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

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. (C) 2002 Elsevier Science Ltd. All rights reserved

Published in

Carbohydrate Research
2003, volume: 338, number: 1, pages: 85-93
Publisher: ELSEVIER SCI LTD

SLU Authors

• Andersson, Lars

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

• Kenne, Lennart

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

Publication identifier

• DOI: https://doi.org/10.1016/S0008-6215(02)00352-X

Permanent link to this page (URI)

https://res.slu.se/id/publ/521