Circular dichroism of oligosaccharides containing neuraminic acid

Biochemistry. 1975 Jun 3;14(11):2299-304. doi: 10.1021/bi00682a004.

Abstract

In order to test the usefulness of circular dichroism in stereochemical and structural studies of oligosaccharides of glycoproteins, we measured the circular dichroism (CD) for N-acetylneuraminic acid (NAcNA) and several derivates. By acidic mathanolysis, we have prepared the deacetylated methyl ester, methyl glycoside of NAcNA, as well as a saponified product. Circular dichroism of these compounds allows us to assign the transition due to the amide chromophore. There is a carboxyl n-pi transition at about 220 nm which has a negative CD band associated with it for the beta-methocyneuraminic acid, but changes sign for the methyl ester (methyl (methyl beta-D-neuraminid)ate). We isolated the trisaccharides N-acetylneuraminyl-(2 leads to 3)-beta-D-galactopyranosyl-(1 leads to 4)-D-glucopyranose [(2leads to 3)NAcN-Lac] as well as (2 leads to 6)NAcN-Lac by paper chromatography and compared the CD for each. The two isomers show similar but distinguishable CD patterns, with a weak negative band due to the carboxyl group centered at 225 nm and a stronger positive band at 200 nm containing contributions from both the amide and carboxyl groups.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chromatography, Gas
  • Chromatography, Paper
  • Circular Dichroism / methods*
  • Mass Spectrometry
  • Methylglycosides
  • Neuraminic Acids
  • Oligosaccharides*
  • Sialic Acids*
  • Spectrophotometry, Ultraviolet
  • Spectrum Analysis / methods*

Substances

  • Methylglycosides
  • Neuraminic Acids
  • Oligosaccharides
  • Sialic Acids