Inhibition of Escherichia coliGlucosamine-6-phosphate Synthase by Reactive Intermediate Analogues

Bearne, Stephen L.; Blouin, Christian

doi:10.1074/jbc.275.1.135

Cited by 53 publications

(30 citation statements)

References 57 publications

(44 reference statements)

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“…Other glutamine analogues with low micromolar K i values have been synthesized, such as the γ‐dimethylsulfonium derivative (Walker et al , 2000). Some carbohydrate compounds, like 2‐amino‐2‐deoxy‐ d ‐glucitol‐6‐phosphate, have been shown to inhibit the enzyme competitively with respect to fructose‐6‐phosphate (Badet‐Denisot et al , 1995); recently, other carbohydrate‐based inhibitors have been designed as analogues of the reaction intermediates (Bearne & Blouin, 2000). N ‐iodoacetylglucosamine‐6‐phosphate is an active site‐directed irreversible inactivator of GlmS from Escherichia coli , and it interacts with both the sugar‐ and the glucosamine‐binding sites (Bearne, 1996).…”

Section: Biosynthesis Of Udp‐n‐acetylglucosaminementioning

confidence: 99%

Cytoplasmic steps of peptidoglycan biosynthesis

et al. 2008

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The biosynthesis of bacterial cell wall peptidoglycan is a complex process that involves enzyme reactions that take place in the cytoplasm (synthesis of the nucleotide precursors) and on the inner side (synthesis of lipid-linked intermediates) and outer side (polymerization reactions) of the cytoplasmic membrane. This review deals with the cytoplasmic steps of peptidoglycan biosynthesis, which can be divided into four sets of reactions that lead to the syntheses of (1) UDP-N-acetylglucosamine from fructose 6-phosphate, (2) UDP-N-acetylmuramic acid from UDP-N-acetylglucosamine, (3) UDP-N-acetylmuramyl-pentapeptide from UDP-N-acetylmuramic acid and (4) D-glutamic acid and dipeptide D-alanyl-D-alanine. Recent data concerning the different enzymes involved are presented. Moreover, special attention is given to (1) the chemical and enzymatic synthesis of the nucleotide precursor substrates that are not commercially available and (2) the search for specific inhibitors that could act as antibacterial compounds.

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Section: Biosynthesis Of Udp‐n‐acetylglucosaminementioning

confidence: 99%

Cytoplasmic steps of peptidoglycan biosynthesis

et al. 2008

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“…Investigations of the docked conformations of GlcN-6-PS and oxasetin revealed that the NH group at position-1 and the carbonyl group at position-5 of the pyrrole-2,5-dione ring provide sites for receptor interaction by donating and accepting a hydrogen bond with Glu-488 and Ser-401 residues, respectively. Data from the literature also support the amino function as an important moiety to be included in the design of GlcN-6-PS inhibitors [22]. The carbonyl group that connects the octahydronaphthalene and pyrrole-2,5-dione rings of the oxasetin molecule also seems to be important for the binding interaction, as it accepts two hydrogen bonds, each from Thr-302 and Ser-303 ( Figure 5).…”

mentioning

confidence: 90%

Oxasetin from Lophiostoma sp. of the Baltic Sea: Identification, in silico Binding Mode Prediction and Antibacterial Evaluation against Fish Pathogenic Bacteria

Shushni

Azam

Lindequist

2013

Natural Product Communications

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Because of the evolving resistance of microorganisms against existing antibiotics, there is an increasing need for new ones, not only in human, but also in veterinary medicine. The dichloromethane extract of a fungal strain of the genus Lophiostoma, isolated from driftwood collected from the coast of the Baltic Sea, displayed antibacterial activity against some fish pathogenic bacteria. Ergosterol epoxide (1), cerebroside C (2) and oxasetin (3) were isolated from the extract and structurally elucidated on the basis of spectroscopic data and chemical evidence. Compound 3 exhibited in vitro activity against Vibrio anguillarum, Flexibacter maritimus and Pseudomonas anguilliseptica with minimal inhibitory concentrations of 12.5, 12.5 and 6.25 µg/mL, respectively. Molecular docking studies were performed to understand the interaction of compound 3 with different macromolecular targets. Analysis of in silico results, together with experimental findings, validates the antimicrobial activity associated with compound 3. These results may be exploited in lead optimization and development of potent antibacterial agents.

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“…The extensive literature survey and the continuous attempt of our group for exploring novel antimicrobial and antioxidant agents encourages us to synthesize novel series of 2-pyrazoline derivatives containing imine (Schiff base) moiety. The target compounds (3)(4)(5)(6)(7)(8)(9) were prepared and screened against several bacterial species (gram positive and gram negative) and also against Candida albicans. The antioxidant activity of the synthesized derivatives against 2,2-diphenyl-l-picrylhydrazyl (DPPH) radical by the TLC autographic and quantitatively by spectrophotometric assay was achieved.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, Antioxidant and Docking Study of Some Novel 3,5-Disubstituted-4,5-dihydro-1H-pyrazoles Incorporating Imine Moiety

et al. 2018

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A NOVEL series of 3,5-Disubstituted-4,5-Dihydro-1H-pyrazoles (3-9) containing imine moiety were synthesized and characterized using spectral analysis. The synthesized derivatives were In vitro screened against several bacterial species, Staphylococcus aureus, Pseudomonas aeruginosa and Acinetobacterbaumannii as well as Candida albicans and revealed moderate to potent activity. The antioxidant study was confirmed for the synthesized derivatives against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical qualitatively using TLC technique, and quantitatively by spectrophotometric method. The half maximal inhibitory concentration (IC 50) was calculated for the active compounds (1-5, 8). Docking study for the potent compounds (2 and 4) against glucosamine-6-phosphate synthase, the target enzyme for the antimicrobial agents, was explored to explain the interactions of the discovered hits within the amino acid residues of the enzyme active side. The docking parameters enhanced the activity of new compounds as promising antimicrobial agents.

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Inhibition of Escherichia coliGlucosamine-6-phosphate Synthase by Reactive Intermediate Analogues

Cited by 53 publications

References 57 publications

Cytoplasmic steps of peptidoglycan biosynthesis

Cytoplasmic steps of peptidoglycan biosynthesis

Oxasetin from Lophiostoma sp. of the Baltic Sea: Identification, in silico Binding Mode Prediction and Antibacterial Evaluation against Fish Pathogenic Bacteria

Synthesis, Antimicrobial, Antioxidant and Docking Study of Some Novel 3,5-Disubstituted-4,5-dihydro-1H-pyrazoles Incorporating Imine Moiety

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