Determination of the transglycosidation activity of NAD+ glycohydrolases with 4-(2'-alkyl-sulfanyl-vinyl)-pyridine derivatives generating chromophoric NAD+ analogs.
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.
Pacaud
Karine
K
Laboratoire de Chimie Organique Biologique, UMR7123, Faculté de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, FR-67008, Cedex, Strasbourg, France.
Tritsch
Denis
D
Burger
Alain
A
Biellmann
Jean François
JF
D036541:ADP-ribosyl Cyclase / Q000378:metabolism; D000818:Animals; D001048:Aplysia / Q000201:enzymology; D001921:Brain / Q000201:enzymology; D002384:Catalysis; D006027:Glycosides / Q000378:metabolism*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009243:NAD / Q000378:metabolism*; D009244:NAD+ Nucleosidase / Q000737:chemistry* / Q000378:metabolism*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D013053:Spectrophotometry; D013552:Swine
D006027:Glycosides; D011725:Pyridines; D009243:NAD; D036541:ADP-ribosyl Cyclase; D009244:NAD+ Nucleosidase; C023666:pyridine