An enantioselective fluorescent sensor for sugar acids

J Am Chem Soc. 2004 Dec 15;126(49):16179-86. doi: 10.1021/ja046289s.

Abstract

Chiral fluorescent boronic acid 1 was found to be a highly enantioselective, chemoselective, and sensitive sensor for sugar acids, such as tartaric acid. Enantioselectivities (K(R)/K(S)) of up to 550:1, chemoselectivity up to 11,000:1, and sensitivities in the micromolar range with sensor 1 were observed. Single-crystal X-ray analysis was used to confirm the structure of the fluorescent species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / analysis
  • Boronic Acids / chemistry
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism
  • Hydrogen-Ion Concentration
  • Kinetics
  • Models, Molecular
  • Spectrometry, Fluorescence
  • Stereoisomerism
  • Sugar Acids / analysis*
  • Sugar Acids / chemistry
  • Sugar Acids / metabolism
  • Titrimetry

Substances

  • Boronic Acids
  • Fluorescent Dyes
  • Sugar Acids