title: Design, synthesis and binding studies of a novel quadruple ADDA hydrogen-bond array.
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 K(a) = 825 ± 16 M(-1) in chloroform. (1)H 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.
authors.affiliation: School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK.
authors.forename: Maria L
authors.initials: ML
authors.lastname: Pellizzaro
authors.forename: Simon A
authors.initials: SA
authors.lastname: Barrett
authors.forename: Julie
authors.initials: J
authors.lastname: Fisher
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Wilson
mesh_terms: D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena