Synthetic study of selenocystine-containing peptides

Takaki Koide, H. Itoh, A. Otaka, H. Yasui, M. Kuroda, N. Esaki, K. Soda, N. Fujii

Research output: Contribution to journalArticle

62 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
Publication statusPublished - 1993
Externally publishedYes

Fingerprint

Trifluoroacetic Acid
Peptides
Solid-Phase Synthesis Techniques
Dimethyl Sulfoxide
Iodine
Disulfides
Glutathione
Kinetics
selenocystine
N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Koide, T., Itoh, H., Otaka, A., Yasui, H., Kuroda, M., Esaki, N., ... Fujii, N. (1993). Synthetic study of selenocystine-containing peptides. Chemical and Pharmaceutical Bulletin, 41(3), 502-506.

Synthetic study of selenocystine-containing peptides. / Koide, Takaki; Itoh, H.; Otaka, A.; Yasui, H.; Kuroda, M.; Esaki, N.; Soda, K.; Fujii, N.

In: Chemical and Pharmaceutical Bulletin, Vol. 41, No. 3, 1993, p. 502-506.

Research output: Contribution to journalArticle

Koide, T, Itoh, H, Otaka, A, Yasui, H, Kuroda, M, Esaki, N, Soda, K & Fujii, N 1993, 'Synthetic study of selenocystine-containing peptides', Chemical and Pharmaceutical Bulletin, vol. 41, no. 3, pp. 502-506.
Koide T, Itoh H, Otaka A, Yasui H, Kuroda M, Esaki N et al. Synthetic study of selenocystine-containing peptides. Chemical and Pharmaceutical Bulletin. 1993;41(3):502-506.
Koide, Takaki ; Itoh, H. ; Otaka, A. ; Yasui, H. ; Kuroda, M. ; Esaki, N. ; Soda, K. ; Fujii, N. / Synthetic study of selenocystine-containing peptides. In: Chemical and Pharmaceutical Bulletin. 1993 ; Vol. 41, No. 3. pp. 502-506.
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