title: Phosphoryl group participation leads to peptide formation from N-phosphorylamino acids.
abstract: N-phosphorylated amino acids without a side chain functional group can transfer themselves into peptides after prolonged standing in solvents at warm temperatures. Seven N-phosphorylpeptides and free peptides were isolated and their structures determined. The phosphoryl group participation is the key to the peptide formation. An intramolecular mixed carboxylic-phosphoric anhydride intermediate was proposed for this type of reaction which might provide a clue to the function of the phosphoryl group in the phosphorylated enzymes and in the prebiotic synthesis of protein.
authors.affiliation: Department of Chemistry, Tsinghua University, Beijing, P.R. China.
authors.forename: Y M
authors.initials: YM
authors.lastname: Li
authors.forename: Y W
authors.initials: YW
authors.lastname: Yin
authors.forename: Y F
authors.initials: YF
authors.lastname: Zhao
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D010766:Phosphorylation; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: D000596:Amino Acids; D010455:Peptides