Development of a (1)H NMR structural-reporter-group concept for the analysis of prebiotic galacto-oligosaccharides of the [β-d-Galp-(1→x)]n-d-Glcp type

Carbohydr Res. 2014 Dec 5:400:54-58. doi: 10.1016/j.carres.2014.08.011. Epub 2014 Sep 1.

Abstract

Some β-galactosidases (EC 3.2.1.23) are capable of producing mixtures of linear and branched galacto-oligosaccharides (GOS) with various types of glycosidic linkages [degree of polymerization (DP) 2-8; mainly GalnGlc] when incubated under specific conditions with lactose. These products are generally applied in infant formula. However, for most galacto-oligosaccharide products only major components (low DP) or linkage patterns have been described. To build up a library of (1)H and (13)C NMR data, a detailed NMR study on commercially available GOS di- and trisaccharides, and some larger GOS oligosaccharides was carried out. Based on the fully assigned (1)H and (13)C chemical shifts of these model compounds, a (1)H NMR structural-reporter-group concept was formulated to function as a tool in the structural analysis of single GOS components and GOS mixtures.

Keywords: Galacto-oligosaccharides; NMR spectroscopy; Prebiotics; Structural-reporter-group concept.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Radioisotopes / chemistry
  • Galactose / chemistry*
  • Hydrogen / chemistry
  • Magnetic Resonance Spectroscopy*
  • Oligosaccharides / chemistry*
  • Prebiotics
  • beta-Galactosidase / chemistry*
  • beta-Galactosidase / metabolism

Substances

  • Carbon Radioisotopes
  • Oligosaccharides
  • Prebiotics
  • Hydrogen
  • beta-Galactosidase
  • Galactose