Synthesis of 7-O-(2-deoxy-2-sulfamido-alpha-D-glucopyranosyl)-4-methylcoumarin sodium salt: a fluorogenic substrate for sulfamidase

Carbohydr Res. 2002 Jun 5;337(11):1055-8. doi: 10.1016/s0008-6215(02)00088-5.

Abstract

The title compound, useful for testing the efficacy of heparin sulfamidase, was synthesized in good yield starting from 2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl fluoride, reducing the azido group efficiently with SnCl(2)-PhSH-Et(3)N reagent and finally crystallizing the N-sulfated product from methanol after deacetylation.

MeSH terms

  • Coumarins / chemical synthesis*
  • Fluorescent Dyes
  • Hydrolases / metabolism*
  • Monosaccharides / chemical synthesis*
  • Mucopolysaccharidosis III / metabolism
  • Substrate Specificity

Substances

  • 7-O-(2-deoxy-2-sulfamido-alpha-D-glucopyranosyl)-4-methylcoumarin sodium salt
  • Coumarins
  • Fluorescent Dyes
  • Monosaccharides
  • Hydrolases
  • N-sulfoglucosamine sulfohydrolase