In-vitro biotransformation of 3-nitropropanol (miserotoxin aglycone) by horse liver alcohol dehydrogenase.
The oxidation of 3-nitropropanol (NPOH) by equine alcohol dehydrogenase (ADH) was examined by HPLC. The intermediate product, 3-nitropropanal (NPAL), was synthesized and it was also trapped in the reaction mixture as the semicarbazone. At neutral pH, NPAL spontaneously decomposed to nitrite and acrolein but in the presence of ADH, NPAL was partially oxidized to 3-nitropropionic acid (NPA). HPLC conditions are described which simultaneously resolve the components of the reaction mixtures. However, the results from previous studies suggest an efficient conversion of NPOH to NPA in vivo without the spontaneous formation of acrolein.
Benn
M H
MH
Department of Chemistry, University of Calgary, Alberta, Canada.
McDiarmid
R E
RE
Majak
W
W
D000433:1-Propanol / Q000493:pharmacokinetics; D000426:Alcohol Dehydrogenase / Q000378:metabolism*; D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D006736:Horses / Q000378:metabolism*; D066298:In Vitro Techniques; D008099:Liver / Q000201:enzymology*; D009574:Nitro Compounds / Q000032:analysis; D010084:Oxidation-Reduction; D020005:Propanols
D009574:Nitro Compounds; D020005:Propanols; C024522:3-nitro-1-propanol; D000433:1-Propanol; D000426:Alcohol Dehydrogenase