Synthesis of nucleoside N-phosphoamino acids and peptide formation.
Nucleoside N-phosphoamino acids were synthesized through Atherton-Todd reaction of nucleoside H-phosphonate with amino acids, and their structures were confirmed by NMR and ESI-MS. After nucleoside N-phosphoamino acid was incubated in anhydrous methanol at 40 degrees C for 72 h, di- to tetra-peptide derivatives were detected by ESI-MS, and their structures were further identified by multistage mass spectrometry. These and previously published studies in aqueous solution suggest that nucleoside N-phosphoamino acids could have been prebiotic precursors of oligopeptides.
Lin
Changxue
C
The Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, P R China.
Fu
Hua
H
Zhao
Yufen
Y
Cheng
Changmei
C
D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D019606:Phosphoamino Acids / Q000737:chemistry*; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water
D009705:Nucleosides; D009842:Oligopeptides; D019606:Phosphoamino Acids; D012996:Solutions; D014867:Water