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Synthesis of [18F]FAC using TMSOTf-assisted system

[18F]FAC is a substrate of deoxcytidine kinase (dCK) and has been used to monitor and image expression and activity of dCK in vivo. dCK phosphorylates deoxycytidine and other nucleoside analogs, which has been associated with its function in immune activation. dCK is also an important enzyme required for the activation of nucleoside-based drugs such as gemcitabine. 

 

Conventional synthesis of [18F]FAC involves a multistep reaction via a nucleophilic substitution method used by Wright et al (Wright et al, 1970). This method has setbacks, due to the need for bromination using HBr, of which any excess needs to be carefully dried. This paper discusses an alternative route of [18F]FAC synthesis using FAC from Carbosynth (ND08343), via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-assisted methodology. This method simplifies the reaction to three steps, as there are no requirements for bromination and drying steps. Other benefits of this system include reduced reaction time and high yields comparable to the conventional method. 

 

For further details, please refer to the original paper: Gangangari KK et al, 2018.

 

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