Synthesis of peptide thioacids at neutral pH using bis(2-sulfanylethyl)amido peptide precursors.
Reaction of bis(2-sulfanylethyl)amido (SEA) peptides with triisopropylsilylthiol in water at neutral pH yields peptide thiocarboxylates. An alkylthioester derived from β-alanine was used to trap the released bis(2-sulfanylethyl)amine and displace the equilibrium toward the peptide thiocarboxylate.
UMR CNRS 8161, Pasteur Institute of Lille 59021 Lille, France.
Silvain L
SL
Pira
Emmanuelle
E
Boll
Oleg
O
Melnyk
D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D002264:Carboxylic Acids; D010455:Peptides; D013438:Sulfhydryl Compounds