Investigation of the dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis of cystine-containing peptides.
Disulfide bonds of peptides were effectively established between S-protected cysteine residues as well as free cysteine residues by the action of dimethylsulfoxide in trifluoroacetic acid. Oxytocin and alpha-human calcitonin gene-related peptide were synthesized using this oxidation system. The feasibility of this method for the formation of two disulfide bridges of apamin was also examined.
Koide
T
T
Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Otaka
A
A
Fujii
N
N
D000595:Amino Acid Sequence; D001030:Apamin / Q000138:chemical synthesis* / Q000737:chemistry; D015740:Calcitonin Gene-Related Peptide / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003553:Cystine / Q000032:analysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry; D006801:Humans; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010121:Oxytocin / Q000138:chemical synthesis* / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D004220:Disulfides; D001030:Apamin; D003553:Cystine; D010121:Oxytocin; D014269:Trifluoroacetic Acid; D015740:Calcitonin Gene-Related Peptide; D004121:Dimethyl Sulfoxide