Regioselective formation, using orthogonal cysteine protection, of an alpha-conotoxin dimer peptide containing four disulfide bonds.
[structure: see text] The combination of the cysteine thiol protecting groups Trt, Acm, tBu, and MeBzl were used for the regioselective formation of an alpha-conotoxin dimer peptide containing four disulfide bridges. Additionally, a protocol is described whereby two one-pot oxidations were employed in order to improve the efficiency of the folding process. The target compound was produced in good yield.
Cuthbertson
Alan
A
Amersham Health AS, Department of Medicinal Chemistry, Oslo, Norway. alan.cuthbertson@amersham.com
Indrevoll
Bård
B
D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D020916:Conotoxins / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D019281:Dimerization; D004220:Disulfides / Q000737:chemistry*; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction
D020916:Conotoxins; D004220:Disulfides; D003545:Cysteine