Synthetic study of selenocystine-containing peptides

DOI: 10.1248/cpb.41.502

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 502 - 506 (1993)

Update date:2022-08-04

Topics:

Authors:

Koide Koide

Itoh Itoh

Otaka Otaka

Yasui Yasui

Kuroda Kuroda

Esaki Esaki

Soda Soda

Fujii Fujii

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Article abstract of DOI:10.1248/cpb.41.502

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.

Full text of DOI:10.1248/cpb.41.502

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