Synthesis of oxidized methyl 4-O-methyl-beta-D-glucopyranoside and methyl beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside derivatives as substrates for fluorescence labeling reactions

Carbohydr Res. 2002 Apr 17;337(8):691-700. doi: 10.1016/s0008-6215(02)00048-4.

Abstract

The synthetic cellulose model compounds methyl 4-O-methyl-beta-D-glucopyranoside and methyl 4-O-methyl-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside and related 6-O-protected intermediates were oxidized in good to fair yields using Swern-conditions or bromine/bis(tributyltin) oxide, respectively, to afford compounds containing 6-aldehyde, 3-keto, and 2,3-diketo groups. Cellobiose and oxidized monosaccharides were then labeled with the carbonyl-selective fluorescence marker 9-(7-amino-1,4,7-trioxaheptyl)-9H-carbazolecarboxamide (CCOA). The labeled derivatives serve as model compounds for the determination of minute amounts of carbonyl groups in cellulosic polysaccharides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes
  • Cellobiose
  • Cellulose / chemistry
  • Disaccharides / chemical synthesis
  • Disaccharides / chemistry
  • Fluorescent Dyes / chemistry
  • Ketones
  • Methylglucosides / chemical synthesis*
  • Methylglucosides / chemistry
  • Models, Molecular
  • Oxidation-Reduction
  • Staining and Labeling

Substances

  • Aldehydes
  • Disaccharides
  • Fluorescent Dyes
  • Ketones
  • Methylglucosides
  • Cellobiose
  • methylglucoside
  • Cellulose