Sequestration of a fluorinated analog of 2,4-dichlorophenol and metabolic products by L. minor as evidenced by 19F NMR

19F NMR applications in chemical biology

“…In concert with the increased interest in preparing fluorinated compounds that have biological effects, has been the technological advancement in the detection of fluorinated compounds. 19 F nuclear magnetic resonance is an invaluable tool for determination of the structure of fluorinated compounds, but the characteristics of 19 F NMR spectra make it very useful to investigate the interaction of fluorinated compounds with biological systems: the sensitivity of the fluorine nucleus is only slightly less than hydrogen, thus it is possible to detect mM concentrations; the resonances of organofluorine compounds do not overlap with those of carbon-13 and hydrogen, accordingly analysis is possible without the need for purification; and the relatively large chemical shifts resulting from minor changes in the chemical environment, such as those occurring during enzyme-catalysed reactions or interactions with other macromolecules, means that there is little or no peak overlap. In this paper, the application of 19 F NMR in aspects of chemical biology is reviewed, with particular emphasis on the monitoring of organofluorine metabolism and the probing of macromolecular interactions.…”

“…The fluorine atom with its relative small size and 100% natural isotope abundance represents an attractive option for biological NMR studies. In this paper we review the recent literature highlighting the exploitation of 19 F NMR in a range of research areas at the interface of chemistry and biology.…”

“…Analysis of organofluorine compounds by 19 F NMR was largely confined to synthetic chemists but this technique is finding increasing applications in biological systems. The fluorine atom with its relative small size and 100% natural isotope abundance represents an attractive option for biological NMR studies.…”

Bioconcentration, Bioaccumulation, and Metabolism of Pesticides in Aquatic Organisms

“…O-and Nmethylation reactions have been commonly observed for phase-I and -II metabolism of nitro, amino, phenol, and carboxylic acid derivatives, but the relevant enzymology is obscure. The successive acylation of glucose conjugation, mainly at 6-O position, is also known to occur in algae and macrophytes (Day and Saunders 2004;Fujisawa et al 2006;Pascal-Lorber et al 2004;Petroutsos et al 2007;Tront and Saunders 2007); this reaction also is catalyzed by acyltransferases.…”

“…More information on glucosidation has been accumulated through studies on the metabolism of phenols, anilines, PAHs, and pesticides in algae (Kneifel et al 1997;Petroutsos et al 2007;Schoeny et al 1988;Schuphan 1974;Soeder et al 1987;Warshawsky et al 1988Warshawsky et al , 1990, aquatic macrophytes (Barber et al 1995;Ben-Tal and Cleland 1982;Day and Saunders 2004;Ensley et al 1994;Fujisawa et al 2006;Nakajima et al 2004;Pascal-Lorber et al 2004;Roy and Hänninen 1994;Sharma et al 1997;Tront and Saunders 2007), crustacea (Foster and Crosby 1986;Johnston and Corbett 1986a, b;Kashiwada et al 1998;Kobayashi et al 1985aKobayashi et al , b, 1990Kukkonen and Oikari 1988;Sanborn and Malins 1980;Schell and James 1989;Takimoto et al 1987b), bivalva (Shofer and Tjeerdema 1993;Takimoto et al 1987a;Tjeerdema and Crosby 1992), and gumboot chiton (Landrum and Crosby 1981). Pridham (1964) first reported the insignificant activity of UDPG transferases in aquatic macrophytes and algae using quinol and resorcinol, while the usage of various substrates has later revealed the wide distribution of O-glucosyltransferases in the soluble enzyme fraction of these species, but with the limited distribution of N-and S-glucosyltransferases (Pflugmacher and Sandermann 1998a;Pflugmacher et al 1999).…”