lin-benzoadenine nucleotides. Inter- and intramolecular interactions in aqueous solutions as observed by proton magnetic resonance

Jorge R. Barrio, Fu-Tong Liu, Gene E. Keyser, Pieter VanDerLijn, Nelson J. Leonard

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

The inter- and intramolecular interactions of lin-benzoadenine nucleotides have been examined by proton magnetic resonance. When the base is unprotonated, lin-benzoadenine nucleotides strongly stack in aqueous solution, with association constants of at least one order of magnitude greater than those of the corresponding adenine nucleotides. Some head-to-tail orientations of stacked lin-benzoadenine nucleotides were indicated by the deuterium substitution effect on relaxation times (DESERT). The relative positions of the heteroaromatic proton chemical shifts at infinite dilution (pD 8.5) and under acidic conditions (pD ∼4.0) indicated the conformations of the nucleotides (anti and syn, respectively) and the site of ring protonation (the pyrimidine ring).

Original languageEnglish (US)
Pages (from-to)1564-1569
Number of pages6
JournalJournal of the American Chemical Society
Volume101
Issue number6
StatePublished - 1979
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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