Synthesis of pyridine nucleotide analogs consisting of nicotinoylamino acids by means of transglycosidation reactions catalyzed by mammalian pyridine nucleotide transglycosidases.
Besides isonicotinic acid analogs of pyridine nucleotides, 24 novel pyridine nucleotide cofactors that have an amino acid residue at the carbonyl carbon of the nicotinamide moiety have been prepared by means of transglycosidation reactions catalyzed by rabbit spleen and guinea pig spleen pyridine nucleotide transglycosidases. Their chemical properties were characterized by means of proton NMR, Fab-mass, and UV spectral measurement and phosphodiesterase digestion. Except for the isonicotinic acid ones, these nicotinoylamino acid analogs were shown to function as substrates for both the hydrolysis and the transglycosidation reactions catalyzed by the mammalian NAD glycohydrolases, though their substrate activities were lower than those with the original pyridine nucleotides (NMN, NAD, and NADP). They were inactive in regard to yeast alcohol dehydrogenase- and Thermoanaerobium brockii alcohol dehydrogenase (NADP dependent)-oxidation.
D000818:Animals; D002384:Catalysis; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006168:Guinea Pigs; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009097:Multienzyme Complexes / Q000378:metabolism*; D009699:N-Glycosyl Hydrolases / Q000378:metabolism*; D009243:NAD / Q000031:analogs & derivatives* / Q000378:metabolism; D009249:NADP / Q000031:analogs & derivatives* / Q000378:metabolism; D009537:Nicotinamide Mononucleotide / Q000031:analogs & derivatives* / Q000378:metabolism; D011817:Rabbits; D013154:Spleen / Q000737:chemistry / Q000201:enzymology*; D014166:Transferases / Q000378:metabolism*
D009097:Multienzyme Complexes; C023176:transglycosidase enzyme system; D009243:NAD; D009537:Nicotinamide Mononucleotide; D009249:NADP; D014166:Transferases; D006026:Glycoside Hydrolases; D009699:N-Glycosyl Hydrolases; C062627:pyridine nucleotide glycohydrolase (rabbit spleen)