Isonitrile-based multicomponent synthesis of β-amino boronic acids as β-lactamase inhibitors

Bassini, E.; Gazzotti, S.; Sannio, F.; Presti, L. L.; Sgrignani, J.; Docquier, Jean-Denis; Grazioso, G.; Silvani, A.

doi:10.3390/antibiotics9050249

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Article (Scientific journals)

Isonitrile-based multicomponent synthesis of β-amino boronic acids as β-lactamase inhibitors

Bassini, E.; Gazzotti, S.; Sannio, F. et al.

2020 • In Antibiotics, 9 (5), p. 1-21

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https://hdl.handle.net/2268/252535

DOI
10.3390/antibiotics9050249

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Keywords :

Covalent docking; Multicomponent reactions; Article; Enterobacter cloacae; Escherichia coli; Klebsiella pneumoniae; X ray diffraction

Abstract :

[en] The application of various isonitrile-based multicomponent reactions to protected (2-oxoethyl)boronic acid (as the carbonyl component) is described. The Ugi reaction, both in the four components and in the four centers–three components versions, and the van Leusen reaction, proved effective at providing small libraries of MIDA-protected β-aminoboronic acids. The corresponding free β-aminoboronic acids, quantitatively recovered through basic mild deprotection, were found to be quite stable and were fully characterized, including by11B-NMR spectroscopy. Single-crystal X-ray diffraction analysis, applied both to a MIDA-protected and a free β-aminoboronic acid derivative, provided evidence for different conformations in the solid-state. Finally, the antimicrobial activities of selected compounds were evaluated by measuring their minimal inhibitory concentration (MIC) values, and the binding mode of the most promising derivative on OXA-23 class D β-lactamase was predicted by a molecular modeling study. © 2020 by the authors.

Disciplines :

Microbiology
Biochemistry, biophysics & molecular biology
Physical, chemical, mathematical & earth Sciences: Multidisciplinary, general & others

Author, co-author :

Bassini, E.; Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milan, 20133, Italy

Gazzotti, S.; Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milan, 20133, Italy

Sannio, F.; Dipartimento di Biotecnologie Mediche, Università degli Studi di Siena, Viale Bracci 16, Siena, 53100, Italy

Presti, L. L.; Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milan, 20133, Italy

Sgrignani, J.; Istituto di Ricerca in Biomedicina (IRB), Università della Svizzera Italiana (USI), Via V. Vela 6, Bellinzona, CH-6500, Switzerland

Docquier, Jean-Denis ; Université de Liège - ULiège > Département des sciences de la vie > Centre d'ingénierie des protéines

Grazioso, G.; Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via L. Mangiagalli 25, Milan, 20133, Italy

Silvani, A.; Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milan, 20133, Italy

Language :

English

Title :

Isonitrile-based multicomponent synthesis of β-amino boronic acids as β-lactamase inhibitors

Publication date :

2020

Journal title :

Antibiotics

eISSN :

2079-6382

Publisher :

MDPI AG

Special issue title :

Targeting β-lactamases to Fight Bacterial Resistance to β-lactam Antibiotics

Volume :

Issue :

Pages :

1-21

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 13 November 2020

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