Boronate based metal-free platform for diphosphate-specific molecular recognitions

Org Lett. 2015 Feb 6;17(3):588-91. doi: 10.1021/ol5036003. Epub 2015 Jan 16.

Abstract

A reversible boronate-diol interaction provides a versatile synthetic platform for molecular recognitions whose binding specificity can be molecularly tailored. We found that boronate derivatives with relatively strong acidity generally undergo a diphosphate-specific recognition among other phosphates under weakly acidic pH conditions, a feature relevant to DNA sequencing. (11)B and (31)P NMR studies identified "tetrahedral boronate and divalent diphosphate" as a pair responsible for forming a 1:1 stoichiometric complex, which manifests as a unique pH-dependent stability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Boronic Acids / chemistry*
  • DNA / chemistry
  • Diphosphates / chemical synthesis*
  • Diphosphates / chemistry
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Alcohols
  • Boronic Acids
  • Diphosphates
  • DNA