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

Access to Document

10.1039/c2ob25333j

Cite this

@article{62289bc6170045499ef94e13985a5658,

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 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.",

author = "Pellizzaro, \{Maria L.\} and Barrett, \{Simon A.\} and Julie Fisher and Wilson, \{Andrew J.\}",

year = "2012",

month = jul,

day = "7",

doi = "10.1039/c2ob25333j",

language = "English",

volume = "10",

pages = "4899--4906",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "25",

}

TY - JOUR

T1 - Design, synthesis and binding studies of a novel quadruple ADDA hydrogen-bond array

AU - Pellizzaro, Maria L.

AU - Barrett, Simon A.

AU - Fisher, Julie

AU - Wilson, Andrew J.

PY - 2012/7/7

Y1 - 2012/7/7

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/84862189522

U2 - 10.1039/c2ob25333j

DO - 10.1039/c2ob25333j

M3 - Article

AN - SCOPUS:84862189522

SN - 1477-0520

VL - 10

SP - 4899

EP - 4906

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 25

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this