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

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Standard

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 tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

Mezö, G, Szabó, I, Kertész, I, Hegedüs, R, Orbán, E, Leurs, U, Bösze, S, Halmos, G & Manea, M 2011, 'Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent', Journal of Peptide Science, bind 17, nr. 1, s. 39-46. https://doi.org/10.1002/psc.1294

APA

Mezö, G., Szabó, I., Kertész, I., Hegedüs, R., Orbán, E., Leurs, U., ... Manea, M. (2011). Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent. Journal of Peptide Science, 17(1), 39-46. https://doi.org/10.1002/psc.1294

Vancouver

Mezö G, Szabó I, Kertész I, Hegedüs R, Orbán E, Leurs U o.a. Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent. Journal of Peptide Science. 2011 jan;17(1):39-46. https://doi.org/10.1002/psc.1294

Author

Mezö, Gábor ; Szabó, Ildikó ; Kertész, István ; Hegedüs, Rózsa ; Orbán, Erika ; Leurs, Ulrike ; Bösze, Szilvia ; Halmos, Gábor ; Manea, Marilena. / Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent. I: Journal of Peptide Science. 2011 ; Bind 17, Nr. 1. s. 39-46.

Bibtex

@article{1389e591d7064132beb13e9243358b82,
title = "Efficient synthesis of an (aminooxy) acetylated-somatostatin derivative using (aminooxy)acetic acid as a 'carbonyl capture' reagent",
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.",
author = "G{\'a}bor Mez{\"o} and Ildik{\'o} Szab{\'o} and Istv{\'a}n Kert{\'e}sz and R{\'o}zsa Heged{\"u}s and Erika Orb{\'a}n and Ulrike Leurs and Szilvia B{\"o}sze and G{\'a}bor Halmos and Marilena Manea",
note = "Copyright {\circledC} 2010 European Peptide Society and John Wiley & Sons, Ltd.",
year = "2011",
month = "1",
doi = "10.1002/psc.1294",
language = "English",
volume = "17",
pages = "39--46",
journal = "Journal of Peptide Science",
issn = "1075-2617",
publisher = "JohnWiley & Sons Ltd",
number = "1",

}

RIS

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

VL - 17

SP - 39

EP - 46

JO - Journal of Peptide Science

JF - Journal of Peptide Science

SN - 1075-2617

IS - 1

ER -

ID: 45967553