Small-molecule models of tyrosinase: From ligand hydroxylation to catalytic monooxygenation of external substrates

Hamann Jessica Nadine; Herzigkeit Benjamin; Jurgeleit Ramona; Tuczek Felix

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Small-molecule models of tyrosinase: From ligand hydroxylation to catalytic monooxygenation of external substrates

机译：酪氨酸酶的小分子模型：从配体羟基化到外部底物的催化单加氧

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The reactivities of tyrosinase and catechol oxidase have been of continued interest during the last decades. To gain mechanistic insights into the conversion of mono- and diphenols by these type 3 copper enzymes, a large range of model systems has been developed. This review describes our newest results in this field. Our approach involves with the synthesis of mono- and dinucleating ligands based on imine and/or different heterocyclic groups. The influence of the ligand framework on the catalytic conversion of external substrates is investigated. Besides catalytic systems we also investigated new dicopper complexes exhibiting ligand hydroxylation reactions. The implications of these results on the mechanism of tyrosinase and catechol oxidase are discussed. (C) 2016 Elsevier B.V. All rights reserved.

机译：在过去的几十年中，人们一直对酪氨酸酶和儿茶酚氧化酶的反应性感兴趣。为了获得有关这些3型铜酶转化单酚和二酚的机理的见解，已经开发了许多模型系统。这篇评论描述了我们在该领域的最新结果。我们的方法涉及基于亚胺和/或不同杂环基团的单核和双核配体的合成。研究了配体骨架对外部底物催化转化的影响。除催化系统外，我们还研究了表现出配体羟基化反应的新型双铜配合物。讨论了这些结果对酪氨酸酶和儿茶酚氧化酶机制的影响。（C）2016 Elsevier B.V.保留所有权利。

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来源
《Coordination chemistry reviews》 |2017年第3期|54-66|共13页
作者
Hamann Jessica Nadine; Herzigkeit Benjamin; Jurgeleit Ramona; Tuczek Felix;
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作者单位

Christian Albrechts Univ Kiel, Inst Inorgan Chem, Max Eyth Str 2, D-24118 Kiel, Germany;

Christian Albrechts Univ Kiel, Inst Inorgan Chem, Max Eyth Str 2, D-24118 Kiel, Germany;

Christian Albrechts Univ Kiel, Inst Inorgan Chem, Max Eyth Str 2, D-24118 Kiel, Germany;

Christian Albrechts Univ Kiel, Inst Inorgan Chem, Max Eyth Str 2, D-24118 Kiel, Germany;

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收录信息美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);
原文格式 PDF
正文语种 eng
中图分类
关键词
Type 3 copper enzymes; Tyrosinase; Catechol oxidase; Model systems; Dioxygen activation;

机译：3型铜酶;酪氨酸酶;儿茶酚氧化酶;模型系统;双氧激活;

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专利

1. Monooxygenation of external phenolic substrates in small-molecule dicopper complexes: implications on the reaction mechanism of tyrosinase [J] . Rolff M, Schottenheim J, Tuczek F Journal of Coordination Chemistry . 2010,第14a16期

机译：小分子双铜配合物中外部酚类底物的单加氧作用：对酪氨酸酶反应机理的影响
2. Modeling tyrosinase activity. Effect of ligand topology on aromatic ring hydroxylation: An overview [J] . De A, Mandal S, Mukherjee R Journal of Inorganic Biochemistry: An Interdisciplinary Journal . 2008,第5a6期

机译：模拟酪氨酸酶活性。配体拓扑结构对芳环羟基化的影响：概述
3. Modeling tyrosinase monooxygenase activity. Spectroscopic and magnetic investigations of products due to reactions between copper(I) complexes of xylyl-based dinucleating ligands and dioxygen: Aromatic ring hydroxylations and irreversible oxidation p [J] . Ghosh D., Mukherjee R. Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics . 1999,第4期

机译：模拟酪氨酸酶单加氧酶活性。由于基于二甲苯基的双核配体的铜（I）配合物与双氧之间的反应而引起的产物的光谱和磁学研究：芳香环羟基化和不可逆氧化p
4. The Optimization of the Bio-Panning Process of the Affinity Ligand of Tyrosinase by Phage Display Technology [C] . Wang Wen, Nie Hua-Li, Chen Tian-Xiang, 5th International Conference on Bioinformatics and Biomedical Engineering . 2011

机译：噬菌体展示技术优化酪氨酸酶亲和配体的生物标记工艺
5. An efficient catalytic oxygenation of hydrocarbons using iodosobenzene diacetate-metalloporphyrin systems as oxidants: A model for cytochrome P-450 monooxygenation enzyme [D] . Mirafzal, Gholam Abbass 1991

机译：使用碘代苯二乙酸盐-金属卟啉体系作为氧化剂的碳氢化合物有效催化氧化：细胞色素P-450单加氧酶的模型
6. Catalytic Phenol Hydroxylation with Dioxygen: Extension of the Tyrosinase Mechanism Beyond the Protein Matrix [O] . Alexander Hoffmann, Cooper Citek, Stephan Binder, -1

机译：双氧催化苯酚羟基化：超越蛋白质基质的酪氨酸酶机制的扩展。
7. New catalytic model systems of tyrosinase: fine tuning of the reactivity with pyrazole-based N-donor ligands [O] . Jessica Nadine Hamann, Felix Tuczek 2014

机译：酪氨酸酶新的催化模型系统：与吡唑基N-供体配体的反应性微调

Small-molecule models of tyrosinase: From ligand hydroxylation to catalytic monooxygenation of external substrates

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