Determination of the transglycosidation activity of NAD+ glycohydrolases with 4-(2'-alkyl-sulfanyl-vinyl)-pyridine derivatives generating chromophoric NAD+ analogs

Bioorg Chem. 2003 Aug;31(4):288-305. doi: 10.1016/s0045-2068(03)00041-5.

Abstract

The base exchange of nicotinamide with pyridine derivatives 1a-5a, catalyzed by pig brain NAD(+) glycohydrolase and ADP-ribosyl cyclase from Aplysia californica, generated the corresponding NAD(+) analogs 1b-5b. These analogs exhibited a high absorbance band in the visible region. The transglycosidation rate was determined by monitoring the absorbance increase. Among the tested derivatives, (E)-4-[2-(methylsulfanyl)-vinyl]-pyridine 1a was the most suitable substrate for pig brain NAD(+) glycohydrolase while 4-[1,3]-dithiolan-2-ylidenemethyl-pyridine 3a was the most efficient for ADP-ribosyl cyclase from A. californica.

MeSH terms

  • ADP-ribosyl Cyclase / metabolism
  • Animals
  • Aplysia / enzymology
  • Brain / enzymology
  • Catalysis
  • Glycosides / metabolism*
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • NAD / metabolism*
  • NAD+ Nucleosidase / chemistry*
  • NAD+ Nucleosidase / metabolism*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry
  • Pyridines / metabolism*
  • Spectrophotometry
  • Swine

Substances

  • Glycosides
  • Pyridines
  • NAD
  • ADP-ribosyl Cyclase
  • NAD+ Nucleosidase
  • pyridine