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

Maria L. Pellizzaro; Simon A. Barrett; Julie Fisher; Andrew J. Wilson

doi:10.1039/c2ob25333j

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

Maria L. Pellizzaro, Simon A. Barrett, Julie Fisher, Andrew J. Wilson^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

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. 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.

Original language	English
Pages (from-to)	4899-4906
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	25
DOIs	https://doi.org/10.1039/c2ob25333j
Publication status	Published - 7 Jul 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Fisher, Julie

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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