Synthesis and evaluation of mimetics of UDP and UDP-alpha-D-galactose, dTDP and dTDP-alpha-D-glucose with monosaccharides replacing the key pyrophosphate unit

Org Biomol Chem. 2005 Mar 21;3(6):1109-15. doi: 10.1039/b500418g. Epub 2005 Feb 21.

Abstract

A series of 5'-O-glycosyl-uridine and thymidine derivatives have been prepared as potential mimics of sugar nucleotides and nucleotide-diphosphates. These compounds proved not to be inhibitors of bovine beta-1,4-galactosyltransferase although some showed moderate inhibition of Salmonella dTDP-alpha-D-glucose 4,6-dehydratase (RmlB).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biomimetics*
  • Cattle
  • Diphosphates / chemistry*
  • Diphosphates / metabolism
  • Glucose / analogs & derivatives*
  • Glucose / chemistry
  • Glucose / metabolism
  • Hydro-Lyases / drug effects
  • Hydro-Lyases / metabolism
  • Monosaccharides / chemistry*
  • Monosaccharides / metabolism
  • N-Acetyllactosamine Synthase / drug effects
  • N-Acetyllactosamine Synthase / metabolism
  • Salmonella enterica / enzymology
  • Thymine Nucleotides / chemistry*
  • Thymine Nucleotides / metabolism
  • Uridine Diphosphate / chemistry*
  • Uridine Diphosphate / metabolism
  • Uridine Diphosphate Galactose / chemistry*
  • Uridine Diphosphate Galactose / metabolism

Substances

  • Diphosphates
  • Monosaccharides
  • Thymine Nucleotides
  • deoxythymidine diphosphate-glucose
  • Uridine Diphosphate Galactose
  • Uridine Diphosphate
  • N-Acetyllactosamine Synthase
  • Hydro-Lyases
  • dTDPglucose 4,6-dehydratase
  • Glucose