Article (Scientific journals)
6-Aminopenicillanic acid (6-APA) derivatives equipped with anchoring arms
Favre, Annaïck; Grugier, Jérôme; Brans, Alain et al.
2012 • In Tetrahedron, 68 (52), p. 10818 - 10826
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Keywords :
β-Lactam antibiotics; β-Lactamases; D,D-Carboxypeptidases; Protein array; Biochemistry; Drug Discovery; Organic Chemistry
Abstract :
[en] 6-APA derivatives were considered as selective labels for the construction of bifunctional linkers dedicated to the oriented immobilization of proteins on materials. Sulbactam-like compounds (i.e., 6-β-sulfonamido-penam sulfones) and penicillin G - like compounds (i.e., para-substituted 6-β- phenylacetamido-penams) were prepared and tested as irreversible inhibitors of representative β-lactamases and D,D-peptidases, respectively. The activity of the modified antibiotics was preserved despite their substitution with various anchoring arms. The (2-nitro-4,5-dimethoxy)-benzyl esters revealed of particular interest due to their capacity to acylate BlaR-CTD without deprotection. © 2012 Elsevier Ltd. All rights reserved.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Favre, Annaïck;  Institute of Condensed Matter and Nanosciences (IMCN), Université Catholique de Louvain, Bâtiment Lavoisier, B-1348 Louvain-la-Neuve, Belgium
Grugier, Jérôme;  Institute of Condensed Matter and Nanosciences (IMCN), Université Catholique de Louvain, Bâtiment Lavoisier, B-1348 Louvain-la-Neuve, Belgium
Brans, Alain  ;  Université de Liège - ULiège > Centres généraux > Centre d'ingénierie des protéines
Joris, Bernard ;  Université de Liège - ULiège > Département des sciences de la vie > Physiologie et génétique bactériennes
Marchand-Brynaert, Jacqueline;  Institute of Condensed Matter and Nanosciences (IMCN), Université Catholique de Louvain, Bâtiment Lavoisier, B-1348 Louvain-la-Neuve, Belgium
Language :
English
Title :
6-Aminopenicillanic acid (6-APA) derivatives equipped with anchoring arms
Publication date :
30 December 2012
Journal title :
Tetrahedron
ISSN :
0040-4020
Publisher :
Elsevier BV
Volume :
68
Issue :
52
Pages :
10818 - 10826
Peer reviewed :
Peer Reviewed verified by ORBi
Funding text :
This work was supported by the Inter-university Attraction Pole (IAP program P6/19 PROFUSA), the Walloon Government (Waleo 2 program OPARRAY and Waleo 3 program RAPARRAY) and the Fonds de la Recherche Scientifique (F.R.S.-FNRS, Belgium). Ir S. Grubisic is acknowledged for the biological evalutions. J.M.-B. is senior research associate of the F.R.S.-FNRS.
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