Synthetic Study on Selenocystine-Containing Peptides

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

doi:10.1248/cpb.41.502

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 journal › Article › peer-review

65 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 language	English
Pages (from-to)	502-506
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	41
Issue number	3
DOIs	https://doi.org/10.1248/cpb.41.502
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

Access to Document

10.1248/cpb.41.502

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title = "Synthetic Study on Selenocystine-Containing Peptides",

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.",

keywords = "Fmoc-based solid-phase peptide synthesis, N-9-fluorenylmethoxycarbonyl-Se-methoxybenzylselenocysteine, diselenide bond formation, disulfide bond formation, selenocysteine, selenocystine",

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

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T1 - Synthetic Study on Selenocystine-Containing Peptides

AU - Koide, Takaki

AU - Itoh, Hiromi

AU - Otaka, Akira

AU - Yasui, Hiroyuki

AU - Kuroda, Masataka

AU - Fujii, Nobutaka

AU - Esaki, Nobuyoshi

AU - Soda, Kenji

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

KW - Fmoc-based solid-phase peptide synthesis

KW - N-9-fluorenylmethoxycarbonyl-Se-methoxybenzylselenocysteine

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KW - disulfide bond formation

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KW - selenocystine

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