title: Side reactions in peptide synthesis. X. Prevention of O-acylation during coupling with active esters.
abstract: Acylation of the hydroxyl groups in the side chains of serine, threonine or tyrosine occurs in coupling with active esters. This side reaction, which is quite pronounced in histidine-containing peptides, can be prevented with additives. From a series of compounds tested, 2,4-dinitrophenol and pentachlorophenol were the most effective.
mesh_terms: D000215:Acylation; D000595:Amino Acid Sequence; D004140:Dinitrophenols; D004952:Esters; D010416:Pentachlorophenol; D010455:Peptides / Q000138:chemical synthesis*; D012694:Serine; D013912:Threonine; D014443:Tyrosine
chemical_list: D004140:Dinitrophenols; D004952:Esters; D010455:Peptides; D013912:Threonine; D014443:Tyrosine; D012694:Serine; D010416:Pentachlorophenol