Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties

Lee, Ting-Wai; Verhey, Theodore B.; Antiperovitch, Pavel A.; Atamanyuk, Dmytro; Desroy, Nicolas; Oliveira, Chrystelle; Denis, Alexis; Gerusz, Vincent; Drocourt, Elodie; Loutet, Slade A.; Hamad, Mohamad A.; Stanetty, Christian; Andres, Sara N.; Sugiman-Marangos, Seiji; Kosma, Paul; Valvano, Miguel A.; Moreau, Francois; Junop, Murray S.

doi:10.1021/jm301483h

Title: Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties

Authors:

Lee, Ting-Wai ^[1]; Verhey, Theodore B. ^[1]; Antiperovitch, Pavel A. ^[1]; Atamanyuk, Dmytro ^[2]; Desroy, Nicolas ^[2]; Oliveira, Chrystelle ^[2]; Denis, Alexis ^[2]; Gerusz, Vincent ^[2]; Drocourt, Elodie ^[2]; Loutet, Slade A. ^[3]; Hamad, Mohamad A. ^[3]; Stanetty, Christian ^[4]; Andres, Sara N. ^[1]; Sugiman-Marangos, Seiji ^[1]; Kosma, Paul ^[4]; Valvano, Miguel A. ^[5]; Moreau, Francois ^[2]; Junop, Murray S. ^[1]

Department of Biochemistry and Biomedical Sciences and Michael G. DeGroote Institute for Infectious Disease Research, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4K1, Canada
MUTABILIS, 102 Avenue Gaston Roussel, 93230 Romainville, France
Centre for Human Immunology, Department of Microbiology and Immunology, Western University, London, Ontario, N6A 5C1, Canada
Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria
Centre for Human Immunology, Department of Microbiology and Immunology, Western University, London, Ontario, N6A 5C1, Canada, Centre for Infection and Immunity, Queen’s University of Belfast, Belfast BT9 7BL, United Kingdom

Publication Date:: Tue Jan 22 00:00:00 EST 2013

Sponsoring Org.:: USDOE

OSTI Identifier:: 1123344

Resource Type:: Published Article

Journal Name:: Journal of Medicinal Chemistry

Additional Journal Information:: Journal Name: Journal of Medicinal Chemistry Journal Volume: 56 Journal Issue: 4; Journal ID: ISSN 0022-2623

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Citation Formats


                    Lee, Ting-Wai, Verhey, Theodore B., Antiperovitch, Pavel A., Atamanyuk, Dmytro, Desroy, Nicolas, Oliveira, Chrystelle, Denis, Alexis, Gerusz, Vincent, Drocourt, Elodie, Loutet, Slade A., Hamad, Mohamad A., Stanetty, Christian, Andres, Sara N., Sugiman-Marangos, Seiji, Kosma, Paul, Valvano, Miguel A., Moreau, Francois, and Junop, Murray S. Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties.  United States: N. p., 2013. 
Web.  doi:10.1021/jm301483h.

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                    Lee, Ting-Wai, Verhey, Theodore B., Antiperovitch, Pavel A., Atamanyuk, Dmytro, Desroy, Nicolas, Oliveira, Chrystelle, Denis, Alexis, Gerusz, Vincent, Drocourt, Elodie, Loutet, Slade A., Hamad, Mohamad A., Stanetty, Christian, Andres, Sara N., Sugiman-Marangos, Seiji, Kosma, Paul, Valvano, Miguel A., Moreau, Francois, & Junop, Murray S. Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties.  United States.  https://doi.org/10.1021/jm301483h

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                    Lee, Ting-Wai, Verhey, Theodore B., Antiperovitch, Pavel A., Atamanyuk, Dmytro, Desroy, Nicolas, Oliveira, Chrystelle, Denis, Alexis, Gerusz, Vincent, Drocourt, Elodie, Loutet, Slade A., Hamad, Mohamad A., Stanetty, Christian, Andres, Sara N., Sugiman-Marangos, Seiji, Kosma, Paul, Valvano, Miguel A., Moreau, Francois, and Junop, Murray S. Tue .  
"Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties".  United States.  https://doi.org/10.1021/jm301483h.

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@article{osti_1123344,

  title        = {Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties},

  author       = {Lee, Ting-Wai and Verhey, Theodore B. and Antiperovitch, Pavel A. and Atamanyuk, Dmytro and Desroy, Nicolas and Oliveira, Chrystelle and Denis, Alexis and Gerusz, Vincent and Drocourt, Elodie and Loutet, Slade A. and Hamad, Mohamad A. and Stanetty, Christian and Andres, Sara N. and Sugiman-Marangos, Seiji and Kosma, Paul and Valvano, Miguel A. and Moreau, Francois and Junop, Murray S.},

  abstractNote = {},

  doi          = {10.1021/jm301483h},

  journal      = {Journal of Medicinal Chemistry},

  number       = 4,

  volume       = 56,

  place        = {United States},

  year         = {Tue Jan 22 00:00:00 EST 2013},

  month        = {Tue Jan 22 00:00:00 EST 2013}

}

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Title: Structural–Functional Studies of Burkholderia cenocepacia d -Glycero-β- d -manno-heptose 7-Phosphate Kinase (HldA) and Characterization of Inhibitors with Antibiotic Adjuvant and Antivirulence Properties

Citation Formats

Efficient chemical synthesis of both anomers of ADP l-glycero- and d-glycero-d-manno-heptopyranose journal, November 2003

The crystal structure of ADP-l-glycero-d-mannoheptose 6-epimerase: catalysis with a twist journal, May 2000

New tools for structure refinement in PHENIX journal, August 2010

Bacterial cell wall assembly: still an attractive antibacterial target journal, April 2011

A Complete Lipopolysaccharide Inner Core Oligosaccharide Is Required for Resistance of Burkholderia cenocepacia to Antimicrobial Peptides and Bacterial Survival In Vivo journal, March 2006

An In Vitro Screen of Bacterial Lipopolysaccharide Biosynthetic Enzymes Identifies an Inhibitor of ADP-Heptose Biosynthesis journal, April 2006

Functional Analysis of the glycero-manno -Heptose 7-Phosphate Kinase Domain from the Bifunctional HldE Protein, Which Is Involved in ADP- l - glycero - d - manno -Heptose Biosynthesis journal, August 2005

Dali server: conservation mapping in 3D journal, May 2010

Structural Determinants of Substrate Recognition in the HAD Superfamily Member d - glycero - d - manno -Heptose-1,7-bisphosphate Phosphatase (GmhB), journal, January 2010

Adenosine kinase and ribokinase – the RK family of proteins journal, June 2008

Distributing many points on a sphere journal, December 1997

Structural and Kinetic Characterization of the LPS Biosynthetic Enzyme d -α,β- d -Heptose-1,7-bisphosphate Phosphatase (GmhB) from Escherichia coli , journal, January 2010

Large-Scale Analysis of the Meningococcus Genome by Gene Disruption: Resistance to Complement-Mediated Lysis journal, February 2003

New strategies for combating multidrug-resistant bacteria journal, June 2007

Morphological heterogeneity among Salmonella lipopolysaccharide chemotypes in silver-stained polyacrylamide gels. journal, January 1983

Understanding efflux in Gram-negative bacteria: opportunities for drug discovery journal, May 2012

An expression vector containing a rhamnose-inducible promoter provides tightly regulated gene expression in Burkholderia cenocepacia journal, November 2005

Lipopolysaccharide Endotoxins journal, June 2002

New Targets and Screening Approaches in Antimicrobial Drug Discovery journal, January 2005

Discovery and Development of ATPase Inhibitors of DNA Gyrase as Antibacterial Agents journal, August 2007

The interpretation of protein structures: Estimation of static accessibility journal, February 1971

A system for the construction of targeted unmarked gene deletions in the genus Burkholderia: Targeted unmarked gene deletions in Burkholderia journal, March 2008

Genetic organization of the O7-specific lipopolysaccharide biosynthesis cluster of Escherichia coli VW187 (O7:K1) The GenBank accession number for the DNA sequence reported in this paper is AF125322. journal, September 1999

Multidrug Resistance in Bacteria journal, June 2009

New Targets for Antibacterial Design: Kdo Biosynthesis and LPS Machinery Transport to the Cell Surface journal, February 2011

Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides journal, July 2002

Convergent evolution of similar enzymatic function on different protein folds: The hexokinase, ribokinase, and galactokinase families of sugar kinases journal, January 1993

PDBsum new things journal, January 2009

The Structure of Sedoheptulose-7-Phosphate Isomerase from Burkholderia pseudomallei Reveals a Zinc Binding Site at the Heart of the Active Site journal, July 2010

Outer membrane permeability barrier to azithromycin, clarithromycin, and roxithromycin in gram-negative enteric bacteria. journal, February 1993

Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase journal, February 2009

Systematic Synthesis of Inhibitors of the Two First Enzymes of the Bacterial Heptose Biosynthetic Pathway: Towards Antivirulence Molecules Targeting Lipopolysaccharide Biosynthesis journal, August 2011

[20] Processing of X-ray diffraction data collected in oscillation mode book, January 1997

Molecular basis of bacterial outer membrane permeability journal, March 1985

Biosynthesis Pathway of ADP-L-glycero- -D-manno-Heptose in Escherichia coli journal, January 2002

Efficient chemical synthesis of both anomers of ADP l-glycero- and d-glycero-d-manno-heptopyranose
journal, November 2003

The crystal structure of ADP-l-glycero-d-mannoheptose 6-epimerase: catalysis with a twist
journal, May 2000

New tools for structure refinement in PHENIX
journal, August 2010

Bacterial cell wall assembly: still an attractive antibacterial target
journal, April 2011

A Complete Lipopolysaccharide Inner Core Oligosaccharide Is Required for Resistance of Burkholderia cenocepacia to Antimicrobial Peptides and Bacterial Survival In Vivo
journal, March 2006

An In Vitro Screen of Bacterial Lipopolysaccharide Biosynthetic Enzymes Identifies an Inhibitor of ADP-Heptose Biosynthesis
journal, April 2006

Functional Analysis of the glycero-manno -Heptose 7-Phosphate Kinase Domain from the Bifunctional HldE Protein, Which Is Involved in ADP- l - glycero - d - manno -Heptose Biosynthesis
journal, August 2005

Dali server: conservation mapping in 3D
journal, May 2010

Structural Determinants of Substrate Recognition in the HAD Superfamily Member d - glycero - d - manno -Heptose-1,7-bisphosphate Phosphatase (GmhB),
journal, January 2010

Adenosine kinase and ribokinase – the RK family of proteins
journal, June 2008

Distributing many points on a sphere
journal, December 1997

Structural and Kinetic Characterization of the LPS Biosynthetic Enzyme d -α,β- d -Heptose-1,7-bisphosphate Phosphatase (GmhB) from Escherichia coli ,
journal, January 2010

Large-Scale Analysis of the Meningococcus Genome by Gene Disruption: Resistance to Complement-Mediated Lysis
journal, February 2003

New strategies for combating multidrug-resistant bacteria
journal, June 2007

Morphological heterogeneity among Salmonella lipopolysaccharide chemotypes in silver-stained polyacrylamide gels.
journal, January 1983

Understanding efflux in Gram-negative bacteria: opportunities for drug discovery
journal, May 2012

An expression vector containing a rhamnose-inducible promoter provides tightly regulated gene expression in Burkholderia cenocepacia
journal, November 2005

Lipopolysaccharide Endotoxins
journal, June 2002

New Targets and Screening Approaches in Antimicrobial Drug Discovery
journal, January 2005

Discovery and Development of ATPase Inhibitors of DNA Gyrase as Antibacterial Agents
journal, August 2007

The interpretation of protein structures: Estimation of static accessibility
journal, February 1971

A system for the construction of targeted unmarked gene deletions in the genus Burkholderia: Targeted unmarked gene deletions in Burkholderia
journal, March 2008

Genetic organization of the O7-specific lipopolysaccharide biosynthesis cluster of Escherichia coli VW187 (O7:K1) The GenBank accession number for the DNA sequence reported in this paper is AF125322.
journal, September 1999

Multidrug Resistance in Bacteria
journal, June 2009

New Targets for Antibacterial Design: Kdo Biosynthesis and LPS Machinery Transport to the Cell Surface
journal, February 2011

Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides
journal, July 2002

Convergent evolution of similar enzymatic function on different protein folds: The hexokinase, ribokinase, and galactokinase families of sugar kinases
journal, January 1993

PDBsum new things
journal, January 2009

The Structure of Sedoheptulose-7-Phosphate Isomerase from Burkholderia pseudomallei Reveals a Zinc Binding Site at the Heart of the Active Site
journal, July 2010

Outer membrane permeability barrier to azithromycin, clarithromycin, and roxithromycin in gram-negative enteric bacteria.
journal, February 1993

Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase
journal, February 2009

Systematic Synthesis of Inhibitors of the Two First Enzymes of the Bacterial Heptose Biosynthetic Pathway: Towards Antivirulence Molecules Targeting Lipopolysaccharide Biosynthesis
journal, August 2011

[20] Processing of X-ray diffraction data collected in oscillation mode
book, January 1997

Molecular basis of bacterial outer membrane permeability
journal, March 1985

Biosynthesis Pathway of ADP-L-glycero- -D-manno-Heptose in Escherichia coli
journal, January 2002