Reaction of ozone with nicotinamide and its derivatives

doi:10.1016/0003-9861(74)90322-1

Archives of Biochemistry and Biophysics

Volume 161, Issue 2, April 1974, Pages 408-419

https://doi.org/10.1016/0003-9861(74)90322-1 Get rights and content

Abstract

Reaction of ozone with NADH eliminated the 340 nm absorbance. The 260 nm absorbance increased initially and then slowly declined. Equimolar amounts of NADH and ozone reacted. Products were separated by ion exchange chromatography and were shown to contain only traces of NAD. The products were not active in the alcohol dehydrogenase assay and did not form cyanide complexes. There was no reaction of NAD with ozone. NADPH and NADP showed the same reactivities as NADH and NAD. The reactions were not influenced by pH in the range 4.6–9.0. When NADH and tryptophan, or NADH and methionine, or NADH and glutathione (at low concentration) were competitors for available ozone, NADH was preferentially oxidized. Treatment of aqueous solutions of 1,4-dihydro-1-methyl nicotinamide with ozone caused changes in the absorbance spectrum consistent with ozonolysis of the 5,6 double bond. The product has been isolated after ozonolysis in methylene chloride and characterized by uv, ir, mass spectroscopy, and elemental analysis. Results were consistent with the reaction:

Further ozonolysis cleaved the 2,3 double bond. Reaction of NADH with ozone resulted in analogous reactions. The adenine moiety was resistant to ozonolysis, but this reaction was pH dependent, being greater at neutral and alkaline pH.

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Reaction of ozone with nicotinamide and its derivatives

Abstract

Atmos. Environ

Atmos. Environ

Arch. Environ. Health

Arch. Biochem. Biophys

J. Liebigs Ann. Chem

J. Chromatogr

J. Chromatogr

Chem. Phys. Lipids

Ind. Eng. Chem

Photochemistry of Air Pollution

J. Reticuloendothel. Soc

Science