Hydrogen peroxide for disulfide bridge formation in methionine-containing peptides.
Two methionine-containing peptides, endothelin 1 and the 1-16 fragment of the receptor of the plasminogen activator 1 for human urokinase, were synthesized and cyclized by hydrogen peroxide. Endothelin 1 was obtained by using regioselective and random schemes of disulfide bond formation. The conditions of cyclization that provided the target products in high purity were found. The general potential of disulfide bond formation by means of hydrogen peroxide was demonstrated for methionine-containing peptides. The method resulted in target products containing insignificant quantities of the corresponding Met-sulfoxide derivatives.
Kudryavtseva
E V
EV
Peptide Synthesis Ltd., Moscow, Russian Federation. peptide@cardio.ru
Sidorova
M V
MV
Ovchinnikov
M V
MV
Bespalova
Z D
ZD
D000595:Amino Acid Sequence; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004220:Disulfides; D004285:Dogs; D019332:Endothelin-1 / Q000138:chemical synthesis*; D006801:Humans; D006861:Hydrogen Peroxide / Q000494:pharmacology*; D006863:Hydrogen-Ion Concentration; D013058:Mass Spectrometry; D008715:Methionine / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D051381:Rats; D011956:Receptors, Cell Surface / Q000737:chemistry*; D055293:Receptors, Urokinase Plasminogen Activator; D013552:Swine
D004220:Disulfides; D019332:Endothelin-1; C524898:PLAUR protein, human; D010455:Peptides; C524900:Plaur protein, rat; D011956:Receptors, Cell Surface; D055293:Receptors, Urokinase Plasminogen Activator; D008715:Methionine; D006861:Hydrogen Peroxide