Automated Radiosynthesis of cis- and trans-4-[18F]Fluoro-L-proline using [18F]Fluoride

Morgan, T. E.F., Riley, L. M., Tavares, A. A.S. and Sutherland, A. (2021) Automated Radiosynthesis of cis- and trans-4-[18F]Fluoro-L-proline using [18F]Fluoride. Journal of Organic Chemistry, 86(20), pp. 14054-14060. (doi: 10.1021/acs.joc.1c00755) (PMID:33913318) (PMCID:PMC8524414)

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The positron emission tomography imaging agents cis- and trans-4-[18F]fluoro-l-proline are used for the detection of numerous diseases such as pulmonary fibrosis and various carcinomas. These imaging agents are typically prepared by nucleophilic fluorination of 4-hydroxy-l-proline derivatives, with [18F]fluoride, followed by deprotection. Although effective radiofluorination reactions have been developed, the overall radiosynthesis process is suboptimal due to deprotection methods that are performed manually, require multiple steps, or involve harsh conditions. Here we describe the development of two synthetic routes that allow access to precursors, which undergo highly selective radiofluorination reactions and rapid deprotection, under mild acidic conditions. These methods were found to be compatible with automation, avoiding manual handling of radioactive intermediates.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Riley, Miss Leanne and Sutherland, Professor Andrew
Authors: Morgan, T. E.F., Riley, L. M., Tavares, A. A.S., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN (Online):1520-6904
Published Online:29 April 2021
Copyright Holders:Copyright © 2021 The Authors
First Published:First published in Journal of Organic Chemistry 86(20): 14054-14060
Publisher Policy:Reproduced under a Creative Commons licence

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
172865EPSRC DTP 16/17 and 17/18Tania GalabovaEngineering and Physical Sciences Research Council (EPSRC)EP/N509668/1Research and Innovation Services