Tuning the specificity of a synthetic receptor using a selected nucleic acid receptor

J Am Chem Soc. 2004 Dec 22;126(50):16515-9. doi: 10.1021/ja0478476.

Abstract

Because of their relative simplicity, synthetic receptors often lack the selectivity observed for biopolymer receptors, such as aptamers. However, aptamer recognition of ligands is limited by the chemistries inherent in the four canonical nucleotides. Here, we report the design and selection of a ternary complex in which the specificity of a bis-boronic acid synthetic host (1) that binds to various carboxylic acids is tuned by a surrounding aptamer. Although, the synthetic receptor alone has higher selectivity for citrate over DL-tartrate, the formation of the aptamer:receptor complex reversed the organic host selectivity to preferentially bind tartrate. The RNA conformation changed upon the introduction of the synthetic host, consistent with an induced-fit mechanism for binding.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Base Sequence
  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Glyoxal / analogs & derivatives
  • Molecular Sequence Data
  • Nucleic Acid Conformation
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • RNA / chemistry*
  • Receptors, Cell Surface / chemistry*
  • Sepharose / analogs & derivatives
  • Substrate Specificity
  • Tartrates / chemistry

Substances

  • Boronic Acids
  • Oligonucleotides
  • Receptors, Cell Surface
  • Tartrates
  • Glyoxal
  • RNA
  • Sepharose
  • tartaric acid