Interaction between N-phosphoryl-α-, β- and γ-amino acids and nucleosides

The reactions of four different N-(O,O′-diisopropyl) phosphoamino acids (DIPP-aa), such as N-phosphoryl-l-α-alanine (DIPP-l-α-Ala), N-phosphoryl-d-α-alanine (DIPP-d-α-Ala), N-phosphoryl-β-alanine (DIPP-β-Ala) and N-phosphoryl-γ-amino butyric acid (DIPP-γ-Aba), and four nucleosides, adenosine (A), guanosine (G), cytidine (C) and uridine (U), were studied by electrospray ionization tandem mass spectrometry (ESI-MS/MS) and HPLC/ESI-MS. DIPP-l-α-Ala and DIPP-d-α-Ala produced the same phosphorylated nucleosides, dinucleotides and phosphoroligopeptide. However, DIPP-β-Ala and DIPP-γ-Aba gave no relevant products.