Synthetic Study on Selenocystine-Containing Peptides

Takaki Koide, Hiromi Itoh, Akira Otaka, Hiroyuki Yasui, Masataka Kuroda, Nobutaka Fujii, Nobuyoshi Esaki, Kenji Soda

Research output: Contribution to journalArticlepeer-review

79 Citations (Scopus)


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 languageEnglish
Pages (from-to)502-506
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Issue number3
Publication statusPublished - 1993
Externally publishedYes


  • Fmoc-based solid-phase peptide synthesis
  • N-9-fluorenylmethoxycarbonyl-Se-methoxybenzylselenocysteine
  • diselenide bond formation
  • disulfide bond formation
  • selenocysteine
  • selenocystine

ASJC Scopus subject areas

  • General Chemistry
  • Drug Discovery


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