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通过模拟酪氨酸羟化酶将酪醇转化为羟基酪醇的仿生合成。

Biomimetic synthesis of hydroxytyrosol from conversion of tyrosol by mimicking tyrosine hydroxylase.

机构信息

Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu, 610065, China.

出版信息

J Biol Inorg Chem. 2023 Jun;28(4):379-391. doi: 10.1007/s00775-023-01996-1. Epub 2023 Apr 5.

DOI:10.1007/s00775-023-01996-1
PMID:37017773
Abstract

Hydroxytyrosol, one of the most powerful natural antioxidants, exhibits certificated benefits for human health. In this study, a biomimetic approach to synthesize hydroxytyrosol from the hydroxylation of tyrosol was established. EDTA-Fe coordination complex served as an active center to simulate tyrosine hydroxylase. HO and ascorbic acid were used as oxygen donor and hydrogen donor, respectively. Hydroxy radical and singlet oxygen contributed to active species. The biomimetic system displayed analogous component, structure, and activity with TyrH. Hydroxytyrosol titer of 21.59 mM, and productivity of 9985.92 mg·L·h was achieved with 100 mM tyrosol as substrate. The proposed approach provided efficient and convenient route to quickly produce high amount of hydroxytyrosol.

摘要

羟基酪醇是一种最强大的天然抗氧化剂,已被证实对人体健康有益。在本研究中,建立了一种从酪氨酸羟化合成羟基酪醇的仿生方法。EDTA-Fe 配合物作为活性中心模拟酪氨酸羟化酶。HO 和抗坏血酸分别作为氧供体和氢供体。羟自由基和单线态氧作为活性物质。仿生体系与 TyrH 具有相似的组成、结构和活性。以 100mM 酪氨酸为底物,可获得 21.59mM 的羟基酪醇浓度和 9985.92mg·L·h 的产率。该方法为快速大量生产羟基酪醇提供了有效便捷的途径。

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1
Biomimetic synthesis of hydroxytyrosol from conversion of tyrosol by mimicking tyrosine hydroxylase.通过模拟酪氨酸羟化酶将酪醇转化为羟基酪醇的仿生合成。
J Biol Inorg Chem. 2023 Jun;28(4):379-391. doi: 10.1007/s00775-023-01996-1. Epub 2023 Apr 5.
2
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本文引用的文献

1
Biomimetic synthesis of L-DOPA inspired by tyrosine hydroxylase.受酪氨酸羟化酶启发的 L-DOPA 的仿生合成。
J Inorg Biochem. 2022 Sep;234:111878. doi: 10.1016/j.jinorgbio.2022.111878. Epub 2022 May 29.
2
Production of biologically active hydroxytyrosol rich extract catalytic conversion of tyrosol.富含生物活性羟基酪醇提取物的生产——酪醇的催化转化
RSC Adv. 2022 Jan 19;12(5):2595-2602. doi: 10.1039/d1ra08875k. eCollection 2022 Jan 18.
3
The role of hydroxylation on·OH generation for enhanced ozonation of benzoic acids: Reactivity, ozonation efficiency and radical formation mechanism.
羟基化对苯甲酸增强臭氧化过程中·OH生成的作用:反应活性、臭氧化效率及自由基形成机制
J Hazard Mater. 2022 Jun 5;431:128620. doi: 10.1016/j.jhazmat.2022.128620. Epub 2022 Mar 4.
4
A coupled enzymatic reaction of tyrosinase and glucose dehydrogenase for the production of hydroxytyrosol.酪氨酸酶和葡萄糖脱氢酶偶联反应生产羟基酪醇。
Appl Microbiol Biotechnol. 2020 Jun;104(11):4945-4955. doi: 10.1007/s00253-020-10594-z. Epub 2020 Apr 13.
5
Developing a highly efficient hydroxytyrosol whole-cell catalyst by de-bottlenecking rate-limiting steps.通过消除限速步骤开发高效的羟基酪醇全细胞催化剂。
Nat Commun. 2020 Mar 23;11(1):1515. doi: 10.1038/s41467-020-14918-5.
6
Chemical, physical and biotechnological approaches to the production of the potent antioxidant hydroxytyrosol.化学、物理和生物技术方法生产强效抗氧化剂羟基酪醇。
Appl Microbiol Biotechnol. 2019 Aug;103(15):5957-5974. doi: 10.1007/s00253-019-09914-9. Epub 2019 Jun 8.
7
Promiscuous enzymatic activity-aided multiple-pathway network design for metabolic flux rearrangement in hydroxytyrosol biosynthesis.灵活的酶学活性辅助的多途径网络设计用于羟基酪醇生物合成中的代谢通量重排。
Nat Commun. 2019 Feb 27;10(1):960. doi: 10.1038/s41467-019-08781-2.
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Effect of Selected Plant Phenolics on Fe-EDTA-H₂O₂ System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions.所选植物酚类物质对Fe-EDTA-H₂O₂体系介导的脱氧核糖氧化的影响:基于分子结构的抗氧化与促氧化作用关系
Molecules. 2016 Dec 31;22(1):59. doi: 10.3390/molecules22010059.
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Biomimetic and Bioinspired Synthesis of Nanomaterials/Nanostructures.纳米材料/纳米结构的仿生与受生物启发合成
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