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重新利用 Pummerer 重排反应：肽中蛋氨酸砜的测定。

Repurposing the Pummerer Rearrangement: Determination of Methionine Sulfoxides in Peptides.

机构信息

Imaging Probe Development Center, National Heart, Lung and Blood Institute, National Institutes of Health, 9800 Medical Center Drive, Rockville, MD, 20850, USA.

Advanced Biomedical Computational Sciences Group, Frederick National Laboratory for Cancer Research operated by, Leidos Biomedical Research, Inc., 1011 Beasley Drive, Frederick, MD, 21701, USA.

出版信息

Chembiochem. 2020 Feb 17;21(4):508-516. doi: 10.1002/cbic.201900463. Epub 2019 Oct 25.

DOI:10.1002/cbic.201900463
PMID:31365170
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7065062/
Abstract

The reversible oxidation of methionine residues in proteins has emerged as a biologically important post-translational modification. However, detection and quantitation of methionine sulfoxide in proteins is difficult. Our aim is to develop a method for specifically derivatizing methionine sulfoxide residues. We report a Pummerer rearrangement of methionine sulfoxide treated sequentially with trimethylsilyl chloride and then 2-mercaptoimidazole or pyridine-2-thiol to produce a dithioacetal product. This derivative is stable to standard mass spectrometry conditions, and its formation identified oxidized methionine residues. The scope and requirements of dithioacetal formation are reported for methionine sulfoxide and model substrates. The reaction intermediates have been investigated by computational techniques and by C NMR spectroscopy. These provide evidence for an α-chlorinated intermediate. The derivatization allows for detection and quantitation of methionine sulfoxide in proteins by mass spectrometry and potentially by immunochemical methods.

摘要

甲硫氨酸残基在蛋白质中的氧化还原反应已成为一种重要的翻译后修饰。然而，检测和定量蛋白质中的甲硫氨酸亚砜是困难的。我们的目的是开发一种特异性衍生甲硫氨酸亚砜残基的方法。我们报告了一种用三甲基氯硅烷处理甲硫氨酸亚砜，然后用 2-巯基咪唑或吡啶-2-硫醇顺序处理的 Pummerer 重排反应，产生二硫缩醛产物。该衍生物在标准质谱条件下稳定，其形成可鉴定氧化的甲硫氨酸残基。报道了二硫缩醛形成的范围和要求，包括甲硫氨酸亚砜和模型底物。通过计算技术和 C NMR 光谱研究了反应中间体。这些提供了α-氯代中间体的证据。该衍生化允许通过质谱法和潜在的免疫化学方法检测和定量蛋白质中的甲硫氨酸亚砜。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/4f0707956dd4/CBIC-21-508-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/d22699cf35a7/CBIC-21-508-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/587dd93a6eca/CBIC-21-508-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/872146dd5a33/CBIC-21-508-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/d17daf27dbd3/CBIC-21-508-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/4f0707956dd4/CBIC-21-508-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/d22699cf35a7/CBIC-21-508-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/587dd93a6eca/CBIC-21-508-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/872146dd5a33/CBIC-21-508-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/d17daf27dbd3/CBIC-21-508-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/959f/7065062/4f0707956dd4/CBIC-21-508-g002.jpg

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本文引用的文献

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Methionine in Proteins: It's Not Just for Protein Initiation Anymore.蛋白质中的甲硫氨酸：它不再仅仅用于蛋白质起始合成。
Neurochem Res. 2019 Jan;44(1):247-257. doi: 10.1007/s11064-017-2460-0. Epub 2018 Jan 11.
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SelR reverses Mical-mediated oxidation of actin to regulate F-actin dynamics.SelR 逆转 Mical 介导的肌动蛋白氧化，从而调节 F-肌动蛋白的动态变化。
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Proteomics methods to study methionine oxidation.蛋白质组学方法研究蛋氨酸氧化。
Mass Spectrom Rev. 2014 Mar-Apr;33(2):147-56. doi: 10.1002/mas.21386. Epub 2013 Oct 31.
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MsrB1 and MICALs regulate actin assembly and macrophage function via reversible stereoselective methionine oxidation.MsrB1 和 MICALs 通过可逆立体选择性蛋氨酸氧化调节肌动蛋白组装和巨噬细胞功能。
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Wanted and wanting: antibody against methionine sulfoxide.需求与渴望：针对甲硫氨酸砜的抗体。
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