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A Localized Tolerance in the Substrate Specificity of the Fluorinase Enzyme enables "Last-Step" F-18 Fluorination of a RGD Peptide under Ambient Aqueous Conditions

Author(s): S. Thompson, Q. Z. Zhang, M. Onega, S. McMahon, I. Fleming, S. Ashworth, J. H. Naismith, J. Passchier, D. O. Hagan

Abstract:
A strategy for last-step F-18 fluorination of bioconjugated peptides is reported that exploits an "Achilles heel" in the substrate specificity of the fluorinase enzyme. An acetylene functionality at the C-2 position of the adenosine substrate projects from the active site into the solvent. The fluorinase catalyzes a transhalogenation of 5'-chlorodeoxy-2-ethynyladenosine (CID EA) to 5'-fluorodeoxy-2-ethynyladenosine (FDEA). Extending a polyethylene glycol linker from the terminus of the acetylene allows the presentation of bioconjugation cargo to the enzyme for F-18 labelling. The method uses an aqueous solution ((H2O)-O-18) of [F-18]fluoride generated by the cyclotron and has the capacity to isotopically label peptides of choice for positron emission tomography (PET).

Full version: Available here

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ISBN: 1433-7851
Publication Year: 2014
Periodical: Angewandte Chemie-International Edition
Periodical Number: 34
Volume: 53
Pages: 8913-8918
Author Address: Hagan, DO Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland Univ London Imperial Coll Sci Technol & Med, Hammersmith Hosp, Imanova, London W12 0NN, England Univ Aberdeen, Sch Med & Dent, Aberdeen Biomed Imaging Ctr, Aberdeen AB25 2ZD, Scotland