Efficient synthesis of (2S)-tert-butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate as a precursor of PET radiotracer [¹⁸F]FPGLN

ABSTRACT

This study describes a convenient protocol for the synthesis of (2S)-tert-butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate, which can serve as an appropriate precursor of (2S)-5-amino-2-(2-[¹⁸F]fluoropropanamido)-5-oxopentanoic acid (N-(2-[¹⁸F]fluoropropionyl)-L-glutamine, [¹⁸F]FPGLN) for tumor positron emission tomography imaging. Five-step synthesis starting from L-glutamine provided the desired precursor with high yields. In addition, a simple method for the preparation of [¹⁸F]FPGLN from this easily available precursor was developed using a two-step ¹⁸F-labeling strategy.

GRAPHICAL ABSTRACT

KEYWORDS:

• Glutamine derivatives
• new precursor
• positron emission tomography
• radiotracer

Acknowledgments

This work was supported in part by the National Natural Science Foundation of China (Nos. 81571704, 81371584, 81671719), the Science and Technology Foundation of Guangdong Province (Nos. 2014A020210008, 2013B021800264, 2016B090920087), the Science and Technology Planning Project Foundation of Guangzhou (Nos. 201510010145, 201604020169), and the Natural Science Foundation of Guangdong Province (No. 2015A030313067).