Synthesis of glucose derivatives modified at the 4-OH as potential chain-terminators of cellulose biosynthesis; herbicidal activity of simple monosaccharide derivatives

Org Biomol Chem. 2009 Mar 21;7(6):1097-105. doi: 10.1039/b820830a. Epub 2009 Jan 30.

Abstract

A series of D-glucose derivatives that have been modified at C-4 were synthesised from D-galactose as potential chain terminators of cellulose biosynthesis. Two compounds displayed herbicidal activity in pre-emergence tests and in addition a cell expansion assay at higher concentrations revealed symptomology of a third compound that was indicative of inhibition of cellulose biosynthesis.

MeSH terms

  • Cellulose / antagonists & inhibitors*
  • Cellulose / biosynthesis*
  • Cellulose / chemistry
  • Dose-Response Relationship, Drug
  • Galactose / chemistry
  • Glucose / analogs & derivatives
  • Glucose / chemical synthesis*
  • Glucose / pharmacology*
  • Molecular Structure
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry
  • Monosaccharides / pharmacology*
  • Nicotiana / cytology
  • Nicotiana / drug effects
  • Nicotiana / metabolism
  • Stereoisomerism

Substances

  • Monosaccharides
  • Cellulose
  • Glucose
  • Galactose