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“Click Labeling” with 2-[18F]Fluoroethylazide for Positron Emission Tomography
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    “Click Labeling” with 2-[18F]Fluoroethylazide for Positron Emission Tomography
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    Hammersmith Imanet Ltd, Cyclotron Building, Du Cane Road, London W12 ONN, U.K.  Received September 29, 2006
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2007, 18, 3, 989–993
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    https://doi.org/10.1021/bc060301j
    Published April 13, 2007
    Copyright © 2007 American Chemical Society

    Abstract

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    As an effort in the development of more flexible 18F-labeling chemistry, we report herein on the use of the Cu(I)-catalyzed Huisgen cycloaddition, also known as the “click reaction”, to form 18F-labeled 1,2,3-triazoles. Nucleophilic fluorination of 2-azidoethyl-4-toluenesulfonate followed by distillation provided 2-[18F]fluoroethylazide in 55% radiochemical yield (decay-corrected). 2-[18F]fluoroethylazide was reacted with a small library of terminal alkynes in the presence of excess Cu2+/ascorbate or copper powder. The most reactive alkyne, N-benzylpropynamide provided nearly quantitative incorporation of 2-[18F]fluoroethylazide after 15 min at ambient temperature, whereas the majority of the alkyne substrates provided excellent yields of the corresponding 18F-labeled 1,2,3-triazoles following heating to 80 °C. Using the method described, a model peptide was obtained in 92.3 ± 0.3% (n = 3) radiochemical yield (decay-corrected) after purification by semipreparative HPLC.

    Copyright © 2007 American Chemical Society

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     Erik Årstad, E-mail:  [email protected], Tel. +44 208 383 3714, Fax +44 208 383 8573.

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    HPLC chromatograms of reference compounds and 18F-labeled derivatives. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2007, 18, 3, 989–993
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    https://doi.org/10.1021/bc060301j
    Published April 13, 2007
    Copyright © 2007 American Chemical Society

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