title: Isotopic effects in mechanistic studies of biotransformations of fluorine derivatives of L-alanine catalysed by L-alanine dehydrogenase.
abstract: Synthesis of 3-fluoro-[2-2H]-L-alanine (3-F-[2H]-L-Ala) in reductive amination of 3-fluoropyruvic acid catalysed by L-alanine dehydrogenase (AlaDH) was described. Fluorine derivative was used to study oxidative deamination catalysed by AlaDH applied kinetic (for 3-F-L-Ala in H2O - KIE's on Vmax: 1.1; on Vmax/KM: 1.2; for 3-F-L-Ala in2H2O - on Vmax: 1.4; on Vmax/KM: 2.1) and solvent isotope effect methods (for 3-F-L-Ala - SIE's on Vmax: 1.0; on Vmax/KM: 0.87; for 3-F-[2-2H]-L-Ala - on Vmax: 1.4; on Vmax/KM: 1.5). Studies explain some details of reaction mechanism.
authors.affiliation: Department of Biochemistry, 2nd Faculty of Medicine, Medical University of Warsaw, 101 Żwirki i Wigury Ave., 02-089 Warsaw, Poland. Electronic address: jolanta.szymanska@wum.edu.pl.
authors.forename: Jolanta
authors.initials: J
authors.lastname: Szymańska-Majchrzak
authors.affiliation: Department of Chemistry, University of Warsaw, 1 Pasteur Str., 02-093 Warsaw, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Pałka
authors.affiliation: Department of Biochemistry, 2nd Faculty of Medicine, Medical University of Warsaw, 101 Żwirki i Wigury Ave., 02-089 Warsaw, Poland.
authors.forename: Marianna
authors.initials: M
authors.lastname: Kańska
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D050788:Alanine Dehydrogenase / Q000378:metabolism*; D055162:Biocatalysis; D001711:Biotransformation; D003641:Deamination; D003903:Deuterium / Q000737:chemistry; D007700:Kinetics; D008956:Models, Chemical; D010084:Oxidation-Reduction; D012997:Solvents
chemical_list: D012997:Solvents; C007742:3-fluoroalanine; D003903:Deuterium; D050788:Alanine Dehydrogenase; D000409:Alanine
keywords: Deuterium; Fluorine; Isotope effect; L-alanine; L-alanine dehydrogenase; UV–VIS spectrophotometry