卤过氧化物酶在绿色卤化反应中的研究进展

doi:10.6023/cjoc202009007

有机化学 ›› 2021, Vol. 41 ›› Issue (3): 959-968.DOI: 10.6023/cjoc202009007 上一篇下一篇

综述与进展

卤过氧化物酶在绿色卤化反应中的研究进展

曾志刚^a^,^b, 桑贤轲^a, 袁波^c, 吴鸣虎^a^,^b^,^*(), 张武元^c^,^*()

a 湖北科技学院核技术与化学生物学院湖北咸宁 437100
b 辐射化学与功能材料湖北省重点实验室湖北咸宁 437100
c 西安交通大学化学工程与技术学院西安 710049

收稿日期:2020-09-02 修回日期:2020-09-26 发布日期:2020-10-15
通讯作者: 吴鸣虎, 张武元
基金资助:
国家自然科学基金(31601675); 西安交通大学青年拔尖人才计划及青年跟踪计划和湖北科技学院博士启动基金(BK201821)

Advances of Haloperoxidases-Catalyzed Green Halogenation Reactions

Zhigang Zeng^a^,^b, Xianke Sang^a, Bo Yuan^c, Minghu Wu^a^,^b^,^*(), Wuyuan Zhang^c^,^*()

a School of Nuclear Technology and Chemistry & Biology, Hubei University of Science and Technology,Xianning, Hubei 437100
b Hubei Key Laboratory of Radiation Chemistry and Functional Materials, Xianning, Hubei 437100
c School of Chemical Engineering and Technology, Xi'an Jiaotong University, Xi'an 710049

Received:2020-09-02 Revised:2020-09-26 Published:2020-10-15
Contact: Minghu Wu, Wuyuan Zhang
About author:
* Corresponding authors. E-mail: w.zhang@xjtu.edu.cn;
minghuwu@163.com
Supported by:
National Natural Science Foundation of China(31601675); Youth Top Talent Program and Tracking Support Program of Xi'an Jiaotong University, and the Ph.D. Start-up Fund of Hubei University of Science and Technology(BK201821)

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摘要/Abstract

卤化反应是一类极其重要的有机合成反应, 在实验室研究和化工生产领域占据重要地位. 传统卤化反应因存在使用有毒有害试剂、反应缺乏选择性等问题而亟待改进, 生物酶催化策略则为突破上述瓶颈提供了可能. 自然界已经进化出多种可对有机物中催化引入卤素的卤化酶. 酶催化卤化反应的突出优势在于常温常压下, 可使用来源温和的卤素进行高效的催化反应. 催化范围包括卤化、羟卤化、卤环合和氧化脱羧等多种具有挑战性的反应. 鉴于酶催化卤化反应展示出巨大的潜力, 从催化活性、酶稳定性、底物浓度、催化范围等几个方面着重介绍了卤过氧化物酶在绿色卤化反应中的最新研究进展, 为进一步开发绿色的卤化酶催化卤化反应提供参考.

关键词: 卤过氧化物酶, 生物催化, 卤化反应, 有机合成, 绿色化学

Halogenation reaction is one of the key reactions in organic synthesis, which acts pivotal part both in laboratory study and industrial applications. Traditional halogenation reactions rely on the use of toxic and hazardous reagents with low selectivity. The enzymatic catalysis bears enormous possibilities to overcome abovementioned bottlenecks remaining in traditional halogenation reactions. Nature has evolved a variety of halogenases that are capable of catalyzing the introduction of halogen atoms in organic substrates. The particular advantage of enzymatic catalysis is that it enables the efficient halogenation reactions occurring at common temperature and pressure with the use of mild halogen sources. The enabled challenging reactions range from halogenation, halohydroxylation, halocyclization to oxidative decarboxylation. In view of the significant potential of enzymatic catalysis in halogenation reactions, the recent advances of halogenase-catalyzed green synthesis are introduced from the perspective of catalytic activity, enzyme stability, substrate concentration, catalytic scope and so on. It is hoped to raise further inspirations in the development of green halogenation reactions catalyzed by halogenases.

Key words: haloperoxidases, biocatalysis, halogenation reactions, organic synthesis, green chemistry

引用此文

曾志刚, 桑贤轲, 袁波, 吴鸣虎, 张武元. 卤过氧化物酶在绿色卤化反应中的研究进展[J]. 有机化学, 2021, 41(3): 959-968.

Zhigang Zeng, Xianke Sang, Bo Yuan, Minghu Wu, Wuyuan Zhang. Advances of Haloperoxidases-Catalyzed Green Halogenation Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 959-968.

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图/表 13

图1. 血红素依赖型(a)和钒依赖型(b)卤过氧化物酶氧化卤素的机理

Figure 1. mechanism of Heme- and vanadium-dependent haloperoxidases catalyzed oxidation of halogens

图2. VBPO催化环己烯的环氧化反应及反应机理

Figure 2. VBPO catalyzed epoxidation of cyclohexene and the reaction mechanism

图3. 卤过氧化物酶催化合成卤代芳烃的实例及反应的转化率(蓝色)和收率(绿色)[30,36-37]

Figure 3. Synthesis of halogenated arenes catalyzed by halo- peroxidases and the corresponding conversion (blue) and yield (green)

图4. VCPO催化苯乙烯磺酸钠的羟卤化反应的时间历程(底物●; 产物◆)

Figure 4. Time course of halohydroxylation of sodium styrene sulfonate catalyzed by VCPO (substrate●; product◆) Reaction conditions: aqueous (D2O, 0.1 mol?L–1 citrate buffer, pH 5.0), [sodium styrene sulfonate]=40 mmol?L–1, [KBr]=160 mmol?L–1, [CiVCPO]=100 nmol?L–1, T=25 ℃. The concentration of the substrate and product was determined by 1H NMR

图5. VCPO催化C=C的羟卤化反应的底物范围

Figure 5. Substrate scope of halohydroxylation of C=C double bond catalyzed by VCPO Reaction conditions: [CiVCPO]=100 nmol?L–1; [substrate]=40 mmol? L–1; [KX, X=Cl、Br]=160 mmol?L–1; [H2O2]=170 mmol?L–1, 0.1 mol? L–1 citrate buffer, pH 5.0, T=25 ℃, t=20 h. a isolated yield. b 1H NMR yield

图6. 由酶生成的活性次卤酸催化分子内的卤环化反应机理

Figure 6. Mechanism of the intramolecular halo-cyclization reaction catalyzed by the reactive hypohalites

图7. CiVCPO催化γ,δ-不饱和羧酸(醇)的环内酯化(环内醚化)反应的转化率(蓝色)和选择性(绿色)

Figure 7. CiVCPO catalyzed halo-cyclization reactions of γ,δ-unsaturated carboxylic acids (alcohols) and the corresponding conversion (blue) and selectivity (green)

图8. 谷氨酸(●)的氧化脱羧制备3-氰丙酸(◆)

Figure 8. Oxidative decarboxylation of glutamic acid (●) to synthesize 3-cyanopropionic acid (◆) Reaction conditions: [glutamic acid]=100 mmol?L–1, [NaBr]=5 mmol? L–1, [CiVCPO]=50 nmol?L–1, dose rate of H2O2 39 mmol?L–1?h–1, citrate buffer (20 mmol?L–1, pH 5.6), T=22 ℃

图9. 卤过氧化物酶催化磺氧化反应

Figure 9. Sulfoxidation reactions catalyzed by haloperoxidases

图10. LfCPO催化呋喃的氧化环扩张(Achmatowicz)反应(a)及其底物范围(b)

Figure 10. LfCPO-catalyzed oxidative ring-expansion (Achmatowicz) reactions of furans (a) and its substrate scope (b) Reaction conditions: [Glucose]=50 mmol?L–1, [Substrate]=10 mmol? L–1, [Glucose oxidase]=3.6 mmol?L–1, [Substrate]=10 mmol?L–1, [LfCPO] 0.41 mmol?L–1, 100 mmol?L–1 sodium citrate buffer (pH 5.5), 10% tert-butanol, r.t.

Catalyst	c/(mmol?L^–1)	TON^a/(mol?mol^–1)	TOF^a/s
CiVCPO^[30] [VVO(OMe)(MeOH)]^[51]	20 396	198000 7117	55 1
CiVCPO^[39] NH₄VO₃^[52] NH₄VO₃^[53] None (substrates and NBS only)^[54]	36 50 9 61	360000 0.5 0.9 n.a.	15 n.a. 0.00006 n.a.
CiVCPO^[46] $\text{WO}_{\text{4}}^{2}$ loaded on [Ni,Al]-LDH^[55-56]	5 125	277778 28	15 0.0005

表1. CiVCPO与传统化学催化剂在溴化反应和脱羧反应中的催化性能对比

Table 1. Comparison of the catalytic performance between CiVCPO and chemical counterparts in bromination and decarboxylation reactions

图11. 高原子经济性光催化氧化H2O[64]和CH3OH[65]原位生成H2O2级联过氧合酶催化(蓝色箭头代表氧化反应中电子流向)

Figure 11. High atom-efficient photocatalytic oxidation of H2O[64] and CH3OH[65]for the in situ generation of H2O2 and cascading with peroxygenases

图12. 水溶性蒽醌光催化氧化小分子醇生成H2O2与CiVCPO偶联催化百里香酚的溴代反应

Figure 12. Water soluble anthraquinone catalyzed simple alcohol oxidation for the in situ generation of H2O2 and cascading with CiVCPO for the bromination of thymol

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卤过氧化物酶在绿色卤化反应中的研究进展

Advances of Haloperoxidases-Catalyzed Green Halogenation Reactions

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