Koide T, Itoh H, Otaka A, Yasui H, Kuroda M, Esaki N, Soda K, Fujii N
Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Chem Pharm Bull (Tokyo). 1993 Mar;41(3):502-6. doi: 10.1248/cpb.41.502.
N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine++ + [Fmoc-Sec(MBzl)-OH] was synthesized from selenocystine and successfully applied to Fmoc-based solid-phase peptide synthesis. The stability and the deprotection conditions of the Se-MBzl group were examined. The diselenide bond of a peptide was directly and effectively established between Sec(MBzl) residues by treatment with iodine or the dimethyl sulfoxide-trifluoroacetic acid system. Reduction kinetics of diselenide and disulfide in model peptides by reduced glutathione were also studied comparatively.
N-9-芴甲氧羰基-Se-4-甲氧基苄基硒代半胱氨酸[Fmoc-Sec(MBzl)-OH]由硒代胱氨酸合成，并成功应用于基于Fmoc的固相肽合成。考察了Se-MBzl基团的稳定性和脱保护条件。通过用碘或二甲基亚砜-三氟乙酸体系处理，在Sec(MBzl)残基之间直接有效地形成了肽的二硒键。还比较研究了还原型谷胱甘肽对模型肽中二硒键和二硫键的还原动力学。
