How formaldehyde reacts with amino acids
How formaldehyde reacts with amino acids
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DOI：
10.1038/s42004-019-0224-2
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发表时间：
2019-11-07
影响因子：
5.9
通讯作者：
Claridge, Timothy D. W.
中科院分区：
文献类型：
--
作者：
Kamps, Jos J. A. G.;Hopkinson, Richard J.;Claridge, Timothy D. W.
甲醛是通过包括酶促脱甲基化的过程产生的生物亲电试剂。尽管甲醛与基本生物成分的反应看起来很简单，但它并没有完全被定义。在这里，我们报告基于核磁共振研究甲醛与常见的蛋白质和其他亲核氨基酸的反应。结果表明，甲醛以不同的速率反应，形成不同稳定性的羟甲基化，环化，交联或交联产物。在测试的常见氨基酸中，半胱氨酸反应最有效，形成稳定的噻唑烷。与赖氨酸的反应效率较低;观察到低水平的Ne-甲基化产物，提高了甲醛非酶促赖氨酸甲基化的可能性。与甲醛的反应比与其他测试的生物羰基化合物的反应更快，并且加合物也更稳定。结果显示，甲醛与氨基酸的反应，以及延伸的肽和蛋白质，在健康和疾病生物学以及进化中具有潜在的作用。
Formaldehyde is a biological electrophile produced via processes including enzymatic demethylation. Despite its apparent simplicity, the reactions of formaldehyde with even basic biological components are incompletely defined. Here we report NMR-based studies on the reactions of formaldehyde with common proteinogenic and other nucleophilic amino acids. The results reveal formaldehyde reacts at different rates, forming hydroxymethylated, cyclised, cross-linked, or disproportionated products of varying stabilities. Of the tested common amino acids, cysteine reacts most efficiently, forming a stable thiazolidine. The reaction with lysine is less efficient; low levels of an Ne-methylated product are observed, raising the possibility of non-enzymatic lysine methylation by formaldehyde. Reactions with formaldehyde are faster than reactions with other tested biological carbonyl compounds, and the adducts are also more stable. The results reveal reactions of formaldehyde with amino acids, and by extension peptides and proteins, have potential roles in healthy and diseased biology, as well as in evolution.