The absolute configuration of 1-carboxyethyl substituents on common hexoses by circular dichroism

Carbohydr Res. 2003 Jan 2;338(1):85-93. doi: 10.1016/s0008-6215(02)00352-x.

Abstract

Determination of the absolute configuration of the 1-carboxyethyl substituent on a monosaccharide by circular dichroism measurements was found to be a sensitive and simple method. It relies on comparison of the spectrum of a 1-carboxyethyl substituted sugar or sugar derivative with the spectra of (R)- and (S)-lactic acid in the region 200-260 nm in which the (R)- and (S)-configuration give negative and positive deltaepsilon, respectively. The oligo- or poly-saccharide containing a 1-carboxyethyl substituted sugar is hydrolyzed to monomers and the 1-carboxyethyl substituted sugar isolated by chromatography. The CD spectrum obtained for the 1-carboxyethyl substituted sugar in water solution at pH 2 is then compared with spectra of (R)- and (S)-lactic acid. The sign for the absorption and a maximum of comparable intensity and appearance around 210 nm, identify the stereochemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism*
  • Hexoses / chemistry*
  • Ketones
  • Molecular Structure
  • Stereoisomerism

Substances

  • Hexoses
  • Ketones