Synthesis and anion-binding properties of new disulfonamide-based receptors

Oscar Mammoliti; Sara Allasia; Sally Dixon; Jeremy Dunbar Kilburn

doi:10.1016/j.tet.2009.01.070

Synthesis and anion-binding properties of new disulfonamide-based receptors

Oscar Mammoliti, Sara Allasia, Sally Dixon, Jeremy Dunbar Kilburn

University of Southampton

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

14 Citations (Scopus)

Abstract

The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d(3) with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. L-Valine derived macrocycles maintain tight 1:1 binding of acetate (K-a(1:1) >10(4) M-1) in MeCN-d(3) and display preference for oxyanion binding in more competitive MeCN-d(3)/2% H2O. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2184-2195
Number of pages	12
Journal	Tetrahedron
Volume	65
Issue number	11
Early online date	21 Jan 2009
DOIs	https://doi.org/10.1016/j.tet.2009.01.070
Publication status	Published - 14 Mar 2009

Keywords

AMINO-ACID RECOGNITION
N-PROTECTED GLUTAMATE
MOLECULAR RECOGNITION
PEPTIDE RECEPTORS
SOLID-STATE
CARBOXYLATE BINDING
GUANIDINIOCARBONYL PYRROLES
ACYCLIC RECEPTORS
COMPLEX STABILITY
SELECTIVE BINDING

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title = "Synthesis and anion-binding properties of new disulfonamide-based receptors",

abstract = "The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d(3) with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. L-Valine derived macrocycles maintain tight 1:1 binding of acetate (K-a(1:1) >10(4) M-1) in MeCN-d(3) and display preference for oxyanion binding in more competitive MeCN-d(3)/2% H2O. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "AMINO-ACID RECOGNITION, N-PROTECTED GLUTAMATE, MOLECULAR RECOGNITION, PEPTIDE RECEPTORS, SOLID-STATE, CARBOXYLATE BINDING, GUANIDINIOCARBONYL PYRROLES, ACYCLIC RECEPTORS, COMPLEX STABILITY, SELECTIVE BINDING",

author = "Oscar Mammoliti and Sara Allasia and Sally Dixon and Kilburn, {Jeremy Dunbar}",

year = "2009",

month = mar,

day = "14",

doi = "10.1016/j.tet.2009.01.070",

language = "English",

volume = "65",

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journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis and anion-binding properties of new disulfonamide-based receptors

AU - Mammoliti, Oscar

AU - Allasia, Sara

AU - Dixon, Sally

AU - Kilburn, Jeremy Dunbar

PY - 2009/3/14

Y1 - 2009/3/14

N2 - The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d(3) with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. L-Valine derived macrocycles maintain tight 1:1 binding of acetate (K-a(1:1) >10(4) M-1) in MeCN-d(3) and display preference for oxyanion binding in more competitive MeCN-d(3)/2% H2O. (C) 2009 Elsevier Ltd. All rights reserved.

AB - The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d(3) with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. L-Valine derived macrocycles maintain tight 1:1 binding of acetate (K-a(1:1) >10(4) M-1) in MeCN-d(3) and display preference for oxyanion binding in more competitive MeCN-d(3)/2% H2O. (C) 2009 Elsevier Ltd. All rights reserved.

KW - AMINO-ACID RECOGNITION

KW - N-PROTECTED GLUTAMATE

KW - MOLECULAR RECOGNITION

KW - PEPTIDE RECEPTORS

KW - SOLID-STATE

KW - CARBOXYLATE BINDING

KW - GUANIDINIOCARBONYL PYRROLES

KW - ACYCLIC RECEPTORS

KW - COMPLEX STABILITY

KW - SELECTIVE BINDING

U2 - 10.1016/j.tet.2009.01.070

DO - 10.1016/j.tet.2009.01.070

M3 - Article

SN - 0040-4020

VL - 65

SP - 2184

EP - 2195

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Synthesis and anion-binding properties of new disulfonamide-based receptors

Abstract

Keywords

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