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 | |
| Publication status | Published - 1993 Jan 1 |
| 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
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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