Differences in heterocycle basicity distinguish homocysteine from cysteine using aldehyde-bearing fluorophores

Chem Commun (Camb). 2014 Aug 4;50(60):8219-22. doi: 10.1039/c4cc03527e.

Abstract

We report the detection of homocysteine over cysteine based upon characteristic differences between 5- and 6-membered heterocyclic amines formed upon reaction with aldehyde-bearing compounds. Homocysteine-derived thiazinane-4-carboxylic acids are more basic than cysteine-derived thiazolidines-4-carboxylic acids. Fluorescence enhancement in response to homocysteine is achieved by tuning pH and excitation wavelength.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemistry*
  • Alkalies / chemistry*
  • Cysteine / analysis*
  • Fluorescent Dyes / chemistry*
  • Homocysteine / analysis*
  • Hydrogen-Ion Concentration
  • Models, Molecular
  • Molecular Structure
  • Spectrometry, Fluorescence
  • Thiazolidines

Substances

  • Aldehydes
  • Alkalies
  • Fluorescent Dyes
  • Thiazolidines
  • Homocysteine
  • thiazolidine-4-carboxylic acid
  • Cysteine