Universität zu Köln

Zlatopolskiy, Boris D., Krapf, Philipp, Richarz, Raphael, Frauendorf, Holm, Mottaghy, Felix M. and Neumaier, Bernd ORCID: 0000-0001-5425-3116 (2014). Synthesis of F-18-Labelled beta-Lactams by Using the Kinugasa Reaction. Chem.-Eur. J., 20 (16). S. 4697 - 4704. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

Owing to their broad spectrum of biological activities and low toxicity, -lactams are attractive lead structures for the design of novel molecular probes. However, the synthesis of positron emission tomography (PET)-isotope-labelled -lactams has not yet been reported. Herein, we describe the simple preparation of radiofluorinated -lactams by using the fast Kinugasa reaction between F-18-labelled nitrone [F-18]-1 and alkynes of different reactivity. Additionally, F-18-labelled fused -lactams were obtained through the reaction of a cyclic nitrone 7 with radiofluorinated alkynes [F-18]-6a,b. Radiochemical yields of the Kinugasa reaction products could be significantly increased by the use of different Cu-I ligands, which additionally allowed a reduction in the amount of precursor and/or reaction time. Model radiofluorinated -lactam-peptide and protein conjugates ([F-18]-10 and F-18-labelled BSA conjugate) were efficiently obtained in high yield under mild conditions (aq. MeCN, ambient temperature) within a short reaction time, demonstrating the suitability of the developed method for radiolabelling of sensitive molecules such as biopolymers.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Zlatopolskiy, Boris D. UNSPECIFIED UNSPECIFIED UNSPECIFIED Krapf, Philipp UNSPECIFIED UNSPECIFIED UNSPECIFIED Richarz, Raphael UNSPECIFIED UNSPECIFIED UNSPECIFIED Frauendorf, Holm UNSPECIFIED UNSPECIFIED UNSPECIFIED Mottaghy, Felix M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neumaier, Bernd UNSPECIFIED orcid.org/0000-0001-5425-3116 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-440711
DOI:	10.1002/chem.201304056
Journal or Publication Title:	Chem.-Eur. J.
Volume:	20
Number:	16
Page Range:	S. 4697 - 4704
Date:	2014
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language COPPER-CATALYZED REACTION; CLICK; PET; TRANSPEPTIDASE; CYCLOADDITION; FLUORINATION; INHIBITOR; PYRIDINES; F-18 Multiple languages Chemistry, Multidisciplinary Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/44071