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

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2011
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Mező, Gábor
Szabó, Ildikó
Kertész, István
Hegedüs, Rózsa
Orbán, Erika
Bösze, Szilvia
Halmos, Gábor
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Journal of Peptide Science. 2011, 17(1), pp. 39-46. eISSN 1075-2617. Available under: doi: 10.1002/psc.1294
Zusammenfassung

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.

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540 Chemie
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(aminooxy)acetic acid, somatostatin, chemical ligation, oxime bond formation, peptide conjugates, carbonyl capture reagent, drug targeting
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ISO 690MEZŐ, Gábor, Ildikó SZABÓ, István KERTÉSZ, Rózsa HEGEDÜS, Erika ORBÁN, Ulrike LEURS, Szilvia BÖSZE, Gábor HALMOS, Marilena MANEA, 2011. Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent. In: Journal of Peptide Science. 2011, 17(1), pp. 39-46. eISSN 1075-2617. Available under: doi: 10.1002/psc.1294
BibTex
@article{Mezo2011Effic-13593,
  year={2011},
  doi={10.1002/psc.1294},
  title={Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent},
  number={1},
  volume={17},
  journal={Journal of Peptide Science},
  pages={39--46},
  author={Mező, Gábor and Szabó, Ildikó and Kertész, István and Hegedüs, Rózsa and Orbán, Erika and Leurs, Ulrike and Bösze, Szilvia and Halmos, Gábor and Manea, Marilena}
}
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