5 -Fluoro-5 -deoxyadenosine formation

L. Martarello, C. Schaffrath, H. Deng, A.D. Gee, A. Lockhart, D. O Hagan, The first enzymatic method for C-F-18 bond formation The synthesis of 5 -[F-18]-fluoro-5 -deoxyadenosine for imaging with PET, J. Label. Compds Radiopharm. 46 (2003) 1181-1189. 

Finally, recent developments on research into the first C-F bond forming enzyme are summarized. The fluorinase enzyme isolated from Streptomyces cat-tleya catalyzes the formation of 5 -fluoro-5 -deoxyadenosine from S-adenosyl-L-methionine and fluoride. The substrate specificity and subsequent transformation of the fluorinated nucleoside to fluoroacetic acid and to fluoro threonine are discussed. 

The enzyme 5 -fluoro-5 -deoxyadenosine synthetase (5 -FDAS), utilizing SAM, catalyzes the formation of carbon-fluoride bonds. In fact, in presence of F , an 8 2 substitution of methionine at SAM generates the intermediate 5 -fluoro-5 -deoxyadenosine, which is subsequently converted to fluoroacetate and 4-fluorothreonine, whereas in the biosynthesis of salinosporamide A the enzyme achieves the chlorination step through the conversion to 5 -chloro-5 -deoxyadenosine (Section 4.2.2) (Figure 1.61) [51],... 

Fluorination of organic compounds using fluoride ion can be catalyzed by enzymes (Fig. 10.38). For example, fluorinase from Streptomyces cattleya catalyzes C—F bond formation in the reaction of S-adenosyl-L-methionine with fluoride to yield 5 -fluoro-5 -deoxyadenosine. " Although their substrate scope is hmited at present, these kinds of enzymes may come to play an important role for fluorination in the future due to the ease, mildness and safety of the reaction conditions and the use of fluoride as fluorine source. 

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