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First Fluorinase Enzyme Discovered
STEVE RITTER
Fluorine is the most chemically reactive of all the elements. The flip side to that property is that fluorine forms extremely stable compounds. For example, even though fluorine is the most abundant halogen in Earth's crust, most of the element is tied up in insoluble fluoride minerals. That means naturally occurring organofluorine compounds are rare--only 12 have been discovered--and how these compounds are biosynthesized is largely unknown.
Chemistry professor David O'Hagan and graduate student Christoph Schaffrath of the University of St. Andrews, in Scotland, and coworkers have now found a clue by uncovering the first known fluorinase enzyme [Nature, 416, 279 (2002)]. The researchers show that the fluorinase can catalyze carbon-fluorine bond formation between an organic substrate and fluoride ion.
They studied the enzymatic fluorination by incubating a protein extract from Streptomyces cattleya with potassium fluoride and S-adenosylmethionine (shown). The initial product is 5´-fluoro-5´-deoxyadenosine, which is further converted by other enzymes to fluoroacetate, FCH2CO2–. Fluoroacetate, which has been identified in more than 40 plant species, is the most ubiquitous of the known natural organofluorine compounds.
Although chemists have developed a number of synthetic strategies to prepare organofluorine compounds, discovery of the fluorinase enzyme "opens up a new biotechnological opportunity," O'Hagan says, and could have broad applications in medicinal chemistry.
Chemical & Engineering News
Copyright © 2002 American Chemical Society |
