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.
authors.affiliation: Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Eötvös Loránd University, 1117 Budapest, Hungary. gmezo@elte.hu
authors.forename: Gábor
authors.initials: G
authors.lastname: Mezö
authors.forename: Ildikó
authors.initials: I
authors.lastname: Szabó
authors.forename: István
authors.initials: I
authors.lastname: Kertész
authors.forename: Rózsa
authors.initials: R
authors.lastname: Hegedüs
authors.forename: Erika
authors.initials: E
authors.lastname: Orbán
authors.forename: Ulrike
authors.initials: U
authors.lastname: Leurs
authors.forename: Szilvia
authors.initials: S
authors.lastname: Bösze
authors.forename: Gábor
authors.initials: G
authors.lastname: Halmos
authors.forename: Marilena
authors.initials: M
authors.lastname: Manea
mesh_terms: D000107:Acetylation; D000625:Aminooxyacetic Acid / Q000737:chemistry*; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D003630:Daunorubicin / Q000737:chemistry*; D006801:Humans; D013058:Mass Spectrometry; D015394:Molecular Structure; D013004:Somatostatin / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000625:Aminooxyacetic Acid; D013004:Somatostatin; D003630:Daunorubicin