Aliphatic amino acid side chains associatewith the “face” of the adenine ring

Academic Article


  • We have synthesized the free amino acid adenylate anydrides of phenylalanine, leucine, isoleucine and valine. These activated compounds are very labile at high pH, but at low pH they become more stable. Proton NMR spectra of these adenylates show that, in every case, the hydrophobic side chains, even in these small molecules at low pH and low concentration, are associated with the “face” of the adenine ring. Although aromatic rings are known to associate with adenine in this fashion, to our knowledge this is the first report of an intercalative-type interaction of aliphatic side chains with nucleic acid bases. Since adenine is the most hydrophobic base, these interactions are of a hydrophobic character, and occur in spite of the fact that the adenine ring is protonated. These results may have implications regarding recognition processes in DNA-protein and RNA-protein interactions. © 1986 Taylor & Francis Group, LLC.
  • Digital Object Identifier (doi)

    Author List

  • Lacey JC; Mullins DW; Watkins CL
  • Start Page

  • 783
  • End Page

  • 794
  • Volume

  • 3