Formation and Cleavage of C–C Bonds by Enzymatic Oxidation–Reduction Reactions,Chemical Reviews

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Formation and Cleavage of C–C Bonds by Enzymatic Oxidation–Reduction Reactions
Chemical Reviews ( IF 51.4 ) Pub Date : 2018-06-22 00:00:00 , DOI: 10.1021/acs.chemrev.8b00031
F. Peter Guengerich _{1,

2} , Francis K. Yoshimoto _{1,

2}

Affiliation

Many oxidation–reduction (redox) enzymes, particularly oxygenases, have roles in reactions that make and break C–C bonds. The list includes cytochrome P450 and other heme-based monooxygenases, heme-based dioxygenases, nonheme iron mono- and dioxygenases, flavoproteins, radical S-adenosylmethionine enzymes, copper enzymes, and peroxidases. Reactions involve steroids, intermediary metabolism, secondary natural products, drugs, and industrial and agricultural chemicals. Many C–C bonds are formed via either (i) coupling of diradicals or (ii) generation of unstable products that rearrange. C–C cleavage reactions involve several themes: (i) rearrangement of unstable oxidized products produced by the enzymes, (ii) oxidation and collapse of radicals or cations via rearrangement, (iii) oxygenation to yield products that are readily hydrolyzed by other enzymes, and (iv) activation of O₂ in systems in which the binding of a substrate facilitates O₂ activation. Many of the enzymes involve metals, but of these, iron is clearly predominant.

中文翻译：

酶氧化还原反应形成和断裂CC键

许多氧化还原（redox）酶，特别是加氧酶，在形成和破坏CC键的反应中都起作用。该列表包括细胞色素P450和其他基于血红素的单加氧酶，基于血红素的双加氧酶，非血红素铁单加氧和双加氧酶，黄素蛋白，S自由基-腺苷甲硫氨酸酶，铜酶和过氧化物酶。反应涉及类固醇，中间代谢，二级天然产物，药物以及工业和农业化学品。通过（i）双自由基的耦合或（ii）生成不稳定的重排产物可以形成许多C–C键。C–C裂解反应涉及多个主题：（i）由酶产生的不稳定氧化产物的重排，（ii）自由基或阳离子通过重排的氧化和瓦解，（iii）氧化产生易于被其他酶水解的产物，和（iv）O的活化₂中系统，其中的底物功能有助于ö结合₂活化。许多酶都涉及金属，但其中显然铁占主导地位。

更新日期：2018-06-22

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