Synthetic study on selenocystine-containing peptides.
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.
Koide
T
T
Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Itoh
H
H
Otaka
A
A
Yasui
H
H
Kuroda
M
M
Esaki
N
N
Soda
K
K
Fujii
N
N
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis; D000998:Antiviral Agents / Q000737:chemistry; D003553:Cystine / Q000031:analogs & derivatives* / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D005978:Glutathione / Q000737:chemistry; D008969:Molecular Sequence Data; D016566:Organoselenium Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017279:Selenocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000596:Amino Acids; D000998:Antiviral Agents; D005449:Fluorenes; D016566:Organoselenium Compounds; D010455:Peptides; D017279:Selenocysteine; C009226:selenocystine; C080912:N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine; D003553:Cystine; D005978:Glutathione