Click for PET: rapid preparation of [18F]fluoropeptides using CuI catalyzed 1,3-dipolar cycloaddition

Jan Marik; Julie Sutcliffe

doi:10.1016/j.tetlet.2006.06.176

Click for PET: rapid preparation of [¹⁸F]fluoropeptides using Cu^I catalyzed 1,3-dipolar cycloaddition

Jan Marik, Julie Sutcliffe

Hematology and Oncology

Research output: Contribution to journal › Article

183 Scopus citations

Abstract

Cu^I catalyzed 1,3-dipolar cycloaddition 'click chemistry' was used to prepare ¹⁸F-radiolabeled peptides. Three ω-[¹⁸F]fluoroalkynes were prepared in yields ranging from 36% to 81%. Conjugation of ω-[¹⁸F]fluoroalkynes to various peptides decorated with 3-azidopropionic acid via Cu^I mediated 1,3-dipolar cycloaddition yielded the desired ¹⁸F-labeled products in 10 min with yields of 54-99% and excellent radiochemical purity (81-99%). The total synthesis time was 30 min from the end of bombardment.

Original language	English (US)
Pages (from-to)	6681-6684
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.176
State	Published - Sep 11 2006

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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Marik, J., & Sutcliffe, J. (2006). Click for PET: rapid preparation of [¹⁸F]fluoropeptides using Cu^I catalyzed 1,3-dipolar cycloaddition. Tetrahedron Letters, 47(37), 6681-6684. https://doi.org/10.1016/j.tetlet.2006.06.176

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abstract = "CuI catalyzed 1,3-dipolar cycloaddition 'click chemistry' was used to prepare 18F-radiolabeled peptides. Three ω-[18F]fluoroalkynes were prepared in yields ranging from 36% to 81%. Conjugation of ω-[18F]fluoroalkynes to various peptides decorated with 3-azidopropionic acid via CuI mediated 1,3-dipolar cycloaddition yielded the desired 18F-labeled products in 10 min with yields of 54-99% and excellent radiochemical purity (81-99%). The total synthesis time was 30 min from the end of bombardment.",

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AB - CuI catalyzed 1,3-dipolar cycloaddition 'click chemistry' was used to prepare 18F-radiolabeled peptides. Three ω-[18F]fluoroalkynes were prepared in yields ranging from 36% to 81%. Conjugation of ω-[18F]fluoroalkynes to various peptides decorated with 3-azidopropionic acid via CuI mediated 1,3-dipolar cycloaddition yielded the desired 18F-labeled products in 10 min with yields of 54-99% and excellent radiochemical purity (81-99%). The total synthesis time was 30 min from the end of bombardment.

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