黄素-N5-氧化物：黄素酶学中的一种新型催化基序。
Flavin-N5-oxide: A new, catalytic motif in flavoenzymology.
作者信息
Adak Sanjoy, Begley Tadhg P
机构信息
Department of Chemistry, Texas A&M University, College Station, TX 77843, United States.
Department of Chemistry, Texas A&M University, College Station, TX 77843, United States.
出版信息
Arch Biochem Biophys. 2017 Oct 15;632:4-10. doi: 10.1016/j.abb.2017.08.001. Epub 2017 Aug 5.
Abstract
Flavin-N5-oxide is a recently discovered intermediate used by EncM (1,3-diketone oxidation), DszA (sulfone monooxygenase) and RutA (amide monooxygenase). This review describes the mechanism of these enzymes and proposes criteria for the identification of additional Flavin-N5-oxide dependent enzymes.
摘要
黄素 - N5 - 氧化物是最近发现的一种中间体，被EncM（1,3 - 二酮氧化酶）、DszA（砜单加氧酶）和RutA（酰胺单加氧酶）所利用。本综述描述了这些酶的作用机制，并提出了鉴定其他黄素 - N5 - 氧化物依赖性酶的标准。
相似文献
1
Flavin-N5-oxide: A new, catalytic motif in flavoenzymology.黄素-N5-氧化物：黄素酶学中的一种新型催化基序。
Arch Biochem Biophys. 2017 Oct 15;632:4-10. doi: 10.1016/j.abb.2017.08.001. Epub 2017 Aug 5.
2
Flavin-N5-oxide intermediates in dibenzothiophene, uracil, and hexachlorobenzene catabolism.二苯并噻吩、尿嘧啶和六氯苯分解代谢中的黄素 - N5 - 氧化物中间体。
Methods Enzymol. 2019;620:455-468. doi: 10.1016/bs.mie.2019.03.020. Epub 2019 Apr 17.
3
Insights into the enzymatic formation, chemical features, and biological role of the flavin-N5-oxide.黄素-N5-氧化物的酶促形成、化学特征和生物学作用的研究进展。
Curr Opin Chem Biol. 2018 Dec;47:47-53. doi: 10.1016/j.cbpa.2018.08.003. Epub 2018 Aug 27.
4
Oxygen-transfer reactions by enzymatic flavin-N oxygen adducts-Oxidation is not a must.酶黄素-N 氧加合物的氧转移反应——氧化并非必需。
Curr Opin Chem Biol. 2024 Jun;80:102464. doi: 10.1016/j.cbpa.2024.102464. Epub 2024 May 12.
5
Preparation and Characterization of the Favorskiiase Flavoprotein EncM and Its Distinctive Flavin-N5-Oxide Cofactor.法沃斯基酶黄素蛋白EncM的制备与表征及其独特的黄素-N5-氧化物辅因子
Methods Enzymol. 2018;604:523-540. doi: 10.1016/bs.mie.2018.01.036. Epub 2018 Mar 16.
6
Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases.单组分和双组分黄素依赖性芳香族羟化酶催化过程中涉及的动力学
Biochem Biophys Res Commun. 2005 Dec 9;338(1):590-8. doi: 10.1016/j.bbrc.2005.09.081. Epub 2005 Sep 26.
7
The devil is in the details: The chemical basis and mechanistic versatility of flavoprotein monooxygenases.魔鬼在细节中：黄素蛋白单加氧酶的化学基础和机制多样性。
Arch Biochem Biophys. 2021 Feb 15;698:108732. doi: 10.1016/j.abb.2020.108732. Epub 2020 Dec 24.
8
The FMN-dependent two-component monooxygenase systems.依赖黄素单核苷酸的双组分单加氧酶系统。
Arch Biochem Biophys. 2010 May;497(1-2):1-12. doi: 10.1016/j.abb.2010.02.007. Epub 2010 Mar 1.
9
Structural and chemical trapping of flavin-oxide intermediates reveals substrate-directed reaction multiplicity.结构和化学捕获黄素氧化物中间体揭示了底物导向的反应多样性。
Protein Sci. 2020 Jul;29(7):1655-1666. doi: 10.1002/pro.3879. Epub 2020 May 26.
10
New frontiers in flavin-dependent monooxygenases.黄素依赖单加氧酶的新领域。
Arch Biochem Biophys. 2021 Mar 15;699:108765. doi: 10.1016/j.abb.2021.108765. Epub 2021 Jan 16.
引用本文的文献
1
Crystal Structure, Modeling, and Identification of Key Residues Provide Insights into the Mechanism of the Key Toxoflavin Biosynthesis Protein ToxD.关键毒素黄素生物合成蛋白ToxD的晶体结构、建模及关键残基鉴定为其作用机制提供见解
Biochemistry. 2025 Mar 18;64(6):1199-1211. doi: 10.1021/acs.biochem.4c00421. Epub 2025 Mar 6.
2
Modulating Enzyme Function Dynamic Allostery within Biliverdin Reductase B.调节酶功能：胆红素还原酶B中的动态别构作用
Front Mol Biosci. 2021 May 20;8:691208. doi: 10.3389/fmolb.2021.691208. eCollection 2021.
3
Structural and chemical trapping of flavin-oxide intermediates reveals substrate-directed reaction multiplicity.结构和化学捕获黄素氧化物中间体揭示了底物导向的反应多样性。
Protein Sci. 2020 Jul;29(7):1655-1666. doi: 10.1002/pro.3879. Epub 2020 May 26.
4
Two-Component FAD-Dependent Monooxygenases: Current Knowledge and Biotechnological Opportunities.双组分黄素腺嘌呤二核苷酸依赖性单加氧酶：当前认知与生物技术应用前景
Biology (Basel). 2018 Aug 2;7(3):42. doi: 10.3390/biology7030042.
本文引用的文献
1
RutA-Catalyzed Oxidative Cleavage of the Uracil Amide Involves Formation of a Flavin-N5-oxide.鲁特A催化的尿嘧啶酰胺氧化裂解涉及黄素-N5-氧化物的形成。
Biochemistry. 2017 Jul 25;56(29):3708-3709. doi: 10.1021/acs.biochem.7b00493. Epub 2017 Jul 10.
2
Flavin-catalyzed redox tailoring reactions in natural product biosynthesis.天然产物生物合成中的黄素催化氧化还原修饰反应。
Arch Biochem Biophys. 2017 Oct 15;632:20-27. doi: 10.1016/j.abb.2017.06.008. Epub 2017 Jun 12.
3
Flavins as Covalent Catalysts: New Mechanisms Emerge.黄素作为共价催化剂：新机制浮现。
Trends Biochem Sci. 2017 Jun;42(6):457-469. doi: 10.1016/j.tibs.2017.02.005. Epub 2017 Mar 6.
4
Sweating the assets of flavin cofactors: new insight of chemical versatility from knowledge of structure and mechanism.探究黄素辅因子的特性：基于结构与机制知识的化学多功能性新见解
Curr Opin Struct Biol. 2016 Dec;41:19-26. doi: 10.1016/j.sbi.2016.05.014. Epub 2016 Jun 3.
5
Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate.二苯并噻吩通过黄素-N5-氧化物中间体进行代谢。
J Am Chem Soc. 2016 May 25;138(20):6424-6. doi: 10.1021/jacs.6b00583. Epub 2016 May 10.
6
Unusual flavoenzyme catalysis in marine bacteria.海洋细菌中不同寻常的黄素酶催化作用。
Curr Opin Chem Biol. 2016 Apr;31:31-9. doi: 10.1016/j.cbpa.2016.01.001. Epub 2016 Jan 21.
7
Biochemical Establishment and Characterization of EncM's Flavin-N5-oxide Cofactor.EncM黄素-N5-氧化物辅因子的生化鉴定与表征
J Am Chem Soc. 2015 Jul 1;137(25):8078-85. doi: 10.1021/jacs.5b03983. Epub 2015 Jun 19.
8
Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement.黄素介导的双重氧化控制酶促 Favorskii 重排。
Nature. 2013 Nov 28;503(7477):552-556. doi: 10.1038/nature12643. Epub 2013 Oct 27.
9
Flavoenzymes: versatile catalysts in biosynthetic pathways.黄酶：生物合成途径中的多功能催化剂。
Nat Prod Rep. 2013 Jan;30(1):175-200. doi: 10.1039/c2np20069d.
10
Baeyer-Villiger monooxygenases: more than just green chemistry.拜耳-维利格单加氧酶：不止于绿色化学。
Chem Rev. 2011 Jul 13;111(7):4165-222. doi: 10.1021/cr1003437. Epub 2011 May 4.
Zotero 插件