Synthesis of an allergy inducing tetrasaccharide "4P-X"

Carbohydr Res. 2017 Feb 1:439:44-49. doi: 10.1016/j.carres.2016.11.013. Epub 2016 Nov 27.

Abstract

4P-X (β-D-galactopyranosyl-(1 → 4)-β-D-galactopyranosyl-(1 → 6)-[β-D-galactopyranosyl-(1 → 4)]-β-D-glucopyranose) is included in galacto-oligosaccharides (GOSs) produced by β-galactosidase derived from Bacillus circulans. 4P-X has been known to induce particularly strong allergies. High purity 4P-X is essential for use as a standard to quantify the amount of 4P-X in GOSs; however, the isolation of high purity 4P-X has never been reported. In this study, we achieved the synthesis of 4P-X by a combination of organic and enzymatic chemical syntheses in a short time. This is the first report of isolated, high purity 4P-X.

Keywords: 4P-X; Allergy; Galacto-oligosaccharides; Oligosaccharide synthesis.

MeSH terms

  • Bacillus / chemistry
  • Bacillus / enzymology
  • Bacterial Proteins / chemistry*
  • Disaccharides / chemistry
  • Galactose / chemistry*
  • Humans
  • Hypersensitivity / etiology
  • Hypersensitivity / immunology
  • Lactose / chemistry
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / isolation & purification*
  • Oligosaccharides / pharmacology
  • beta-Galactosidase / chemistry*

Substances

  • Bacterial Proteins
  • Disaccharides
  • Oligosaccharides
  • 6-O-galactopyranosylgalactose
  • beta-Galactosidase
  • Lactose
  • Galactose