Jump to main content
Jump to site search

Issue 25, 2012
Previous Article Next Article

Design, synthesis and binding studies of a novel quadruple ADDA hydrogen-bond array

Author affiliations

Abstract

The design and synthesis of a novel ADDA hydrogen-bond array is described. The ureidodiimidazole motif (UDIM) 2 engages in interactions with complementary diamidonaphthyridine (DAN) 3 motifs with an association constant Ka = 825 ± 16 M−1 in chloroform. 1H NMR and molecular modelling studies were carried out in order to explain the unexpected behaviour of this new supramolecular motif. These revealed that a combination of effects including; an energetic bias for the folded conformer, subtle differences in shape complementarity between the two components and the potential for self-association of UDIM 2 disfavour higher affinity interactions between the two components.

Graphical abstract: Design, synthesis and binding studies of a novel quadruple ADDA hydrogen-bond array

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 12 Oct 2011, accepted on 30 Apr 2012 and first published on 01 May 2012


Article type: Paper
DOI: 10.1039/C2OB25333J
Citation: Org. Biomol. Chem., 2012,10, 4899-4906
  •   Request permissions

    Design, synthesis and binding studies of a novel quadruple ADDA hydrogen-bond array

    M. L. Pellizzaro, S. A. Barrett, J. Fisher and A. J. Wilson, Org. Biomol. Chem., 2012, 10, 4899
    DOI: 10.1039/C2OB25333J

Search articles by author