Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent

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Gábor Mezö, Ildikó Szabó, István Kertész, Rózsa Hegedüs, Erika Orbán, Ulrike Leurs, Szilvia Bösze, Gábor Halmos, Marilena Manea

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.
OriginalsprogEngelsk
TidsskriftJournal of Peptide Science
Vol/bind17
Udgave nummer1
Sider (fra-til)39-46
Antal sider8
ISSN1075-2617
DOI
StatusUdgivet - jan. 2011
Eksternt udgivetJa

ID: 45967553