Chemoselective 18F-incorporation into pyridyl acyltrifluoroborates for rapid radiolabelling of peptides and proteins at room temperature

Aristeidis Chiotellis; Hazem Ahmed; Thomas Betzel; Matthias Tanriver; Christopher J. White; Haewon Song; Sara Da Ros; Roger Schibli; Jeffrey W. Bode; Simon M. Ametamey

doi:10.1039/C9CC08645E

Chemoselective ¹⁸F-incorporation into pyridyl acyltrifluoroborates for rapid radiolabelling of peptides and proteins at room temperature†

Aristeidis Chiotellis,‡^a Hazem Ahmed,

‡^a Thomas Betzel,^a Matthias Tanriver,^b Christopher J. White,^b Haewon Song,^b Sara Da Ros,^b Roger Schibli,

^a Jeffrey W. Bode

*^b and Simon M. Ametamey

*^a

Author affiliations

* Corresponding authors

^a Center for Radiopharmaceutical Sciences ETH-PSI-USZ, Institute of Pharmaceutical Sciences ETH, Vladimir-Prelog-Weg 4, 8093 Zurich, Switzerland
E-mail: simon.ametamey@pharma.ethz.ch

^b Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, Vladimir-Prelog-Weg 3, 8093 Zurich, Switzerland
E-mail: bode@org.chem.ethz.ch

Abstract

A new prosthetic group is reported for ¹⁸F-labelling of peptides and proteins based on the chemoselective ligation of potassium acyltrifluoroborates (KATs) and hydroxylamines without any detectable ¹⁸F/¹⁹F isotope exchange at the acyltrifluoroborate moiety. The new building block is appended via a common amide bond at room temperature with no need for protecting groups which enables an effective orthogonal ¹⁸F-radiolabelling.

Chemical Communications

Chemoselective ¹⁸F-incorporation into pyridyl acyltrifluoroborates for rapid radiolabelling of peptides and proteins at room temperature†

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Chemoselective ¹⁸F-incorporation into pyridyl acyltrifluoroborates for rapid radiolabelling of peptides and proteins at room temperature

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