Synthetic Study on Selenocystine-Containing Peptides

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

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64 Citations (Scopus)

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 languageEnglish
Pages (from-to)502-506
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number3
DOIs
Publication statusPublished - 1993 Jan 1
Externally publishedYes

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

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  • Cite this

    Koide, T., Itoh, H., Otaka, A., Yasui, H., Kuroda, M., Fujii, N., Esaki, N., & Soda, K. (1993). Synthetic Study on Selenocystine-Containing Peptides. Chemical and Pharmaceutical Bulletin, 41(3), 502-506. https://doi.org/10.1248/cpb.41.502