NDLI: Enzymatic kinetic parameters for polyfluorinated alkyl phosphate hydrolysis by alkaline phosphatase.

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Enzymatic kinetic parameters for polyfluorinated alkyl phosphate hydrolysis by alkaline phosphatase.

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Enzymatic kinetic parameters for polyfluorinated alkyl phosphate hydrolysis by alkaline phosphatase.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Jackson, Derek A. Mabury, Scott A.
Description	Country affiliation: Canada Author Affiliation: Jackson DA ( Department of Chemistry, University of Toronto, Toronto, Ontario, Canada.)
Abstract	The hydrolysis kinetics of three polyfluorinated alkyl phosphate monoesters (monoPAPs), differing in fluorinated chain length, were measured using bovine intestinal alkaline phosphatase to catalyze the reaction. Kinetic values were also measured for analogous hydrogenated phosphate monoesters to elucidate the effects of the fluorinated chain on the rate of enzymatic hydrolysis. Michaelis constants (K(m)) were obtained by a competition kinetics technique in the presence of p-nitrophenyl phosphate (PNPP) using UV-vis spectroscopy. Compared with K(m) (PNPP), Michaelis constants for monoPAPs ranged from 0.9 to 2.1 compared with hydrogenated phosphates, which ranged from 4.0 to 13.0. Apparent bimolecular rate constants (k(cat)/K(m)) were determined by monitoring rates of product alcohol formation at low substrate concentrations using gas chromatography-mass spectrometry. The experimental values for k(cat)/K(m) averaged as 1.1 × 10(7) M(-1) s(-1) for monoPAPs compared with 3.8 × 10(5) M(-1) s(-1) for hexyl phosphate. This suggests that the electron-withdrawing nature of the fluorinated chain enhanced the alcohol leaving group ability. The results were used in a simple model to suggest that monoPAPs in a typical mammalian digestive tract would hydrolyze in approximately 100 s, supporting a previous study that showed its absence after a dosing study in rats.
File Format	HTM / HTML
ISSN	07307268
Issue Number	9
Volume Number	31
e-ISSN	15528618
Journal	Environmental Toxicology and Chemistry
Language	English
Publisher	Wiley
Publisher Date	2012-09-01
Publisher Place	United States
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Research Support, Non-u.s. Gov't Gastrointestinal Tract Discipline Environmental Health Organophosphorus Compounds Rats Discipline Toxicology Alkaline Phosphatase Hydrocarbons, Fluorinated Metabolism Journal Article Organophosphates Hydrolysis Chemistry Animals Cattle Models, Biological Discipline Chemistry Nitrophenols Catalysis Kinetics
Content Type	Text
Resource Type	Article
Subject	Environmental Chemistry Health, Toxicology and Mutagenesis

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