Synthesis of D-Ala--D-Ala Analogues with Postulated Antibacterial Activity.
نویسندگان
چکیده
منابع مشابه
Mutational analysis of active-site residues of the enterococcal D-ala-D-Ala dipeptidase VanX and comparison with Escherichia coli D-ala-D-Ala ligase and D-ala-D-Ala carboxypeptidase VanY.
BACKGROUND Vancomycin-resistant enterococci are pathogenic bacteria that attenuate antibiotic sensitivity by producing peptidoglycan precursors that terminate in D-Ala-D-lactate rather than D-Ala-D-Ala. A key enzyme in effecting antibiotic resistance is the metallodipeptidase VanX, which reduces the cellular pool of the D-Ala-D-Ala dipeptide. RESULTS We constructed eleven mutants, using the r...
متن کاملChapter 771 Actinomadura R39 d-Ala d Ala Carboxypeptidase
bacterial penicillin-binding proteins and beta-lactamases. Antimicrob. Agents Chemother. 42(1), 1 17. [41] Davies, C., White, S.W., Nicholas, R.A. (2001). Crystal structure of a deacylation-defective mutant of penicillin-binding protein 5 at 2.3-Å resolution. J. Biol. Chem. 276(1), 616 623. [42] Nicola, G., Tomberg, J., Pratt, R.F., Nicholas, R.A., Davies, C. (2010). Crystal structures of coval...
متن کاملTight Binding of a Dimeric Derivative of Vancomycin with Dimeric L-Lys-D-Ala-D-Ala
The ligand/receptor pair consisting of a synthetic dimeric derivative of vancomycin (V), linked at the C terminus by p-xylylenediamine (V-CONHCH2C6H4CH2NHCO-V), and a dimeric derivative of L-Lys-D-Ala-D-Ala, [CH2CON H(N-Ac)-L-Lys-D-Ala-D-Ala-CO2]2, provides a new system with which to study the influence of divalency on the strength of binding. A competitive assay using affinity capillary electr...
متن کاملTotal Synthesis of [Ψ[C(=NH)NH]Tpg4]Vancomycin and its (4-Chlorobiphenyl)methyl Derivative: Impact of Peripheral Modifications on Vancomycin Analogues Redesigned for Dual d-Ala-d-Ala and d-Ala-d-Lac Binding
The total synthesis of two key analogues of vancomycin containing single-atom exchanges in the binding pocket (residue 4 amidine and thioamide) are disclosed as well as their peripherally modified (4-chlorobiphenyl)methyl (CBP) derivatives. Their assessment indicates that combined pocket amidine and CBP peripherally modified analogues exhibit a remarkable spectrum of antimicrobial activity (VSS...
متن کاملVancomycin resistance in enterococci: reprogramming of the D-ala-D-Ala ligases in bacterial peptidoglycan biosynthesis.
Vancomycin binds to bacterial cell-wall intermediates to achieve its antibiotic effect. Infections of vancomycin-resistant enterococci are, however, becoming an increasing problem; the bacteria are resistant because they synthesize different cell-wall intermediates. The enzymes involved in cell-wall biosynthesis, therefore, are potential targets for combating this resistance. Recent biochemical...
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ژورنال
عنوان ژورنال: Acta Chemica Scandinavica
سال: 1984
ISSN: 0904-213X
DOI: 10.3891/acta.chem.scand.38b-0647