Stereocontrolled [11C]Alkylation of N-Terminal Glycine Schiff Bases To Obtain Dipeptides

Ulrike Filp*, Aleksandra Pekošak, Alex J. Poot, Albert D. Windhorst

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review


The use of various quaternary ammonium salts as chiral phase-transfer catalysts allowed effective and stereoselective radiochemical [11C]alkylation to obtain functionalized dipeptides. We herein report a broadly applicable procedure for the asymmetric [11C]alkylation of dipeptides to give labeled N-terminal peptides by using different [11C]alkyl halides. Contended stereoselectivities of the reactions were observed by using 11C-labeled alkyl halides, [11C]methyl iodide and [11C]benzyl iodide, and diastereomeric ratios with different specialized catalysts of 95:5 and 90:10 were achieved, respectively. Accordingly, the straightforward synthesis of enantioenriched compounds should play a vital role in peptide-based radiopharmaceutical development and positron emission tomography imaging.

Original languageEnglish
Pages (from-to)5592-5596
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number37
Publication statusPublished - 10 Oct 2017

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