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- 烷基谷胱甘肽的单电子氧化生成的α-氨基酸烷基自由基的意外反应途径。

Unexpected Reaction Pathway of the Alpha-Aminoalkyl Radical Derived from One-Electron Oxidation of -Alkylglutathiones.

机构信息

Faculty of Chemistry, Adam Mickiewicz University, 61-614 Poznan, Poland.

Center for Advanced Technology, Adam Mickiewicz University, 61-614 Poznan, Poland.

出版信息

Molecules. 2020 Feb 17;25(4):877. doi: 10.3390/molecules25040877.

DOI:10.3390/molecules25040877
PMID:32079230
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7070667/
Abstract

Laser flash photolysis and high-resolution mass spectrometry were used to investigate the mechanism of one-electron oxidation of two -alkylglutathiones using 3-carboxybenzophenone (3CB) as a photosensitizer. This report indicates an unexpected reaction pathway of the α-aminoalkyl radical cation (αN) derived from the oxidation of -alkylglutathiones. Instead of a common hydrolysis reaction of αN reported earlier for methionine and other sulfur-containing aminoacids and peptides, an intramolecular ring-closure reaction was found for -alkylglutathiones.

摘要

激光闪光光解和高分辨率质谱联用技术被用于研究使用 3-羧基二苯甲酮(3CB)作为光敏剂的二烷基谷胱甘肽的单电子氧化反应机制。该报告指出了来自于二烷基谷胱甘肽氧化的α-氨烷基自由基阳离子(αN)的一个意想不到的反应途径。与之前报道的甲硫氨酸和其他含硫氨基酸和肽的αN的常见水解反应不同,对于二烷基谷胱甘肽发现了分子内环合反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/258e5e8d0bb1/molecules-25-00877-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/b832c3d54aff/molecules-25-00877-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/e419ced344f4/molecules-25-00877-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/c811e24b0e07/molecules-25-00877-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/95e20871bfee/molecules-25-00877-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/cb15088f7a3c/molecules-25-00877-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/fc4c2394605c/molecules-25-00877-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/258e5e8d0bb1/molecules-25-00877-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/b832c3d54aff/molecules-25-00877-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/e419ced344f4/molecules-25-00877-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/c811e24b0e07/molecules-25-00877-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/95e20871bfee/molecules-25-00877-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/cb15088f7a3c/molecules-25-00877-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/fc4c2394605c/molecules-25-00877-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8442/7070667/258e5e8d0bb1/molecules-25-00877-g006.jpg

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本文引用的文献

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Formation of a Three-Electron Sulfur-Sulfur Bond as a Probe for Interaction between Side Chains of Methionine Residues.形成三电子硫-硫键作为甲硫氨酸残基侧链间相互作用的探针。
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J Phys Chem B. 2014 Jul 24;118(29):8549-58. doi: 10.1021/jp5039305. Epub 2014 Jul 2.
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[Protective action of ethylglutathione at hypoxia-reoxygenation of the heart: role of glucose].[乙基谷胱甘肽在心脏缺氧复氧中的保护作用:葡萄糖的作用]
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