title: Comparative oxidation of 2-propyn-1-ol with other low molecular weight unsaturated and saturated primary alcohols by bovine liver catalase in vitro.
abstract: The oxidative metabolism of low molecular weight, saturated and unsaturated, primary alcohols, which include ethanol, allyl alcohol (2-propen-1-ol), and propargyl alcohol (2-propyn-1-ol), is generally accepted to occur via alcohol dehydrogenase; however, compared to other short-chain alcohols, 2-propyn-1-ol is a poor substrate for this enzyme. Accordingly, we have examined liver catalase as an alternative pathway for the oxidation or bioactivation of 2-propyn-1-ol to 2-propyn-1-al, a highly reactive alpha,beta-unsaturated aldehyde. The rates of oxidation for a series of low molecular weight, saturated, primary alcohols and selected unsaturated alcohols were determined for the bovine liver catalase-catalyzed reaction by measuring aldehyde production over time employing a GC procedure. A negative correlation was found for log rates of oxidation versus molecular size (volume) of the substrates (p < 0.01); however, the rate of oxidation for 2-propyn-1-ol was higher than predicted by this relation and was 30% greater than the oxidation rate determined for ethanol. In addition, 2-propyn-1-ol-derived 2-propyn-1-al inhibited the peroxidatic and catalytic activities of catalase, whereas 2-propen-1-ol-derived 2-propen-1-al had no effect on these activities of catalase. Inhibition was blocked by GSH; and the activity was not restored to the inhibited enzyme by GSH treatment or dialysis.(ABSTRACT TRUNCATED AT 250 WORDS)
authors.affiliation: Medical Research Laboratories, Veterans Affairs Medical Center, Minneapolis, Minnesota 55417.
authors.forename: E G
authors.initials: EG
authors.lastname: DeMaster
authors.forename: T
authors.initials: T
authors.lastname: Dahlseid
authors.forename: B
authors.initials: B
authors.lastname: Redfern
mesh_terms: D000433:1-Propanol / Q000737:chemistry / Q000378:metabolism; D000447:Aldehydes / Q000378:metabolism; D000480:Alkynes / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D002374:Catalase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D002417:Cattle; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism*; D005949:Glucose Oxidase / Q000378:metabolism; D005978:Glutathione / Q000494:pharmacology; D008099:Liver / Q000201:enzymology*; D008970:Molecular Weight; D010084:Oxidation-Reduction; D020005:Propanols
chemical_list: D000447:Aldehydes; D000480:Alkynes; D005233:Fatty Alcohols; D020005:Propanols; D000433:1-Propanol; C028255:propargyl alcohol; D005949:Glucose Oxidase; D002374:Catalase; D005978:Glutathione