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Synthesis of selenopeptides: an alternative way of incorporating selenocystine.
Amino Acids ( IF 3.0 ) Pub Date : 2019-02-23 , DOI: 10.1007/s00726-019-02698-2
Selvaraj Aravindhan 1 , Harkesh B Singh 1 , Matthias Zeller 2 , Ray J Butcher 3
Affiliation  

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).

中文翻译:

硒肽的合成:并入硒代胱氨酸的另一种方法。

除非事先保护硒醇形式,并且在制备Sec结构单元中已报道了几个问题,否则硒代半胱氨酸(Sec)残基不能直接与肽序列相连。在本文中,已使用一种新方法合成了一系列硒代半胱氨酸(Sec的氧化形式),这些肽含有肽,其中Boc-NH-氯丙氨酸与甲酯保护的残基(Ala,Met,Phe)结合使用DCC / HOBt作为提供二肽和三肽的偶联剂。此外,用氯丙氨酸肽(Boc-ClAla-Ala-OMe,Boc-ClAla-Met-OMe和Boc-ClAla-Ala-Phe-OMe)处理二硒化二钠可分别得到含硒代半胱氨酸的肽(Boc-Sec-Ala -OMe,Boc-Sec-Met-OMe和Boc-Sec-Ala-Phe-OMe)。
更新日期:2019-02-23
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