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.
MeSH terms
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Amino Acid Sequence
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Amino Acids / analysis
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Antiviral Agents / chemistry
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Cystine / analogs & derivatives*
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Cystine / chemistry
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Fluorenes / chemical synthesis
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Fluorenes / chemistry*
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Glutathione / chemistry
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Molecular Sequence Data
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Organoselenium Compounds / chemistry*
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Oxidation-Reduction
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Peptides / chemical synthesis*
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Peptides / chemistry
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Selenocysteine / analogs & derivatives*
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Selenocysteine / chemical synthesis
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Selenocysteine / chemistry
Substances
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Amino Acids
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Antiviral Agents
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Fluorenes
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Organoselenium Compounds
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Peptides
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Selenocysteine
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selenocystine
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N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine
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Cystine
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Glutathione