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本文引用的文献

1
Insights into the mechanism of flavoprotein-catalyzed amine oxidation from nitrogen isotope effects on the reaction of N-methyltryptophan oxidase.通过氮同位素效应研究N-甲基色氨酸氧化酶反应对黄素蛋白催化胺氧化机制的深入了解。
Biochemistry. 2007 Jun 26;46(25):7655-64. doi: 10.1021/bi700482h. Epub 2007 Jun 2.
2
Mechanistic studies of the flavoenzyme tryptophan 2-monooxygenase: deuterium and 15N kinetic isotope effects on alanine oxidation by an L-amino acid oxidase.黄素酶色氨酸2-单加氧酶的机制研究：氘和15N动力学同位素效应作用于L-氨基酸氧化酶对丙氨酸的氧化反应
Biochemistry. 2006 Dec 26;45(51):15844-52. doi: 10.1021/bi061894o.
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Crystal structure and mechanism of human lysine-specific demethylase-1.人类赖氨酸特异性去甲基化酶-1的晶体结构与作用机制
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Functional role of the "aromatic cage" in human monoamine oxidase B: structures and catalytic properties of Tyr435 mutant proteins.“芳香笼”在人单胺氧化酶B中的功能作用：Tyr435突变蛋白的结构与催化特性
Biochemistry. 2006 Apr 18;45(15):4775-84. doi: 10.1021/bi051847g.
5
Crystal structures of nitroalkane oxidase: insights into the reaction mechanism from a covalent complex of the flavoenzyme trapped during turnover.硝基烷氧化酶的晶体结构：从周转过程中捕获的黄素酶共价复合物洞察反应机制。
Biochemistry. 2006 Jan 31;45(4):1138-50. doi: 10.1021/bi051966w.
6
Intrinsic isotope effects on benzylic hydroxylation by the aromatic amino acid hydroxylases: evidence for hydrogen tunneling, coupled motion, and similar reactivities.芳香族氨基酸羟化酶对苄基羟基化的内在同位素效应：氢隧穿、耦合运动和相似反应性的证据
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7
Structure of the sodium borohydride-reduced N-(cyclopropyl)glycine adduct of the flavoenzyme monomeric sarcosine oxidase.黄素酶单体肌氨酸氧化酶的硼氢化钠还原型N-（环丙基）甘氨酸加合物的结构
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8
Determination of a large reorganization energy barrier for hydride abstraction by glucose oxidase.葡萄糖氧化酶夺取氢化物的大重组能垒的测定。
J Am Chem Soc. 2005 Nov 16;127(45):15720-1. doi: 10.1021/ja056025l.
9
Crystal structures of Fms1 and its complex with spermine reveal substrate specificity.Fms1及其与精胺复合物的晶体结构揭示了底物特异性。
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10
pH and kinetic isotope effects on sarcosine oxidation by N-methyltryptophan oxidase.pH值和动力学同位素效应对N-甲基色氨酸氧化酶催化肌氨酸氧化的影响。
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从动力学同位素效应洞察黄素蛋白氧化酶的机制

Insights into the mechanisms of flavoprotein oxidases from kinetic isotope effects.

作者信息

Fitzpatrick Paul F

机构信息

Departments of Biochemistry and Biophysics and of Chemistry, Texas A&M University, College Station, TX 77843-2128, USA.

出版信息

J Labelled Comp Radiopharm. 2007 Oct;50(11-12):1016-1025. doi: 10.1002/jlcr.1400.

DOI:10.1002/jlcr.1400
PMID:19890477
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2771875/
Abstract

Deuterium, solvent, and (15)N kinetic isotope effects have been used to probe the mechanisms by which flavoproteins oxidize carbon-oxygen and carbon-nitrogen bonds in amines, hydroxy acids, and alcohols. For the amine oxidases d-amino acid oxidase, N-methyltryptophan oxidase, and tryptophan monooxygenase, d-serine, sarcosine, and alanine are slow substrates for which CH bond cleavage is fully rate limiting. Inverse isotope effects for each of 0.992-0.996 are consistent with a common mechanism involving hydride transfer from the uncharged amine. Computational analyses of possible mechanisms support this conclusion. Deuterium and solvent isotope effects with wild-type and mutant variants of the lactate dehydrogenase flavocytochrome b(2) show that OH and CH bond cleavage are not concerted, but become so in the Y254F enzyme. This is consistent with a highly asynchronous reaction in which OH bond cleavage precedes hydride transfer. The results of Hammett analyses and solvent and deuterium isotope effects support a similar mechanism for alcohol oxidase.

摘要

氘、溶剂和（15）N动力学同位素效应已被用于探究黄素蛋白氧化胺类、羟基酸和醇类中碳 - 氧键和碳 - 氮键的机制。对于胺氧化酶d - 氨基酸氧化酶、N - 甲基色氨酸氧化酶和色氨酸单加氧酶，d - 丝氨酸、肌氨酸和丙氨酸是缓慢的底物，其中C - H键裂解是完全限速步骤。0.992 - 0.996的每个反向同位素效应与涉及从不带电荷的胺转移氢化物的共同机制一致。对可能机制的计算分析支持这一结论。乳酸脱氢酶黄素细胞色素b（2）的野生型和突变体变体的氘和溶剂同位素效应表明，O - H和C - H键裂解不是协同的，但在Y254F酶中变为协同。这与高度异步反应一致，其中O - H键裂解先于氢化物转移。哈米特分析结果以及溶剂和氘同位素效应支持醇氧化酶的类似机制。