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

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

    Research output: Contribution to journalArticle

    13 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 languageEnglish
    Pages (from-to)2184-2195
    Number of pages12
    JournalTetrahedron
    Volume65
    Issue number11
    Early online date21 Jan 2009
    DOIs
    Publication statusPublished - 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

    Cite this

    Mammoliti, O., Allasia, S., Dixon, S., & Kilburn, J. D. (2009). Synthesis and anion-binding properties of new disulfonamide-based receptors. Tetrahedron, 65(11), 2184-2195. https://doi.org/10.1016/j.tet.2009.01.070

    Synthesis and anion-binding properties of new disulfonamide-based receptors. / Mammoliti, Oscar; Allasia, Sara; Dixon, Sally; Kilburn, Jeremy Dunbar.

    In: Tetrahedron, Vol. 65, No. 11, 14.03.2009, p. 2184-2195.

    Research output: Contribution to journalArticle

    Mammoliti, O, Allasia, S, Dixon, S & Kilburn, JD 2009, 'Synthesis and anion-binding properties of new disulfonamide-based receptors', Tetrahedron, vol. 65, no. 11, pp. 2184-2195. https://doi.org/10.1016/j.tet.2009.01.070
    Mammoliti, Oscar ; Allasia, Sara ; Dixon, Sally ; Kilburn, Jeremy Dunbar. / Synthesis and anion-binding properties of new disulfonamide-based receptors. In: Tetrahedron. 2009 ; Vol. 65, No. 11. pp. 2184-2195.
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    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.",
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    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.

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    KW - CARBOXYLATE BINDING

    KW - GUANIDINIOCARBONYL PYRROLES

    KW - ACYCLIC RECEPTORS

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    KW - SELECTIVE BINDING

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