Abstract
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.
Original language | English |
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Pages (from-to) | 502-506 |
Number of pages | 5 |
Journal | Chemical and Pharmaceutical Bulletin |
Volume | 41 |
Issue number | 3 |
DOIs | |
Publication status | Published - 1993 |
Externally published | Yes |
Keywords
- Fmoc-based solid-phase peptide synthesis
- N-9-fluorenylmethoxycarbonyl-Se-methoxybenzylselenocysteine
- diselenide bond formation
- disulfide bond formation
- selenocysteine
- selenocystine
ASJC Scopus subject areas
- Chemistry(all)
- Drug Discovery