title: N-acylethanolamines as novel alcohol dehydrogenase 3 substrates.
abstract: N-acylethanolamines (NAEs) are members of the fatty acid amide family. The NAEs have been proposed to serve as metabolic precursors to N-acylglycines (NAGs). The sequential oxidation of the NAEs by an alcohol dehydrogenase and an aldehyde dehydrogenase would yield the N-acylglycinals and/or the NAGs. Alcohol dehydrogenase 3 (ADH3) is one enzyme that might catalyze this reaction. To define a potential role for ADH3 in NAE catabolism, we synthesized a set of NAEs and evaluated these as ADH3 substrates. NAEs were oxidized by ADH3, yielding the N-acylglycinals as the product. The (V/K)(app) values for the NAEs included here were low relative to cinnamyl alcohol. Our data show that the NAEs can serve as alcohol dehydrogenase substrates.
authors.affiliation: Department of Chemistry, University of South Florida, 4202 E. Fowler Ave., CHE 205, Tampa, FL 33620-5250, USA.
authors.forename: Milena
authors.initials: M
authors.lastname: Ivkovic
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Dempsey
authors.forename: Sumit
authors.initials: S
authors.lastname: Handa
authors.forename: Joshua H
authors.initials: JH
authors.lastname: Hilton
authors.forename: Edward W
authors.initials: EW
authors.lastname: Lowe
authors.forename: David J
authors.initials: DJ
authors.lastname: Merkler
mesh_terms: D000426:Alcohol Dehydrogenase / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D004983:Ethanolamines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D066298:In Vitro Techniques; D007700:Kinetics; D008099:Liver / Q000201:enzymology; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D013379:Substrate Specificity
chemical_list: D004983:Ethanolamines; C022203:N-acylethanolamines; D000426:Alcohol Dehydrogenase