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Titolo:
Modification and inhibition of vancomycin group antibiotics by formaldehyde and acetaldehyde
Autore:
Heck, AJR; Bonnici, PJ; Breukink, E; Morris, D; Wills, M;
Indirizzi:
Univ Utrecht, Dept Biomol Mass Spectrometry, Bijvoet Ctr Biomol Res, NL-3584 CA Utrecht, Netherlands Univ Utrecht Utrecht Netherlands NL-3584 CA 3584 CA Utrecht, Netherlands Univ Utrecht, Utrecht Inst Pharmaceut Sci, NL-3584 CA Utrecht, NetherlandsUniv Utrecht Utrecht Netherlands NL-3584 CA 3584 CA Utrecht, Netherlands Univ Utrecht, Dept Biochem Membranes, Ctr Biomembranes & Lipid Enzymol, NL-3584 CH Utrecht, Netherlands Univ Utrecht Utrecht Netherlands NL-3584 CH3584 CH Utrecht, Netherlands Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England Univ Warwick Coventry W Midlands England CV4 7AL 7AL, W Midlands, England
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 4, volume: 7, anno: 2001,
pagine: 910 - 916
SICI:
0947-6539(20010216)7:4<910:MAIOVG>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
IONIZATION MASS-SPECTROMETRY; ALANYL-D-ALANINE; GLYCOPEPTIDE ANTIBIOTICS; CAPILLARY ELECTROPHORESIS; BINDING CONSTANTS; MODEL PEPTIDES; DIMERIZATION; AVOPARCIN; COMPLEXES; ANALOGS;
Keywords:
antibiotics; mass spectrometry; natural products; non-covalent complexes; vancomycin;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
38
Recensione:
Indirizzi per estratti:
Indirizzo: Heck, AJR Univ Utrecht, Dept Biomol Mass Spectrometry, Bijvoet Ctr Biomol Res, Sorbonnelaan 16, NL-3584 CA Utrecht, Netherlands Univ Utrecht Sorbonnelaan 16 Utrecht Netherlands NL-3584 CA nds
Citazione:
A.J.R. Heck et al., "Modification and inhibition of vancomycin group antibiotics by formaldehyde and acetaldehyde", CHEM-EUR J, 7(4), 2001, pp. 910-916

Abstract

It is shown that several vancomycin group antibiotics (vancomycin, eremomycin, and avoparcin) undergo spontaneous chemical modifications when kept atroom temperature at neutral pH in aqueous solutions containing traces of formaldehyde or acetaldehyde. This chemical modification predominantly results in a mass increase of 12 Da in the reaction with formaldehyde and 26 Da in the case of acetaldehyde. By using tandem mass spectrometry the modification can unambiguously be identified as originating from the formation of aring-closed 4-imidazolidinone moiety at the N-terminus of the glycopeptideantibiotics, that is, near the receptor binding pocket of the glycopeptideantibiotics. Bioaffinity mass spectrometry shows that this ring-closure results in a dramatically decreased affinity for the peptidoglycan-mimicking D-alanyl-D-alanine receptor. Additionally in vitro inhibition measurements on two different strains of bacteria have revealed that the modified antibiotics display reduced antibacterial activity. The ring-closure is also shown to have a dissociative effect on the dimerization of the vancomycin-analogue eremomycin. The spontaneous reaction of vancomycin with formaldehyde oracetaldehyde may have implications not only for the clinical use of this class of antibiotics, but also for the effectiveness of these antibiotics when they are used in chiral separation chromatography or capillary electrophoresis.

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Documento generato il 05/07/20 alle ore 00:34:51