Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400076, India.
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN, 47907, USA.
Amino Acids. 2019 Apr;51(4):661-667. doi: 10.1007/s00726-019-02698-2. Epub 2019 Feb 23.
Selenocysteine (Sec) residue cannot be directly attached to a peptide sequence unless the selenol form is protected beforehand and several problems have been reported in the preparation of Sec building blocks. In this article a series of selenocystine, the oxidized form of Sec, containing peptides has been synthesized using a new methodology, where Boc-NH-chloroalanine is coupled with methyl ester protected residues (Ala, Met, Phe) using DCC/HOBt as the coupling reagents providing di- and tripeptides. Further, the treatment of disodium diselenide with chloroalanine peptides (Boc-ClAla-Ala-OMe, Boc-ClAla-Met-OMe and Boc-ClAla-Ala-Phe-OMe) afforded the respective selenocystine-containing peptides (Boc-Sec-Ala-OMe, Boc-Sec-Met-OMe and Boc-Sec-Ala-Phe-OMe).
硒代半胱氨酸（Sec）残基不能直接连接到肽序列上，除非先保护其硒醇形式，并且在制备 Sec 砌块时已经报道了几个问题。在本文中，使用一种新方法合成了一系列含有硒代胱氨酸（Sec 的氧化形式）的肽，其中 Boc-NH-氯丙氨酸使用 DCC/HOBt 作为偶联试剂与甲酯保护的残基（Ala、Met、Phe）偶联，提供二肽和三肽。此外，用二硒化二钠处理氯丙氨酸肽（Boc-ClAla-Ala-OME、Boc-ClAla-Met-OME 和 Boc-ClAla-Ala-Phe-OME），得到相应的含有硒代胱氨酸的肽（Boc-Sec-Ala-OME、Boc-Sec-Met-OME 和 Boc-Sec-Ala-Phe-OME）。
