Discovery of linear receptors for multiple dihydrogen phosphate ions using dynamic combinatorial chemistry

Sophie R. Beeren, Jeremy K M Sanders

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

We describe the use of dynamic combinatorial chemistry to discover a new series of linear hydrazone-based receptors that bind multiple dihydrogen phosphate ions. Through the use of a template-driven, selection-based approach to receptor synthesis, dynamic combinatorial chemistry allows for the identification of unexpected host structures and binding motifs. Notably, we observed the unprecedented selection of these linear receptors in preference to competing macrocyclic hosts. Furthermore, linear receptors containing up to nine building blocks and three different building blocks were amplified in the dynamic combinatorial library. The receptors were formed using a dihydrazide building block based on an amino acid-disubstituted ferrocene scaffold. A detailed study of the linear pentamer revealed that it forms a helical ditopic receptor that employs four acylhydrazone hydrogen-bond donor motifs to cooperatively bind two dihydrogen phosphate ions.
Original languageEnglish
JournalJournal of the American Chemical Society
Volume133
Issue number11
Pages (from-to)3804-3807
Number of pages4
ISSN0002-7863
DOIs
Publication statusPublished - 2011
Externally publishedYes

Keywords

  • Chemistry (all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry
  • Binding motif
  • Building blockes
  • Dihydrogen phosphate
  • Ditopic receptors
  • Dynamic combinatorial chemistry
  • Dynamic combinatorial library
  • Ferrocenes
  • Host structure
  • Hydrazones
  • Hydrogen-bond donors
  • Macrocyclics
  • New series
  • Pentamers
  • Amino acids
  • Bioassay
  • Biochips
  • Iron compounds
  • Scaffolds
  • Ions
  • Dihydrazide
  • Dihydrogen phosphate ion
  • Ferrocene
  • Hydrazide derivative
  • hydrazone derivative
  • Molecular scaffold
  • Receptor
  • Unclassified drug
  • Amino acid substitution
  • Article
  • Combinatorial chemistry
  • Hydrogen bond
  • Rceptor binding
  • Synthesis
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Combinatorial Chemistry Techniques
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Phosphoric Acids

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