Dehydration promotes phosphoramidate-linked amino acidyl and peptido adenosine conjugates

Chem Commun (Camb). 2024 Oct 15;60(83):11920-11923. doi: 10.1039/d4cc03602f.

Abstract

Cyclic nucleoside phosphates have been shown previously to be adequately activated to oligomerise under dry conditions. Herein, it is demonstrated that 3',5'-cyclic adenosine monophosphate (3',5'-cAMP) and glycine when subjected to dehydration under alkaline conditions form phosphoramidate-linked conjugates. Solid-state reaction mechanisms investigated by DFT suggest why the reaction does not occur efficiently in the aqueous phase.

MeSH terms

  • Adenosine / chemistry
  • Amides* / chemistry
  • Amino Acids / chemistry
  • Dehydration
  • Density Functional Theory
  • Glycine / analogs & derivatives
  • Glycine / chemistry
  • Molecular Structure
  • Phosphoric Acids* / chemistry
  • Water / chemistry

Substances

  • phosphoramidic acid
  • Phosphoric Acids
  • Amides
  • Adenosine
  • Water
  • Glycine
  • Amino Acids