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Chemo-enzymatic fluorination of unactivated organic compounds

Summary: Chemo-enzymatic fluorination of
unactivated organic compounds
Andrea Rentmeister1, Frances H Arnold1 & Rudi Fasan1,2
Fluorination has gained an increasingly important role in drug
discovery and development. Here we describe a versatile
strategy that combines cytochrome P450­catalyzed
oxygenation with deoxofluorination to achieve mono- and
polyfluorination of nonreactive sites in a variety of organic
scaffolds. This procedure was applied for the rapid
identification of fluorinated drug derivatives with enhanced
membrane permeability.
Fluorination has become an increasingly important tool for fine-
tuning the pharmacokinetic and pharmacological properties of drugs
and lead compounds, thus leading to a growing number of fluorine-
containing pharmaceuticals on the market1. Benefits of hydrogen-
to-fluorine substitutions arise principally from their effects on
membrane permeability, metabolic stability and/or receptor-binding
properties of bioactive molecules1­3. In many cases, fluorination of
much less active precursors has yielded potent drugs with enhanced
bioavailability, reduced toxicity or improved affinity for the target


Source: Arnold, Frances H. - Division of Chemistry and Chemical Engineering, California Institute of Technology


Collections: Chemistry; Biology and Medicine