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Microbial Biotransformations in the Production and Degradation of Fluorinated Pharmaceuticals
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2020
Cormac D. Murphy, Aoife Phelan
In contrast to the variety of anthropogenic organofluorine compounds in existence, naturally produced fluorinated compounds are rare: of the more than 3,000 halometabolites known, only a handful contain fluorine (O’Hagan and Deng, 2015) and their structures are shown in Fig. 4.2. Fluoroacetate is the most common fluorinated natural product and is produced by plants in tropical and subtropical regions. ω-Fluorofatty acids, predominantly ω-fluorooleic acid, have been found in the seeds of Dichapetalum toxicarium and these compounds probably arise from fluoroacetyl CoA as a starter unit in fatty acid biosynthesis. Fluoroacetate is also converted, via fluoroacetyl CoA, to (2R,3R)-2-fluorocitrate, which has been found to occur in some plants and is responsible for fluoroacetate’s toxicity in animals (Chan and O’Hagan, 2012; Carvalho and Oliveira, 2017). Fluorometabolites are also known in Streptomyces bacteria: the anti-trypanosomal agent nucleocidin is produced by Streptomyces calvus, fluoroacetate and 4-fluorothreonine are produced by S. cattleya and (2R, 3S, 4S)-5-fluoro-2,3,4-trihydroxypentanoic acid was identified in the fermentation broth of Streptomyces sp. MA37 (Ma et al., 2015).
Recent Advances in Chemically Modifiable Polyhydroxyalkanoates
Published in Martin Koller, The Handbook of Polyhydroxyalkanoates, 2020
Atahualpa Pinto, Ryan A. Scheel, Christopher T. Nomura
Fluoropolymers are incredibly useful materials that have transformed the fields of polymer chemistry and materials science, with the classic example being that of poly(tetrafluoroethylene) (PTFE) which has extraordinary physical properties [7]. These properties arise from the C-F bond, which is the strongest single bond to carbon that can be made, and the unique electronic interactions that result from the high electronegativity of fluorine [8]. Organofluorine compounds have also been used extensively in the pharmaceutical industry, where substitutions with fluorine often dramatically alter enzymatic interactions [9,10]. This utility is enhanced by the dearth of organofluorine compounds found in nature; very few metabolic pathways exist that can manipulate C-F bonds, and there are a limited number of biologically produced organofluorine structures [11–14].
Common Properties of Chemicals of Concern and Soil Matrices
Published in Cristiane Q. Surbeck, Jeff Kuo, Site Assessment and Remediation for Environmental Engineers, 2021
Cristiane Q. Surbeck, Jeff Kuo
Per- and polyfluoroalkyl substances (PFAS) are synthetic chemicals that repel water or oil. They are often used as a coating in packaging materials that need to stay dry, on materials that can easily get stained, and in nonstick pots and pans. They enter the environment through the manufacturing process and the wear and tear of products that contain them. These chemicals are organofluorine compounds with fluorine atoms attached to an alkyl chain. The most common ones include perfluorooctanoic acid (PFOA) and perfluorooctane sulfonic acid (PFOS).
Analytical and ecotoxicological studies on degradation of fluoxetine and fluvoxamine by potassium ferrate
Published in Environmental Technology, 2019
Przemysław Drzewicz, Agata Drobniewska, Katarzyna Sikorska, Grzegorz Nałęcz-Jawecki
Organofluorine compounds, due to their favorable physicochemical properties and chemical reactivity, enhanced cell membrane permeability as well as enzyme binding and bioavability are widely used in human medicine [1]. High strength of C-F bond and increased oxidative stability of neighboring C–H bonds make these compounds highly stable towards chemical and metabolic transformation. Among organofluorine compounds are chemotherapeutics (fluorouracil), lipid lowering agents (atorvastatin), fluoroquinolone antibiotics (flumequine, ciprofloxacine) and antidepressants (fluoxetine, fluvoxamine), which account for almost 20% of marketed pharmaceuticals. Due to their physicochemical properties, organofluorine pharmaceutical are persistent in environment.