61093-23-0,MFCD31563661
Catalog No.:AA00EPM1

61093-23-0 | bis(3',5')-cyclic diguanylic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥98%
2 weeks  
$1,414.00   $990.00
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  • Properties
  • Literature
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Technical Information
Catalog Number:
AA00EPM1
Chemical Name:
bis(3',5')-cyclic diguanylic acid
CAS Number:
61093-23-0
Molecular Formula:
C20H24N10O14P2
Molecular Weight:
690.4107
MDL Number:
MFCD31563661
SMILES:
O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]3O[C@H]([C@@H]([C@@H]3OP(=O)(OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O)O)O)n1cnc2c1nc(N)[nH]c2=O
Properties
Computed Properties
 
Complexity:
1340  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
46  
Hydrogen Bond Acceptor Count:
18  
Hydrogen Bond Donor Count:
8  
Isotope Atom Count:
0  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-6.8  

Literature

Title: Hfq-dependent, co-ordinate control of cyclic diguanylate synthesis and catabolism in the plague pathogen Yersinia pestis.

Journal: Molecular microbiology 20121101

Title: Surface sensing and lateral subcellular localization of WspA, the receptor in a chemosensory-like system leading to c-di-GMP production.

Journal: Molecular microbiology 20121101

Title: A novel two-component system PdeK/PdeR regulates c-di-GMP turnover and virulence of Xanthomonas oryzae pv. oryzae.

Journal: Molecular plant-microbe interactions : MPMI 20121001

Title: Structural polymorphism of c-di-GMP bound to an EAL domain and in complex with a type II PilZ-domain protein.

Journal: Acta crystallographica. Section D, Biological crystallography 20121001

Title: Crystallization and preliminary X-ray diffraction studies of Xanthomonas campestris PNPase in the presence of c-di-GMP.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20121001

Title: Nanomolar fluorescent detection of c-di-GMP using a modular aptamer strategy.

Journal: Chemical communications (Cambridge, England) 20120918

Title: Impact of QseBC system in c-di-GMP-dependent quorum sensing regulatory network in a clinical isolate SSU of Aeromonas hydrophila.

Journal: Microbial pathogenesis 20120901

Title: Molecular function and potential evolution of the biofilm-modulating blue light-signalling pathway of Escherichia coli.

Journal: Molecular microbiology 20120901

Title: Crystal structure of a catalytically active GG(D/E)EF diguanylate cyclase domain from Marinobacter aquaeolei with bound c-di-GMP product.

Journal: Journal of structural and functional genomics 20120901

Title: Structures of the PelD cyclic diguanylate effector involved in pellicle formation in Pseudomonas aeruginosa PAO1.

Journal: The Journal of biological chemistry 20120831

Title: The prokaryote messenger c-di-GMP triggers stalk cell differentiation in Dictyostelium.

Journal: Nature 20120830

Title: Identification of ligand analogues that control c-di-GMP riboswitches.

Journal: ACS chemical biology 20120817

Title: A novel capture compound for the identification and analysis of cyclic di-GMP binding proteins.

Journal: Journal of proteomics 20120803

Title: Inside the complex regulation of Pseudomonas aeruginosa chaperone usher systems.

Journal: Environmental microbiology 20120801

Title: Crystallization studies of the murine c-di-GMP sensor protein STING.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20120801

Title: 'Life-style' control networks in Escherichia coli: signaling by the second messenger c-di-GMP.

Journal: Journal of biotechnology 20120731

Title: Synthesis and characterization of a fluorescent analogue of cyclic di-GMP.

Journal: Biochemistry 20120710

Title: Structure of the cytoplasmic region of PelD, a degenerate diguanylate cyclase receptor that regulates exopolysaccharide production in Pseudomonas aeruginosa.

Journal: The Journal of biological chemistry 20120706

Title: Sensing the messenger: the diverse ways that bacteria signal through c-di-GMP.

Journal: Protein science : a publication of the Protein Society 20120701

Title: Light-induced alteration of c-di-GMP level controls motility of Synechocystis sp. PCC 6803.

Journal: Molecular microbiology 20120701

Title: Structure of STING bound to cyclic di-GMP reveals the mechanism of cyclic dinucleotide recognition by the immune system.

Journal: Nature structural & molecular biology 20120701

Title: Structural analysis of the STING adaptor protein reveals a hydrophobic dimer interface and mode of cyclic di-GMP binding.

Journal: Immunity 20120629

Title: Cyclic di-GMP sensing via the innate immune signaling protein STING.

Journal: Molecular cell 20120629

Title: The structural basis for the sensing and binding of cyclic di-GMP by STING.

Journal: Nature structural & molecular biology 20120624

Title: Crystal structures of STING protein reveal basis for recognition of cyclic di-GMP.

Journal: Nature structural & molecular biology 20120624

Title: Engineered allosteric ribozymes that sense the bacterial second messenger cyclic diguanosyl 5'-monophosphate.

Journal: Analytical chemistry 20120605

Title: A full-length bifunctional protein involved in c-di-GMP turnover is required for long-term survival under nutrient starvation in Mycobacterium smegmatis.

Journal: Microbiology (Reading, England) 20120601

Title: Vaccination of mice with recombinant bacille Calmette-Guérin harboring Rv1357c protects similarly to native BCG.

Journal: The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 20120601

Title: The YfiBNR signal transduction mechanism reveals novel targets for the evolution of persistent Pseudomonas aeruginosa in cystic fibrosis airways.

Journal: PLoS pathogens 20120601

Title: Nitric oxide modulates bacterial biofilm formation through a multicomponent cyclic-di-GMP signaling network.

Journal: Molecular cell 20120525

Title: Allosteric tertiary interactions preorganize the c-di-GMP riboswitch and accelerate ligand binding.

Journal: ACS chemical biology 20120518

Title: [Exogenous 3', 5'-cyclic diguanylic acid prevents caries formation in rats].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20120501

Title: Cellular levels and binding of c-di-GMP control subcellular localization and activity of the Vibrio cholerae transcriptional regulator VpsT.

Journal: PLoS pathogens 20120501

Title: You've come a long way: c-di-GMP signaling.

Journal: Current opinion in microbiology 20120401

Title: The orphan histidine protein kinase SgmT is a c-di-GMP receptor and regulates composition of the extracellular matrix together with the orphan DNA binding response regulator DigR in Myxococcus xanthus.

Journal: Molecular microbiology 20120401

Title: Nitric oxide regulation of cyclic di-GMP synthesis and hydrolysis in Shewanella woodyi.

Journal: Biochemistry 20120313

Title: Differential binding of 2'-biotinylated analogs of c-di-GMP with c-di-GMP riboswitches and binding proteins.

Journal: Molecular bioSystems 20120301

Title: A C-di-GMP-proflavine-hemin supramolecular complex has peroxidase activity--implication for a simple colorimetric detection.

Journal: Molecular bioSystems 20120301

Title: One-flask synthesis of cyclic diguanosine monophosphate (c-di-GMP).

Journal: Current protocols in nucleic acid chemistry 20120301

Title: Crystallization and preliminary X-ray diffraction characterization of the XccFimX(EAL)-c-di-GMP and XccFimX(EAL)-c-di-GMP-XccPilZ complexes from Xanthomonas campestris.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20120301

Title: [Activity of cyclic diguanylate (c-di-GMP) in bacteria and the study of its derivatives].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20120301

Title: The extremophile Acidithiobacillus ferrooxidans possesses a c-di-GMP signalling pathway that could play a significant role during bioleaching of minerals.

Journal: Letters in applied microbiology 20120201

Title: A chemical proteomics approach to identify c-di-GMP binding proteins in Pseudomonas aeruginosa.

Journal: Journal of microbiological methods 20120201

Title: Discrete cyclic di-GMP-dependent control of bacterial predation versus axenic growth in Bdellovibrio bacteriovorus.

Journal: PLoS pathogens 20120201

Title: Why do microorganisms produce rhamnolipids?

Journal: World journal of microbiology & biotechnology 20120201

Title: Dynamic energy landscapes of riboswitches help interpret conformational rearrangements and function.

Journal: PLoS computational biology 20120201

Title: Oligomer formation of the bacterial second messenger c-di-GMP: reaction rates and equilibrium constants indicate a monomeric state at physiological concentrations.

Journal: Journal of the American Chemical Society 20120118

Title: Diamidinium and iminium aromatics as new aggregators of the bacterial signaling molecule, c-di-GMP.

Journal: Bioorganic & medicinal chemistry letters 20120115

Title: Structural and biochemical characterization of linear dinucleotide analogues bound to the c-di-GMP-I aptamer.

Journal: Biochemistry 20120110

Title: Synthetic quorum-sensing circuit to control consortial biofilm formation and dispersal in a microfluidic device.

Journal: Nature communications 20120103

Title: Adaptive evolution of the lactose utilization network in experimentally evolved populations of Escherichia coli.

Journal: PLoS genetics 20120101

Title: Transcriptome profiling of a curdlan-producing Agrobacterium reveals conserved regulatory mechanisms of exopolysaccharide biosynthesis.

Journal: Microbial cell factories 20120101

Title: Global regulatory pathways and cross-talk control pseudomonas aeruginosa environmental lifestyle and virulence phenotype.

Journal: Current issues in molecular biology 20120101

Title: Comparative genomics of enterococci: variation in Enterococcus faecalis, clade structure in E. faecium, and defining characteristics of E. gallinarum and E. casseliflavus.

Journal: mBio 20120101

Title: The pyrimidine nucleotide biosynthetic pathway modulates production of biofilm determinants in Escherichia coli.

Journal: PloS one 20120101

Title: Genes that influence swarming motility and biofilm formation in Variovorax paradoxus EPS.

Journal: PloS one 20120101

Title: A phylogenetic analysis of the globins in fungi.

Journal: PloS one 20120101

Title: Core site-moiety maps reveal inhibitors and binding mechanisms of orthologous proteins by screening compound libraries.

Journal: PloS one 20120101

Title: Differential expression of iron acquisition genes by Brucella melitensis and Brucella canis during macrophage infection.

Journal: PloS one 20120101

Title: Quorum sensing modulates colony morphology through alkyl quinolones in Pseudomonas aeruginosa.

Journal: BMC microbiology 20120101

Title: Transcriptional regulation of opaR, qrr2-4 and aphA by the master quorum-sensing regulator OpaR in Vibrio parahaemolyticus.

Journal: PloS one 20120101

Title: Social Behaviours under Anaerobic Conditions in Pseudomonas aeruginosa.

Journal: International journal of microbiology 20120101

Title: Mycobacterium tuberculosis Rv3586 (DacA) is a diadenylate cyclase that converts ATP or ADP into c-di-AMP.

Journal: PloS one 20120101

Title: When ribonucleases come into play in pathogens: a survey of gram-positive bacteria.

Journal: International journal of microbiology 20120101

Title: Comparative genomics reveals adaptation by Alteromonas sp. SN2 to marine tidal-flat conditions: cold tolerance and aromatic hydrocarbon metabolism.

Journal: PloS one 20120101

Title: Different evolutionary modifications as a guide to rewire two-component systems.

Journal: Bioinformatics and biology insights 20120101

Title: Cellulose synthase complexes: composition and regulation.

Journal: Frontiers in plant science 20120101

Title: Engineering microbial consortia to enhance biomining and bioremediation.

Journal: Frontiers in microbiology 20120101

Title: A previously uncharacterized gene stm0551 plays a repressive role in the regulation of type 1 fimbriae in Salmonella enterica serotype Typhimurium.

Journal: BMC microbiology 20120101

Title: Comparative analysis of diguanylate cyclase and phosphodiesterase genes in Klebsiella pneumoniae.

Journal: BMC microbiology 20120101

Title: Enzymatically active and inactive phosphodiesterases and diguanylate cyclases are involved in regulation of Motility or sessility in Escherichia coli CFT073.

Journal: mBio 20120101

Title: Second messenger regulation of biofilm formation: breakthroughs in understanding c-di-GMP effector systems.

Journal: Annual review of cell and developmental biology 20120101

Title: Evidence for cyclic diguanylate as a vaccine adjuvant with novel immunostimulatory activities.

Journal: Cellular immunology 20120101

Title: Rational design of fluorescent biosensor for cyclic di-GMP.

Journal: Chembiochem : a European journal of chemical biology 20111216

Title: N-Acetylglucosamine-dependent biofilm formation in Pectobacterium atrosepticum is cryptic and activated by elevated c-di-GMP levels.

Journal: Microbiology (Reading, England) 20111201

Title: The Pseudomonas aeruginosa sensor RetS switches type III and type VI secretion via c-di-GMP signalling.

Journal: Environmental microbiology 20111201

Title: The structure and inhibition of a GGDEF diguanylate cyclase complexed with (c-di-GMP)(2) at the active site.

Journal: Acta crystallographica. Section D, Biological crystallography 20111201

Title: Inhibition of virulence gene expression in Staphylococcus aureus by novel depsipeptides from a marine photobacterium.

Journal: Marine drugs 20111201

Title: Overlapping and unique contributions of two conserved polysaccharide loci in governing distinct survival phenotypes in Vibrio vulnificus.

Journal: Environmental microbiology 20111101

Title: Mechanism for gene control by a natural allosteric group I ribozyme.

Journal: RNA (New York, N.Y.) 20111101

Title: A multi-repeat adhesin of the phytopathogen, Pectobacterium atrosepticum, is secreted by a Type I pathway and is subject to complex regulation involving a non-canonical diguanylate cyclase.

Journal: Molecular microbiology 20111101

Title: Extracellular nucleases and extracellular DNA play important roles in Vibrio cholerae biofilm formation.

Journal: Molecular microbiology 20111101

Title: Synthesis and characterization of C8 analogs of c-di-GMP.

Journal: Nucleosides, nucleotides & nucleic acids 20111101

Title: STING is a direct innate immune sensor of cyclic di-GMP.

Journal: Nature 20111027

Title: Differential analogue binding by two classes of c-di-GMP riboswitches.

Journal: Journal of the American Chemical Society 20111005

Title: Large-scale production of the immunomodulator c-di-GMP from GMP and ATP by an enzymatic cascade.

Journal: Applied biochemistry and biotechnology 20111001

Title: The CRP/FNR family protein Bcam1349 is a c-di-GMP effector that regulates biofilm formation in the respiratory pathogen Burkholderia cenocepacia.

Journal: Molecular microbiology 20111001

Title: Fitness landscape of antibiotic tolerance in Pseudomonas aeruginosa biofilms.

Journal: PLoS pathogens 20111001

Title: The atypical two-component sensor kinase Lpl0330 from Legionella pneumophila controls the bifunctional diguanylate cyclase-phosphodiesterase Lpl0329 to modulate bis-(3'-5')-cyclic dimeric GMP synthesis.

Journal: The Journal of biological chemistry 20110909

Title: c-di-GMP protects against intranasal Acinetobacter baumannii infection in mice by chemokine induction and enhanced neutrophil recruitment.

Journal: International immunopharmacology 20110901

Title: Modulation of Pseudomonas aeruginosa surface-associated group behaviors by individual amino acids through c-di-GMP signaling.

Journal: Research in microbiology 20110901

Title: c-di-AMP is a new second messenger in Staphylococcus aureus with a role in controlling cell size and envelope stress.

Journal: PLoS pathogens 20110901

Title: Regulatory cohesion of cell cycle and cell differentiation through interlinked phosphorylation and second messenger networks.

Journal: Molecular cell 20110819

Title: The bacterial second messenger c-di-GMP: mechanisms of signalling.

Journal: Cellular microbiology 20110801

Title: MrkH, a novel c-di-GMP-dependent transcriptional activator, controls Klebsiella pneumoniae biofilm formation by regulating type 3 fimbriae expression.

Journal: PLoS pathogens 20110801

Title: Intranasal c-di-GMP-adjuvanted plant-derived H5 influenza vaccine induces multifunctional Th1 CD4+ cells and strong mucosal and systemic antibody responses in mice.

Journal: Vaccine 20110712

Title: The diguanylate cyclase, Rrp1, regulates critical steps in the enzootic cycle of the Lyme disease spirochetes.

Journal: Molecular microbiology 20110701

Title: Cyclic diguanylate turnover mediated by the sole GGDEF/EAL response regulator in Pseudomonas putida: its role in the rhizosphere and an analysis of its target processes.

Journal: Environmental microbiology 20110701

Title: Borrelia burgdorferi requires glycerol for maximum fitness during the tick phase of the enzootic cycle.

Journal: PLoS pathogens 20110701

Title: Conservative change to the phosphate moiety of cyclic diguanylic monophosphate remarkably affects its polymorphism and ability to bind DGC, PDE, and PilZ proteins.

Journal: Journal of the American Chemical Society 20110622

Title: Cyclic di-GMP is essential for the survival of the lyme disease spirochete in ticks.

Journal: PLoS pathogens 20110601

Title: Quorum sensing and c-di-GMP-dependent alterations in gene transcripts and virulence-associated phenotypes in a clinical isolate of Aeromonas hydrophila.

Journal: Microbial pathogenesis 20110501

Title: c-di-GMP can form remarkably stable G-quadruplexes at physiological conditions in the presence of some planar intercalators.

Journal: Chemical communications (Cambridge, England) 20110428

Title: Solution structure of the PilZ domain protein PA4608 complex with cyclic di-GMP identifies charge clustering as molecular readout.

Journal: The Journal of biological chemistry 20110422

Title: Cyclic di-GMP activation of polynucleotide phosphorylase signal-dependent RNA processing.

Journal: Journal of molecular biology 20110415

Title: Thiazole orange-induced c-di-GMP quadruplex formation facilitates a simple fluorescent detection of this ubiquitous biofilm regulating molecule.

Journal: Journal of the American Chemical Society 20110406

Title: GGDEF proteins YeaI, YedQ, and YfiN reduce early biofilm formation and swimming motility in Escherichia coli.

Journal: Applied microbiology and biotechnology 20110401

Title: Interactions of the c-di-GMP riboswitch with its second messenger ligand.

Journal: Biochemical Society transactions 20110401

Title: Engineering a novel c-di-GMP-binding protein for biofilm dispersal.

Journal: Environmental microbiology 20110301

Title: Two-component regulatory systems in Pseudomonas aeruginosa: an intricate network mediating fimbrial and efflux pump gene expression.

Journal: Molecular microbiology 20110301

Title: c-di-GMP turn-over in Clostridium difficile is controlled by a plethora of diguanylate cyclases and phosphodiesterases.

Journal: PLoS genetics 20110301

Title: cAMP, c-di-GMP, c-di-AMP and now cGMP: bacteria use them all!

Journal: Molecular microbiology 20110201

Title: Structural characterization reveals that a PilZ domain protein undergoes substantial conformational change upon binding to cyclic dimeric guanosine monophosphate.

Journal: Protein science : a publication of the Protein Society 20110201

Title: A c-di-GMP effector system controls cell adhesion by inside-out signaling and surface protein cleavage.

Journal: PLoS biology 20110201

Title: Biofilm adherence and detachment pathway elucidated.

Journal: PLoS biology 20110201

Title: Structural basis for c-di-GMP-mediated inside-out signaling controlling periplasmic proteolysis.

Journal: PLoS biology 20110201

Title: Binding of cyclic diguanylate in the non-catalytic EAL domain of FimX induces a long-range conformational change.

Journal: The Journal of biological chemistry 20110128

Title: Efficient enzymatic production of the bacterial second messenger c-di-GMP by the diguanylate cyclase YdeH from E. coli.

Journal: Applied biochemistry and biotechnology 20110101

Title: Interaction of the diguanylate cyclase YdeH of Escherichia coli with 2',(3')-substituted purine and pyrimidine nucleotides.

Journal: The Journal of pharmacology and experimental therapeutics 20110101

Title: Surface sensing in Vibrio parahaemolyticus triggers a programme of gene expression that promotes colonization and virulence.

Journal: Molecular microbiology 20110101

Title: Systematic analysis of cyclic di-GMP signalling enzymes and their role in biofilm formation and virulence in Yersinia pestis.

Journal: Molecular microbiology 20110101

Title: Cyclic diguanylate signaling proteins control intracellular growth of Legionella pneumophila.

Journal: mBio 20110101

Title: Biofilm development on Caenorhabditis elegans by Yersinia is facilitated by quorum sensing-dependent repression of type III secretion.

Journal: PLoS pathogens 20110101

Title: FimL regulates cAMP synthesis in Pseudomonas aeruginosa.

Journal: PloS one 20110101

Title: Comparative study between transcriptionally- and translationally-acting adenine riboswitches reveals key differences in riboswitch regulatory mechanisms.

Journal: PLoS genetics 20110101

Title: iGEMDOCK: a graphical environment of enhancing GEMDOCK using pharmacological interactions and post-screening analysis.

Journal: BMC bioinformatics 20110101

Title: Delicate conformational changes of a protein in the CRP family lead to dramatic functional changes via binding of an alternate secondary messenger molecule.

Journal: Virulence 20110101

Title: Proteome and membrane fatty acid analyses on Oligotropha carboxidovorans OM5 grown under chemolithoautotrophic and heterotrophic conditions.

Journal: PloS one 20110101

Title: Comparative genomics reveals diversity among xanthomonads infecting tomato and pepper.

Journal: BMC genomics 20110101

Title: Differential control of Yersinia pestis biofilm formation in vitro and in the flea vector by two c-di-GMP diguanylate cyclases.

Journal: PloS one 20110101

Title: Pseudomonas aeruginosa: resistance to the max.

Journal: Frontiers in microbiology 20110101

Title: Genome-wide mutagenesis of Xanthomonas axonopodis pv. citri reveals novel genetic determinants and regulation mechanisms of biofilm formation.

Journal: PloS one 20110101

Title: A novel tetrameric PilZ domain structure from xanthomonads.

Journal: PloS one 20110101

Title: Gene regulation in Borrelia burgdorferi.

Journal: Annual review of microbiology 20110101

Title: Comparative analyses imply that the enigmatic Sigma factor 54 is a central controller of the bacterial exterior.

Journal: BMC genomics 20110101

Title: CrdS and CrdA comprise a two-component system that is cooperatively regulated by the Che3 chemosensory system in Myxococcus xanthus.

Journal: mBio 20110101

Title: Small Regulatory RNA and Legionella pneumophila.

Journal: Frontiers in microbiology 20110101

Title: The RelA/SpoT homolog (RSH) superfamily: distribution and functional evolution of ppGpp synthetases and hydrolases across the tree of life.

Journal: PloS one 20110101

Title: An α/β hydrolase and associated Per-ARNT-Sim domain comprise a bipartite sensing module coupled with diverse output domains.

Journal: PloS one 20110101

Title: The structure of an unconventional HD-GYP protein from Bdellovibrio reveals the roles of conserved residues in this class of cyclic-di-GMP phosphodiesterases.

Journal: mBio 20110101

Title: Biosynthesis of the Pseudomonas aeruginosa Extracellular Polysaccharides, Alginate, Pel, and Psl.

Journal: Frontiers in microbiology 20110101

Title: Contribution of TAT system translocated PhoX to Campylobacter jejuni phosphate metabolism and resilience to environmental stresses.

Journal: PloS one 20110101

Title: Escherichia coli BdcA controls biofilm dispersal in Pseudomonas aeruginosa and Rhizobium meliloti.

Journal: BMC research notes 20110101

Title: Evaluation of the sublingual route for administration of influenza H5N1 virosomes in combination with the bacterial second messenger c-di-GMP.

Journal: PloS one 20110101

Title: Modulation of metabolism and switching to biofilm prevail over exopolysaccharide production in the response of Rhizobium alamii to cadmium.

Journal: PloS one 20110101

Title: Complex c-di-GMP signaling networks mediate transition between virulence properties and biofilm formation in Salmonella enterica serovar Typhimurium.

Journal: PloS one 20110101

Title: Characterization of pellicle inhibition in Gluconacetobacter xylinus 53582 by a small molecule, pellicin, identified by a chemical genetics screen.

Journal: PloS one 20110101

Title: Small protein-mediated quorum sensing in a Gram-negative bacterium.

Journal: PloS one 20110101

Title: Phenotypic and genome-wide analysis of an antibiotic-resistant small colony variant (SCV) of Pseudomonas aeruginosa.

Journal: PloS one 20110101

Title: Biochemical and physiological characterization of a BLUF protein-EAL protein complex involved in blue light-dependent degradation of cyclic diguanylate in the purple bacterium Rhodopseudomonas palustris.

Journal: Biochemistry 20101221

Title: Important roles of Tyr43 at the putative heme distal side in the oxygen recognition and stability of the Fe(II)-O2 complex of YddV, a globin-coupled heme-based oxygen sensor diguanylate cyclase.

Journal: Biochemistry 20101214

Title: The EpsE flagellar clutch is bifunctional and synergizes with EPS biosynthesis to promote Bacillus subtilis biofilm formation.

Journal: PLoS genetics 20101201

Title: Cyclic-di-GMP reaches out into the bacterial RNA world.

Journal: Science signaling 20101123

Title: The diguanylate cyclase YddV controls production of the exopolysaccharide poly-N-acetylglucosamine (PNAG) through regulation of the PNAG biosynthetic pgaABCD operon.

Journal: Microbiology (Reading, England) 20101001

Title: Pseudomonas aeruginosa biofilm matrix polysaccharide Psl is regulated transcriptionally by RpoS and post-transcriptionally by RsmA.

Journal: Molecular microbiology 20101001

Title: Genes essential for morphological development and antibiotic production in Streptomyces coelicolor are targets of BldD during vegetative growth.

Journal: Molecular microbiology 20101001

Title: Structural insight into the mechanism of c-di-GMP hydrolysis by EAL domain phosphodiesterases.

Journal: Journal of molecular biology 20100924

Title: Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase.

Journal: Bioorganic & medicinal chemistry 20100915

Title: Role of Vibrio polysaccharide (vps) genes in VPS production, biofilm formation and Vibrio cholerae pathogenesis.

Journal: Microbiology (Reading, England) 20100901

Title: Structural and biochemical determinants of ligand binding by the c-di-GMP riboswitch .

Journal: Biochemistry 20100831

Title: An allosteric self-splicing ribozyme triggered by a bacterial second messenger.

Journal: Science (New York, N.Y.) 20100813

Title: An update on Pseudomonas aeruginosa biofilm formation, tolerance, and dispersal.

Journal: FEMS immunology and medical microbiology 20100801

Title: The yddV-dos operon controls biofilm formation through the regulation of genes encoding curli fibers' subunits in aerobically growing Escherichia coli.

Journal: FEMS immunology and medical microbiology 20100801

Title: 3',5'-Cyclic diguanylic acid: a small nucleotide that makes big impacts.

Journal: Chemical Society reviews 20100801

Title: Genetic analysis of two phosphodiesterases reveals cyclic diguanylate regulation of virulence factors in Dickeya dadantii.

Journal: Molecular microbiology 20100801

Title: Vaccine development in Staphylococcus aureus: taking the biofilm phenotype into consideration.

Journal: FEMS immunology and medical microbiology 20100801

Title: One-flask syntheses of c-di-GMP and the [Rp,Rp] and [Rp,Sp] thiophosphate analogues.

Journal: Organic letters 20100716

Title: Biofilm formation is not required for early-phase transmission of Yersinia pestis.

Journal: Microbiology (Reading, England) 20100701

Title: GGDEF and EAL proteins play different roles in the control of Sinorhizobium meliloti growth, motility, exopolysaccharide production, and competitive nodulation on host alfalfa.

Journal: Acta biochimica et biophysica Sinica 20100615

Title: Asymmetrical distribution of the second messenger c-di-GMP upon bacterial cell division.

Journal: Science (New York, N.Y.) 20100604

Title: A liquid chromatography-coupled tandem mass spectrometry method for quantitation of cyclic di-guanosine monophosphate.

Journal: Journal of microbiological methods 20100601

Title: A post-translational, c-di-GMP-dependent mechanism regulating flagellar motility.

Journal: Molecular microbiology 20100601

Title: Paradigm shift in discovering next-generation anti-infective agents: targeting quorum sensing, c-di-GMP signaling and biofilm formation in bacteria with small molecules.

Journal: Future medicinal chemistry 20100601

Title: Structure of PP4397 reveals the molecular basis for different c-di-GMP binding modes by Pilz domain proteins.

Journal: Journal of molecular biology 20100423

Title: The potential of 3',5'-cyclic diguanylic acid (c-di-GMP) as an effective vaccine adjuvant.

Journal: Vaccine 20100419

Title: The c-di-GMP binding protein YcgR controls flagellar motor direction and speed to affect chemotaxis by a 'backstop brake' mechanism.

Journal: Molecular cell 20100409

Title: Genome-wide screening of genes whose enhanced expression affects glycogen accumulation in Escherichia coli.

Journal: DNA research : an international journal for rapid publication of reports on genes and genomes 20100401

Title: Genomic structure of an economically important cyanobacterium, Arthrospira (Spirulina) platensis NIES-39.

Journal: DNA research : an international journal for rapid publication of reports on genes and genomes 20100401

Title: Identification and molecular characterization of a cyclic-di-GMP effector protein, PlzA (BB0733): additional evidence for the existence of a functional cyclic-di-GMP regulatory network in the Lyme disease spirochete, Borrelia burgdorferi.

Journal: FEMS immunology and medical microbiology 20100301

Title: YfiBNR mediates cyclic di-GMP dependent small colony variant formation and persistence in Pseudomonas aeruginosa.

Journal: PLoS pathogens 20100301

Title: The effect of c-di-GMP (3'-5'-cyclic diguanylic acid) on the biofilm formation and adherence of Streptococcus mutans.

Journal: Microbiological research 20100227

Title: The cAMP receptor-like protein CLP is a novel c-di-GMP receptor linking cell-cell signaling to virulence gene expression in Xanthomonas campestris.

Journal: Journal of molecular biology 20100226

Title: Vibrio cholerae VpsT regulates matrix production and motility by directly sensing cyclic di-GMP.

Journal: Science (New York, N.Y.) 20100212

Title: Characterization of starvation-induced dispersion in Pseudomonas putida biofilms: genetic elements and molecular mechanisms.

Journal: Molecular microbiology 20100201

Title: Beyond antibiotic resistance: integrating conjugative elements of the SXT/R391 family that encode novel diguanylate cyclases participate to c-di-GMP signalling in Vibrio cholerae.

Journal: Environmental microbiology 20100201

Title: Complex regulatory network encompassing the Csr, c-di-GMP and motility systems of Salmonella Typhimurium.

Journal: Environmental microbiology 20100201

Title: Pseudomonas aeruginosa uses a cyclic-di-GMP-regulated adhesin to reinforce the biofilm extracellular matrix.

Journal: Molecular microbiology 20100201

Title: Structure, function, and evolution of the Thiomonas spp. genome.

Journal: PLoS genetics 20100201

Title: Cyclic di-GMP signalling controls virulence properties of Salmonella enterica serovar Typhimurium at the mucosal lining.

Journal: Environmental microbiology 20100101

Title: Monitoring of diguanylate cyclase activity and of cyclic-di-GMP biosynthesis by whole-cell assays suitable for high-throughput screening of biofilm inhibitors.

Journal: Applied microbiology and biotechnology 20100101

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Journal: Genes & development 20080901

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Tags:61093-23-0 Molecular Formula|61093-23-0 MDL|61093-23-0 SMILES|61093-23-0 bis(3',5')-cyclic diguanylic acid
Catalog No.: AA00EPM1
61093-23-0,MFCD31563661
61093-23-0 | bis(3',5')-cyclic diguanylic acid
Pack Size: 1mg
Purity: ≥98%
2 weeks
$1,414.00 $990.00
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Technical Information
Catalog Number: AA00EPM1
Chemical Name: bis(3',5')-cyclic diguanylic acid
CAS Number: 61093-23-0
Molecular Formula: C20H24N10O14P2
Molecular Weight: 690.4107
MDL Number: MFCD31563661
SMILES: O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]3O[C@H]([C@@H]([C@@H]3OP(=O)(OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O)O)O)n1cnc2c1nc(N)[nH]c2=O
Properties
Complexity: 1340  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 8  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 46  
Hydrogen Bond Acceptor Count: 18  
Hydrogen Bond Donor Count: 8  
Isotope Atom Count: 0  
Rotatable Bond Count: 2  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -6.8  
Literature fold

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Title: Structure of STING bound to cyclic di-GMP reveals the mechanism of cyclic dinucleotide recognition by the immune system.

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Title: Crystal structures of STING protein reveal basis for recognition of cyclic di-GMP.

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Title: Engineered allosteric ribozymes that sense the bacterial second messenger cyclic diguanosyl 5'-monophosphate.

Journal: Analytical chemistry20120605

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Journal: Microbiology (Reading, England)20120601

Title: Vaccination of mice with recombinant bacille Calmette-Guérin harboring Rv1357c protects similarly to native BCG.

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Title: The YfiBNR signal transduction mechanism reveals novel targets for the evolution of persistent Pseudomonas aeruginosa in cystic fibrosis airways.

Journal: PLoS pathogens20120601

Title: Nitric oxide modulates bacterial biofilm formation through a multicomponent cyclic-di-GMP signaling network.

Journal: Molecular cell20120525

Title: Allosteric tertiary interactions preorganize the c-di-GMP riboswitch and accelerate ligand binding.

Journal: ACS chemical biology20120518

Title: [Exogenous 3', 5'-cyclic diguanylic acid prevents caries formation in rats].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University20120501

Title: Cellular levels and binding of c-di-GMP control subcellular localization and activity of the Vibrio cholerae transcriptional regulator VpsT.

Journal: PLoS pathogens20120501

Title: You've come a long way: c-di-GMP signaling.

Journal: Current opinion in microbiology20120401

Title: The orphan histidine protein kinase SgmT is a c-di-GMP receptor and regulates composition of the extracellular matrix together with the orphan DNA binding response regulator DigR in Myxococcus xanthus.

Journal: Molecular microbiology20120401

Title: Nitric oxide regulation of cyclic di-GMP synthesis and hydrolysis in Shewanella woodyi.

Journal: Biochemistry20120313

Title: Differential binding of 2'-biotinylated analogs of c-di-GMP with c-di-GMP riboswitches and binding proteins.

Journal: Molecular bioSystems20120301

Title: A C-di-GMP-proflavine-hemin supramolecular complex has peroxidase activity--implication for a simple colorimetric detection.

Journal: Molecular bioSystems20120301

Title: One-flask synthesis of cyclic diguanosine monophosphate (c-di-GMP).

Journal: Current protocols in nucleic acid chemistry20120301

Title: Crystallization and preliminary X-ray diffraction characterization of the XccFimX(EAL)-c-di-GMP and XccFimX(EAL)-c-di-GMP-XccPilZ complexes from Xanthomonas campestris.

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Journal: Yao xue xue bao = Acta pharmaceutica Sinica20120301

Title: The extremophile Acidithiobacillus ferrooxidans possesses a c-di-GMP signalling pathway that could play a significant role during bioleaching of minerals.

Journal: Letters in applied microbiology20120201

Title: A chemical proteomics approach to identify c-di-GMP binding proteins in Pseudomonas aeruginosa.

Journal: Journal of microbiological methods20120201

Title: Discrete cyclic di-GMP-dependent control of bacterial predation versus axenic growth in Bdellovibrio bacteriovorus.

Journal: PLoS pathogens20120201

Title: Why do microorganisms produce rhamnolipids?

Journal: World journal of microbiology & biotechnology20120201

Title: Dynamic energy landscapes of riboswitches help interpret conformational rearrangements and function.

Journal: PLoS computational biology20120201

Title: Oligomer formation of the bacterial second messenger c-di-GMP: reaction rates and equilibrium constants indicate a monomeric state at physiological concentrations.

Journal: Journal of the American Chemical Society20120118

Title: Diamidinium and iminium aromatics as new aggregators of the bacterial signaling molecule, c-di-GMP.

Journal: Bioorganic & medicinal chemistry letters20120115

Title: Structural and biochemical characterization of linear dinucleotide analogues bound to the c-di-GMP-I aptamer.

Journal: Biochemistry20120110

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Journal: Nature communications20120103

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Title: A previously uncharacterized gene stm0551 plays a repressive role in the regulation of type 1 fimbriae in Salmonella enterica serotype Typhimurium.

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Title: Comparative analysis of diguanylate cyclase and phosphodiesterase genes in Klebsiella pneumoniae.

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Title: Enzymatically active and inactive phosphodiesterases and diguanylate cyclases are involved in regulation of Motility or sessility in Escherichia coli CFT073.

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Title: N-Acetylglucosamine-dependent biofilm formation in Pectobacterium atrosepticum is cryptic and activated by elevated c-di-GMP levels.

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Title: The Pseudomonas aeruginosa sensor RetS switches type III and type VI secretion via c-di-GMP signalling.

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Title: Overlapping and unique contributions of two conserved polysaccharide loci in governing distinct survival phenotypes in Vibrio vulnificus.

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Journal: RNA (New York, N.Y.)20111101

Title: A multi-repeat adhesin of the phytopathogen, Pectobacterium atrosepticum, is secreted by a Type I pathway and is subject to complex regulation involving a non-canonical diguanylate cyclase.

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Title: Extracellular nucleases and extracellular DNA play important roles in Vibrio cholerae biofilm formation.

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Title: The CRP/FNR family protein Bcam1349 is a c-di-GMP effector that regulates biofilm formation in the respiratory pathogen Burkholderia cenocepacia.

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Title: Fitness landscape of antibiotic tolerance in Pseudomonas aeruginosa biofilms.

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Title: The atypical two-component sensor kinase Lpl0330 from Legionella pneumophila controls the bifunctional diguanylate cyclase-phosphodiesterase Lpl0329 to modulate bis-(3'-5')-cyclic dimeric GMP synthesis.

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Title: c-di-GMP protects against intranasal Acinetobacter baumannii infection in mice by chemokine induction and enhanced neutrophil recruitment.

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Title: Modulation of Pseudomonas aeruginosa surface-associated group behaviors by individual amino acids through c-di-GMP signaling.

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Title: c-di-AMP is a new second messenger in Staphylococcus aureus with a role in controlling cell size and envelope stress.

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Title: Regulatory cohesion of cell cycle and cell differentiation through interlinked phosphorylation and second messenger networks.

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Title: The bacterial second messenger c-di-GMP: mechanisms of signalling.

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Title: MrkH, a novel c-di-GMP-dependent transcriptional activator, controls Klebsiella pneumoniae biofilm formation by regulating type 3 fimbriae expression.

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Title: Intranasal c-di-GMP-adjuvanted plant-derived H5 influenza vaccine induces multifunctional Th1 CD4+ cells and strong mucosal and systemic antibody responses in mice.

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Title: The diguanylate cyclase, Rrp1, regulates critical steps in the enzootic cycle of the Lyme disease spirochetes.

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Title: Cyclic diguanylate turnover mediated by the sole GGDEF/EAL response regulator in Pseudomonas putida: its role in the rhizosphere and an analysis of its target processes.

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Title: Borrelia burgdorferi requires glycerol for maximum fitness during the tick phase of the enzootic cycle.

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Title: Conservative change to the phosphate moiety of cyclic diguanylic monophosphate remarkably affects its polymorphism and ability to bind DGC, PDE, and PilZ proteins.

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Title: Cyclic di-GMP is essential for the survival of the lyme disease spirochete in ticks.

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Title: Quorum sensing and c-di-GMP-dependent alterations in gene transcripts and virulence-associated phenotypes in a clinical isolate of Aeromonas hydrophila.

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Title: c-di-GMP can form remarkably stable G-quadruplexes at physiological conditions in the presence of some planar intercalators.

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Title: Cyclic di-GMP activation of polynucleotide phosphorylase signal-dependent RNA processing.

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Title: Thiazole orange-induced c-di-GMP quadruplex formation facilitates a simple fluorescent detection of this ubiquitous biofilm regulating molecule.

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Title: GGDEF proteins YeaI, YedQ, and YfiN reduce early biofilm formation and swimming motility in Escherichia coli.

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Title: Engineering a novel c-di-GMP-binding protein for biofilm dispersal.

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Title: c-di-GMP turn-over in Clostridium difficile is controlled by a plethora of diguanylate cyclases and phosphodiesterases.

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Title: Structural characterization reveals that a PilZ domain protein undergoes substantial conformational change upon binding to cyclic dimeric guanosine monophosphate.

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Title: A c-di-GMP effector system controls cell adhesion by inside-out signaling and surface protein cleavage.

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Title: Interaction of the diguanylate cyclase YdeH of Escherichia coli with 2',(3')-substituted purine and pyrimidine nucleotides.

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Title: Surface sensing in Vibrio parahaemolyticus triggers a programme of gene expression that promotes colonization and virulence.

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Title: Systematic analysis of cyclic di-GMP signalling enzymes and their role in biofilm formation and virulence in Yersinia pestis.

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Title: Biosynthesis of the Pseudomonas aeruginosa Extracellular Polysaccharides, Alginate, Pel, and Psl.

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Title: Complex c-di-GMP signaling networks mediate transition between virulence properties and biofilm formation in Salmonella enterica serovar Typhimurium.

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Title: Biochemical and physiological characterization of a BLUF protein-EAL protein complex involved in blue light-dependent degradation of cyclic diguanylate in the purple bacterium Rhodopseudomonas palustris.

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Title: The diguanylate cyclase YddV controls production of the exopolysaccharide poly-N-acetylglucosamine (PNAG) through regulation of the PNAG biosynthetic pgaABCD operon.

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Title: Pseudomonas aeruginosa biofilm matrix polysaccharide Psl is regulated transcriptionally by RpoS and post-transcriptionally by RsmA.

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Title: Genes essential for morphological development and antibiotic production in Streptomyces coelicolor are targets of BldD during vegetative growth.

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Title: GGDEF and EAL proteins play different roles in the control of Sinorhizobium meliloti growth, motility, exopolysaccharide production, and competitive nodulation on host alfalfa.

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Title: The effect of c-di-GMP (3'-5'-cyclic diguanylic acid) on the biofilm formation and adherence of Streptococcus mutans.

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Title: Characterization of starvation-induced dispersion in Pseudomonas putida biofilms: genetic elements and molecular mechanisms.

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Title: Beyond antibiotic resistance: integrating conjugative elements of the SXT/R391 family that encode novel diguanylate cyclases participate to c-di-GMP signalling in Vibrio cholerae.

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Title: Complex regulatory network encompassing the Csr, c-di-GMP and motility systems of Salmonella Typhimurium.

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Title: Cyclic di-GMP signalling controls virulence properties of Salmonella enterica serovar Typhimurium at the mucosal lining.

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Title: Monitoring of diguanylate cyclase activity and of cyclic-di-GMP biosynthesis by whole-cell assays suitable for high-throughput screening of biofilm inhibitors.

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Title: YybT is a signaling protein that contains a cyclic dinucleotide phosphodiesterase domain and a GGDEF domain with ATPase activity.

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Title: Cyclic-di-GMP-mediated signalling within the sigma network of Escherichia coli.

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Title: Allosteric control of cyclic di-GMP signaling.

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Title: The EAL domain protein VieA is a cyclic diguanylate phosphodiesterase.

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Title: Cyclic diguanylate (c-di-GMP) regulates Vibrio cholerae biofilm formation.

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Title: Identification of genes involved in the switch between the smooth and rugose phenotypes of Vibrio cholerae.

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