Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent
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Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent. / Mezö, Gábor; Szabó, Ildikó; Kertész, István; Hegedüs, Rózsa; Orbán, Erika; Leurs, Ulrike; Bösze, Szilvia; Halmos, Gábor; Manea, Marilena.
I: Journal of Peptide Science, Bind 17, Nr. 1, 01.2011, s. 39-46.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › fagfællebedømt
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TY - JOUR
T1 - Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent
AU - Mezö, Gábor
AU - Szabó, Ildikó
AU - Kertész, István
AU - Hegedüs, Rózsa
AU - Orbán, Erika
AU - Leurs, Ulrike
AU - Bösze, Szilvia
AU - Halmos, Gábor
AU - Manea, Marilena
N1 - Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd.
PY - 2011/1
Y1 - 2011/1
N2 - 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.
AB - 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.
U2 - 10.1002/psc.1294
DO - 10.1002/psc.1294
M3 - Journal article
C2 - 20812368
VL - 17
SP - 39
EP - 46
JO - Journal of Peptide Science
JF - Journal of Peptide Science
SN - 1075-2617
IS - 1
ER -
ID: 45967553