalyst effects on enantioselective radical hydroazidation of alkenes. (c) Evaluation of the key reaction parameters. aConditions: 1a (0.005 mmol), NaN3 (0.025 mmol), ERED (1.0 mol%), Eosin Y (5 mol%), DMSO (5 v/v %) in Tris buffer (50 mmol L-1, pH 6.5) were stirred at room temperature for 12 hours under N2 atmosphere with the irradiation of cyan LEDs (500-510 nm). The total volume of the reaction is 1 mL. bYield was determined by HPLC. cEnantiomeric ratio (e.r.) was determined by HPLC analysis on a chiral stationary phase. n.d. = not determined, YersER = ene-reductase from Yersinia bercovieri, PETNr = ene-reductase from Enterobacter cloacae, CsER = ene-reductase from Caulobacter segnis, OYE1 = ene-reductase from Saccharomyces pastorianus, GluER = ene-reductase from Gluconobacter oxydans.

Fig. 3. The scope and derivatization of the photobiocatalytic products. The standard conditions shown in Fig. 2(c), entry 1, were applied. HPLC determined yields as the average of duplicates using two different batches of enzyme. e.r. = enantiomeric ratio was determined by HPLC analysis on a chiral stationary phase. aYields were obtained using Eosin Y as the photocatalyst. bYields were obtained using Phloxine B as the photocatalyst. cIndicates isolated yield based on a 0.1 mmol scale-up reaction.

Fig. 4. Mechanistic studies. (a) UV-vis absorption spectra. YersER (0.05 mmol L-1), Eosin Y (0.0125 mmol L-1), NaN3 (25 mmol L-1). (b) Luminescence quenching experiments. NaN3 (0-25 mmol L-1) was added to the YersER solution (0.05 mmol L-1) in Tris buffer. Samples were excited at 455 nm, and emission was measured at 540 nm (c) Transformations with apoenzyme. (d) Radical trapping experiment with TEMPO. (e) Deuterium labeling experiments.

Fig. 5. Proposed catalytic mechanism for the photobiocatalytic hydroazidation. FMNox/sq = oxidation/semiquinone state of flavin mononucleotide, HAT = hydrogen-atom transfer.

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烯烃还原酶与有机光催化剂协同催化实现烯烃的自由基氢叠氮化

Radical hydroazidation of alkene enabled by synergistic photobiocatalysis combining ene-reductase with an organophotocatalyst

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