Advances of Haloperoxidases-Catalyzed Green Halogenation Reactions

doi:10.6023/cjoc202009007

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 959-968.DOI: 10.6023/cjoc202009007 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 13

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

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

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

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

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

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

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

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 ℃

Figure 9. Sulfoxidation reactions catalyzed by haloperoxidases

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

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

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

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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