Making a C-F Bond

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Science  27 Apr 2001:
Vol. 292, Issue 5517, pp. 605
DOI: 10.1126/science.292.5517.605b

Naturally fluorinated biomolecules are rare. Although enzymatic reactions in which other halogens are manipulated either in their cationic or radical forms are known, the stability of the fluoride anion and its ready propensity as a leaving group may preclude its incorporation into metabolites. (Its leaving group character has, in fact, been the basis for the design of suicide inhibitors.) Now, Zechel et al. describe the detection by 19F nuclear magnetic resonance of fluorinated glycosides as intermediates generated by two selectively mutated retaining glycosidases. Removal of one of the active site carboxylates enables fluorine to carry out the nucleophilic attack in the first or second step of the double displacement reaction. — GJC

J. Am Chem. Soc., in press.

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