College of Chemistry and Environmental Science, Key Laboratory of Analytical Science and Technology of Hebei Province, and MOE Key Laboratory of Medicinal Chemistry and Molecular Diagnostics, Hebei University, Baoding 071002, Hebei Province, P. R. China.
J Org Chem. 2021 Mar 5;86(5):4035-4044. doi: 10.1021/acs.joc.0c02877. Epub 2021 Feb 23.
In this study, l-methionine selenoxide (MetSeO) was used as an oxidant for the construction of peptide disulfide bonds. Excellent yields for various disulfide-containing peptides were achieved the MetSeO oxidation method in different solvents and on a resin. Most importantly, the construction of disulfide bonds can be performed in the trifluoroacetic acid cocktail used for the cleavage of peptides from the resin, which obviates the steps of peptide purification and lyophilization. This facilitates and simplifies the synthesis of disulfide-containing peptides. Kinetic and mechanistic studies of the reaction between MetSeO and dithiothreitol (DTT, a model compound of dicysteine-containing peptide) show that the reaction is first order in both [MetSeO] and [DTT], and a reaction mechanism is proposed that can help us gain insights into the reaction of the oxidative synthesis of disulfide bonds MetSeO oxidation.
在这项研究中，L-甲硫氨酸亚硒氧化物（MetSeO）被用作构建肽中二硫键的氧化剂。在不同溶剂中和树脂上，该方法都能以优异的收率得到各种含二硫键的肽。最重要的是，二硫键的构建可以在用于从树脂上切割肽的三氟乙酸混合液中进行，从而省去了肽的纯化和冻干步骤。这使得含二硫键的肽的合成更加简便。MetSeO 与二硫苏糖醇（DTT，二半胱氨酸肽的模型化合物）之间反应的动力学和机理研究表明，该反应在[MetSeO]和[DTT]中均为一级反应，并提出了一种反应机理，有助于我们深入了解 MetSeO 氧化的二硫键氧化合成反应。
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