Synthesis and biological evaluation of 5'-glycyl derivatives of uridine as inhibitors of 1,4-β-galactosyltransferase

Bioorg Chem. 2015 Feb:58:18-25. doi: 10.1016/j.bioorg.2014.11.001. Epub 2014 Nov 10.

Abstract

New 5'-glycyl derivatives of uridine containing fragments of varying lipophilicity were synthesized as analogues of natural peptidyl antibiotics. One of the studied compounds, 5'-O-(N-succinylglycyl)-2',3'-O-isopropylideneuridine (A4), showed moderate inhibition against 1,4-β-galactosyltransferase. However, additional studies showed that the observed inhibitory effect was due to binding to bovine serum albumin, which was used in assays as a stabilizer.

Keywords: Glycosyltransferase inhibitors; Peptidyl nucleoside; Uridine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Galactosyltransferases / antagonists & inhibitors*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis
  • Uridine / pharmacology

Substances

  • Enzyme Inhibitors
  • Galactosyltransferases
  • Uridine