Phosphoryl group participation leads to peptide formation from N-phosphorylamino acids.
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.
Li
Y M
YM
Department of Chemistry, Tsinghua University, Beijing, P.R. China.
Yin
Y W
YW
Zhao
Y F
YF
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
D000596:Amino Acids; D010455:Peptides