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

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

Research output: Contribution to journalArticle

26 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)39-46
Number of pages8
JournalJournal of Peptide Science
Volume17
Issue number1
DOIs
Publication statusPublished - Jan 1 2011

Keywords

  • (aminooxy)acetic acid
  • Carbonyl capture reagent
  • Chemical ligation
  • Drug targeting
  • Oxime bond formation
  • Peptide conjugates
  • Somatostatin

ASJC Scopus subject areas

  • Structural Biology
  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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