Efficient synthesis of an (aminooxy) acetylated‐somatostatin derivative using (aminooxy)acetic acid as a ‘carbonyl capture’ reagent |
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| Authors: | Gábor Mezö Ildikó Szabó István Kertész Rózsa Hegedüs Erika Orbán Ulrike Leurs Szilvia Bösze Gábor Halmos Marilena Manea |
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| Institution: | 1. Research Group of Peptide Chemistry, Hungarian Academy of Sciences, E?tv?s Loránd University, 1117 Budapest, Hungary;2. Institute of Chemistry, E?tv?s Loránd University, 1117 Budapest, Hungary;3. Department of Nuclear Medicine, Medical and Health Science Center, University of Debrecen, 4032 Debrecen, Hungary;4. Laboratory of Analytical Chemistry and Biopolymer Structure Analysis, Department of Chemistry, University of Konstanz, 78457 Konstanz, Germany;5. Department of Biopharmacy, University of Debrecen, 4032 Debrecen, Hungary;6. Zukunftskolleg, University of Konstanz, 78457 Konstanz, Germany |
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| Abstract: | Owing to the high chemoselectivity between an aminooxy function and a carbonyl group, oxime ligation is one of the most preferred procedures for the preparation of peptide conjugates. However, the sensitivity of (aminooxy)acetylated peptides to ketones and aldehydes makes their synthesis and storage difficult. In our study, we established the efficient synthesis of an (aminooxy)acetylated‐somatostatin derivative in the presence of free (aminooxy)acetic acid, which was used as a ‘carbonyl capture’ reagent in the final cleavage step. This (aminooxy)acetylated compound was further used for the chemoselective ligation (oxime bond formation) with daunorubicin and 4‐fluorobenzaldehyde leading to the formation of conjugates with potential applications in targeted cancer chemotherapy and positron emission tomography. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd. |
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| Keywords: | (aminooxy)acetic acid somatostatin chemical ligation oxime bond formation peptide conjugates carbonyl capture reagent drug targeting |
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