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以半胱氨酸和赖氨酸侧链为模型体系,研究氧代戊醛与它们反应生成的吡咯交联异构体的结构特征及 pH 值依赖性偏好。

Structural characterisation and pH-dependent preference of pyrrole cross-link isoforms from reactions of oxoenal with cysteine and lysine side chains as model systems.

机构信息

Center for Advanced Technology, Adam Mickiewicz University, Uniwersytetu Poznańskiego 10, 61-614, Poznan, Poland.

Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland.

出版信息

Amino Acids. 2023 Sep;55(9):1073-1082. doi: 10.1007/s00726-023-03295-0. Epub 2023 Jul 11.

Abstract

In this study, we subjected 5,5-diethoxy-4-oxopent-2-enal (DOPE), a model amino acids cross-linking reagent, to reactions with N-acetylcysteine (Ac-Cys) and N-acetyllysine (Ac-Lys), and identified three pyrrole cross-links. The compounds were isolated and their structures were rigorously determined by spectrometric and spectroscopic methods, including 2D NMR experiments. The use of 2D NMR spectroscopy was crucial to determine the position of the substituents in the pyrrole rings. The products were identified as 2,4-, 2,3-, and 2,5-substituted pyrroles. The data obtained from their structural characterisation can help similar studies on amino acids modifications induced by analogous bifunctional carbonyl compounds. Our results show that the study of pathways in which model electrophiles modify amino acids may be helpful for similar studies dealing with identification of structural changes in cysteine- and lysine-containing proteins associated with oxidative stress.

摘要

在这项研究中,我们将 5,5-二乙氧基-4-氧代戊-2-烯醛(DOPE),一种模型氨基酸交联试剂,与 N-乙酰半胱氨酸(Ac-Cys)和 N-乙酰赖氨酸(Ac-Lys)进行反应,鉴定出三种吡咯交联物。通过光谱和光谱学方法,包括 2D NMR 实验,对化合物进行了分离和结构的严格确定。2D NMR 光谱学的使用对于确定吡咯环中取代基的位置至关重要。鉴定出的产物为 2,4-、2,3-和 2,5-取代的吡咯。从其结构特征获得的数据可以帮助类似的研究,研究类似的双官能羰基化合物诱导的氨基酸修饰。我们的结果表明,研究模型亲电试剂修饰氨基酸的途径可能有助于类似的研究,鉴定与氧化应激相关的含半胱氨酸和赖氨酸的蛋白质中的结构变化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbe5/10564825/8e2260ec352c/726_2023_3295_Sch1_HTML.jpg

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