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72909-34-3,MFCD00043125
Catalog No.:AA003KFQ

72909-34-3 | 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

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100mg
97%
in stock  
$8.00   $6.00
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250mg
97%
in stock  
$18.00   $13.00
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1g
98%
in stock  
$54.00   $38.00
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5g
98%
in stock  
$170.00   $119.00
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25g
98%
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$643.00   $450.00
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100g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003KFQ
Chemical Name:
4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
CAS Number:
72909-34-3
Molecular Formula:
C14H6N2O8
Molecular Weight:
330.2060
MDL Number:
MFCD00043125
SMILES:
OC(=O)c1cc(nc2c1c1[nH]c(cc1C(=O)C2=O)C(=O)O)C(=O)O
Properties
Properties
 
BP:
1018.6°C at 760 mmHg  
Form:
Solid  
MP:
222 - 224°C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
647  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
XLogP3:
-0.1  

Downstream Synthesis Route

[1]JournaloftheChemicalSociety.Chemicalcommunications,1990,p.1608-1611

[2]JournaloftheChemicalSociety.PerkintransactionsII,1992,p.1245-1251

[1]JournaloftheChemicalSociety.PerkintransactionsII,1992,p.1245-1251

[2]JournaloftheChemicalSociety.Chemicalcommunications,1990,p.1608-1611

[1]JournaloftheChemicalSociety.PerkintransactionsII,1992,p.1245-1251

[1]JournaloftheChemicalSociety.PerkintransactionsII,1992,p.1245-1251

[1]JournaloftheChemicalSociety.PerkintransactionsII,1992,p.1245-1251

Literature

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Journal: Toxicology in vitro : an international journal published in association with BIBRA 20171201

Title: The role of oxidative stress in DNA damage in pancreatic β cells induced by di-(2-ethylhexyl) phthalate.

Journal: Chemico-biological interactions 20170301

Title: Neuroprotective effects of pyrroloquinoline quinone against rotenone injury in primary cultured midbrain neurons and in a rat model of Parkinson's disease.

Journal: Neuropharmacology 20160901

Title: Pyrroloquinoline quinone-conferred neuroprotection in rotenone models of Parkinson's disease.

Journal: Toxicology letters 20151104

Title: Pyrroloquinoline quinone (PQQ) has potential to ameliorate streptozotocin-induced diabetes mellitus and oxidative stress in mice: A histopathological and biochemical study.

Journal: Chemico-biological interactions 20151005

Title: Pyrroloquinoline quinone (PQQ) producing Escherichia coli Nissle 1917 (EcN) alleviates age associated oxidative stress and hyperlipidemia, and improves mitochondrial function in ageing rats.

Journal: Experimental gerontology 20150601

Title: Involvement of ERK1/2 pathway in neuroprotective effects of pyrroloquinoline quinine against rotenone-induced SH-SY5Y cell injury.

Journal: Neuroscience 20140613

Title: Coupling of pyrroloquinoline quinone dependent glucose dehydrogenase to (cytochrome c/DNA)-multilayer systems on electrodes.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20121201

Title: Electrochemical switching of photoelectrochemical processes at CdS QDs and photosystem I-modified electrodes.

Journal: ACS nano 20121023

Title: Pyrroloquinoline quinone stimulates epithelial cell proliferation by activating epidermal growth factor receptor through redox cycling.

Journal: Free radical biology & medicine 20120915

Title: High-temperature sorbose fermentation with thermotolerant Gluconobacter frateurii CHM43 and its mutant strain adapted to higher temperature.

Journal: Applied microbiology and biotechnology 20120901

Title: Pyrroloquinoline quinone rescues hippocampal neurons from glutamate-induced cell death through activation of Nrf2 and up-regulation of antioxidant genes.

Journal: Genetics and molecular research : GMR 20120816

Title: Cofactor biosynthesis through protein post-translational modification.

Journal: Current opinion in chemical biology 20120401

Title: The neuroprotective effect of pyrroloquinoline quinone on traumatic brain injury.

Journal: Journal of neurotrauma 20120320

Title: Distribution and properties of the genes encoding the biosynthesis of the bacterial cofactor, pyrroloquinoline quinone.

Journal: Biochemistry 20120320

Title: Pyrroloquinoline quinone modulates the kinetic parameters of the mammalian selenoprotein thioredoxin reductase 1 and is an inhibitor of glutathione reductase.

Journal: Biochemical pharmacology 20120315

Title: The active (ADHa) and inactive (ADHi) forms of the PQQ-alcohol dehydrogenase from Gluconacetobacter diazotrophicus differ in their respective oligomeric structures and redox state of their corresponding prosthetic groups.

Journal: FEMS microbiology letters 20120301

Title: Characterization of different FAD-dependent glucose dehydrogenases for possible use in glucose-based biosensors and biofuel cells.

Journal: Analytical and bioanalytical chemistry 20120201

Title: [Study of chemical kinetics between pyrroloquinoline quinine and D-serine in body by ion-pair liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20120201

Title: The complete genome sequence of Pantoea ananatis AJ13355, an organism with great biotechnological potential.

Journal: Applied microbiology and biotechnology 20120101

Title: Exploiting adaptive laboratory evolution of Streptomyces clavuligerus for antibiotic discovery and overproduction.

Journal: PloS one 20120101

Title: Practical application of methanol-mediated mutualistic symbiosis between Methylobacterium species and a roof greening moss, Racomitrium japonicum.

Journal: PloS one 20120101

Title: Jacaranone induces apoptosis in melanoma cells via ROS-mediated downregulation of Akt and p38 MAPK activation and displays antitumor activity in vivo.

Journal: PloS one 20120101

Title: Influence of adding pyrroloquinoline quinone to parenteral nutrition on gut-associated lymphoid tissue.

Journal: JPEN. Journal of parenteral and enteral nutrition 20110901

Title: [Effects of pyrroloquinoline quinone on proliferation and expression of c-fos, c-jun, CREB and PCNA in cultured Schwann cells].

Journal: Zhonghua zheng xing wai ke za zhi = Zhonghua zhengxing waike zazhi = Chinese journal of plastic surgery 20110701

Title: Identification of Pantoea ananatis gene encoding membrane pyrroloquinoline quinone (PQQ)-dependent glucose dehydrogenase and pqqABCDEF operon essential for PQQ biosynthesis.

Journal: FEMS microbiology letters 20110501

Title: Absorbance-based assay for membrane disruption by antimicrobial peptides and synthetic copolymers using pyrroloquinoline quinone-loaded liposomes.

Journal: Analytical biochemistry 20110415

Title: The neuroprotective action of pyrroloquinoline quinone against glutamate-induced apoptosis in hippocampal neurons is mediated through the activation of PI3K/Akt pathway.

Journal: Toxicology and applied pharmacology 20110401

Title: Purification, crystallization and preliminary X-ray crystallographic analysis of a methanol dehydrogenase from the marine bacterium Methylophaga aminisulfidivorans MP(T).

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20110401

Title: The enzymatic reaction-induced configuration change of the prosthetic group PQQ of methanol dehydrogenase.

Journal: Biochemical and biophysical research communications 20110325

Title: Kinetic study of the quenching reaction of singlet oxygen by Pyrroloquinolinequinol (PQQH(2), a reduced form of Pyrroloquinolinequinone) in micellar solution.

Journal: Journal of agricultural and food chemistry 20110309

Title: Characterization of a protein-generated O₂ binding pocket in PqqC, a cofactorless oxidase catalyzing the final step in PQQ production.

Journal: Biochemistry 20110308

Title: Characterization and engineering of a novel pyrroloquinoline quinone dependent glucose dehydrogenase from Sorangium cellulosum So ce56.

Journal: Molecular biotechnology 20110301

Title: Uranium exerts acute toxicity by binding to pyrroloquinoline quinone cofactor.

Journal: Environmental science & technology 20110201

Title: Bioinformatic evidence for a widely distributed, ribosomally produced electron carrier precursor, its maturation proteins, and its nicotinoprotein redox partners.

Journal: BMC genomics 20110101

Title: Acute reduction of serum 8-iso-PGF2-alpha and advanced oxidation protein products in vivo by a polyphenol-rich beverage; a pilot clinical study with phytochemical and in vitro antioxidant characterization.

Journal: Nutrition journal 20110101

Title: An Extracellular Tetrathionate Hydrolase from the Thermoacidophilic Archaeon Acidianus Ambivalens with an Activity Optimum at pH 1.

Journal: Frontiers in microbiology 20110101

Title: Altering pyrroloquinoline quinone nutritional status modulates mitochondrial, lipid, and energy metabolism in rats.

Journal: PloS one 20110101

Title: Genome organization of epidemic Acinetobacter baumannii strains.

Journal: BMC microbiology 20110101

Title: Peritoneal dialysis in diabetics: there is room for more.

Journal: International journal of nephrology 20110101

Title: Production and radioprotective effects of pyrroloquinoline quinone.

Journal: International journal of molecular sciences 20110101

Title: Application of oxygen-independent biosensor for testing yeast fermentation capacity.

Journal: Biosensors & bioelectronics 20101015

Title: Catalytic properties and crystal structure of quinoprotein aldose sugar dehydrogenase from hyperthermophilic archaeon Pyrobaculum aerophilum.

Journal: Archives of biochemistry and biophysics 20101015

Title: Development of a (PQQ)-GDH-anode based on MWCNT-modified gold and its application in a glucose/O2-biofuel cell.

Journal: Biosensors & bioelectronics 20101015

Title: Interaction of PqqE and PqqD in the pyrroloquinoline quinone (PQQ) biosynthetic pathway links PqqD to the radical SAM superfamily.

Journal: Chemical communications (Cambridge, England) 20101007

Title: Survival of phosphate-solubilizing bacteria against DNA damaging agents.

Journal: Canadian journal of microbiology 20101001

Title: [Knockout and function analysis of pqqL gene in Escherichia coli].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20101001

Title: The quinohaemoprotein alcohol dehydrogenase from Gluconacetobacter xylinus: molecular and catalytic properties.

Journal: Archives of microbiology 20100901

Title: Structural studies of mutant forms of the PQQ-forming enzyme PqqC in the presence of product and substrate.

Journal: Proteins 20100815

Title: Identification of transcriptional networks responding to pyrroloquinoline quinone dietary supplementation and their influence on thioredoxin expression, and the JAK/STAT and MAPK pathways.

Journal: The Biochemical journal 20100801

Title: Recombinant tetrathionate hydrolase from Acidithiobacillus ferrooxidans requires exposure to acidic conditions for proper folding.

Journal: FEMS microbiology letters 20100801

Title: Pyrroloquinoline quinone-dependent carbohydrate dehydrogenase: activity enhancement and the role of artificial electron acceptors.

Journal: Biotechnology journal 20100801

Title: [Isolation PQQ biosynthesis gene cluster from Gluconobacter oxydans based on sorbose-dehydrogenase activity].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20100801

Title: Visual detection of single-stranded target DNA using pyrroloquinoline-quinone-loaded liposomes as a tracer.

Journal: Analytical biochemistry 20100615

Title: Pyrroloquinoline quinone biosynthesis in Escherichia coli through expression of the Gluconobacter oxydans pqqABCDE gene cluster.

Journal: Journal of industrial microbiology & biotechnology 20100601

Title: Alcohol dehydrogenase of acetic acid bacteria: structure, mode of action, and applications in biotechnology.

Journal: Applied microbiology and biotechnology 20100501

Title: PQQ-dependent alcohol dehydrogenase (QEDH) of Pseudomonas aeruginosa is involved in catabolism of acyclic terpenes.

Journal: Journal of basic microbiology 20100401

Title: Cofactor-independent oxidases and oxygenases.

Journal: Applied microbiology and biotechnology 20100401

Title: The membrane-bound quinohemoprotein alcohol dehydrogenase from Gluconacetobacter diazotrophicus PAL5 carries a [2Fe-2S] cluster.

Journal: Biochemistry 20100323

Title: Micro-biofuel cell powered by glucose/O2 based on electro-deposition of enzyme, conducting polymer and redox mediators: preparation, characterization and performance in human serum.

Journal: Biosensors & bioelectronics 20100215

Title: Feasibility study of introducing redox property by modification of PMBN polymer for biofuel cell applications.

Journal: Applied biochemistry and biotechnology 20100201

Title: Pyrroloquinoline quinone stimulates mitochondrial biogenesis through cAMP response element-binding protein phosphorylation and increased PGC-1alpha expression.

Journal: The Journal of biological chemistry 20100101

Title: The PQQ biosynthetic operons and their transcriptional regulation in Pseudomonas aeruginosa.

Journal: Archives of microbiology 20100101

Title: Pyrroloquinoline quinone inhibits the fibrillation of amyloid proteins.

Journal: Prion 20100101

Title: Pro-oxidant action of pyrroloquinoline quinone: characterization of protein oxidative modifications.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Highly conserved Asp-204 and Gly-776 are important for activity of the quinoprotein glucose dehydrogenase of Escherichia coli and for mineral phosphate solubilization.

Journal: Journal of molecular microbiology and biotechnology 20100101

Title: [The roles of PI3K/Akt pathway in proliferation of Schwann cells promoted by pyrroloquinoline quinone].

Journal: Zhonghua zheng xing wai ke za zhi = Zhonghua zhengxing waike zazhi = Chinese journal of plastic surgery 20100101

Title: The inhibitory effect of pyrroloquinoline quinone on the amyloid formation and cytotoxicity of truncated alpha-synuclein.

Journal: Molecular neurodegeneration 20100101

Title: The neurogenic basic helix-loop-helix transcription factor NeuroD6 confers tolerance to oxidative stress by triggering an antioxidant response and sustaining the mitochondrial biomass.

Journal: ASN neuro 20100101

Title: Role of glutathione in augmenting the anticancer activity of pyrroloquinoline quinone (PQQ).

Journal: Redox report : communications in free radical research 20100101

Title: Gene expression in Pseudomonas aeruginosa swarming motility.

Journal: BMC genomics 20100101

Title: Mechanistic and functional versatility of radical SAM enzymes.

Journal: F1000 biology reports 20100101

Title: Emission quench of water-soluble ZnS-AgInS2 solid solution nanocrystals and its application to chemosensors.

Journal: Chemical communications (Cambridge, England) 20091228

Title: Characterization of the mineral phosphate solubilizing activity of Serratia marcescens CTM 50650 isolated from the phosphate mine of Gafsa.

Journal: Archives of microbiology 20091101

Title: Protective effect of pyrroloquinoline quinone against Abeta-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.

Journal: Neuroscience letters 20091030

Title: Pyrroloquinoline quinone biogenesis: demonstration that PqqE from Klebsiella pneumoniae is a radical S-adenosyl-L-methionine enzyme.

Journal: Biochemistry 20091027

Title: Xanthomonas campestris PqqD in the pyrroloquinoline quinone biosynthesis operon adopts a novel saddle-like fold that possibly serves as a PQQ carrier.

Journal: Proteins 20090901

Title: Potential physiological importance of pyrroloquinoline quinone.

Journal: Alternative medicine review : a journal of clinical therapeutic 20090901

Title: Strategy for the isolation of native dehydrogenases with potential for biosensor development from the organism Hyphomicrobium zavarzinii ZV580.

Journal: Journal of chromatography. A 20090417

Title: Quinoprotein ethanol dehydrogenase from Pseudomonas aeruginosa: the unusual disulfide ring formed by adjacent cysteine residues is essential for efficient electron transfer to cytochrome c550.

Journal: Archives of microbiology 20090401

Title: Protection of pyrroloquinoline quinone against methylmercury-induced neurotoxicity via reducing oxidative stress.

Journal: Free radical research 20090301

Title: Application of a thiol-specific electrocatalytic electrode for real-time amperometric monitoring of enzymatic hydrolysis.

Journal: The Analyst 20090301

Title: Pyrroloquinoline quinone-doped polymeric nanospheres as sensitive tracer for binding assays.

Journal: Analytical chemistry 20090215

Title: Effect of pyrroloquinoline quinone (PQQ) on melanogenic protein expression in murine B16 melanoma.

Journal: Journal of dermatological science 20090201

Title: Quantification of the expression of reference and alcohol dehydrogenase genes of some acetic acid bacteria in different growth conditions.

Journal: Journal of applied microbiology 20090201

Title: Kinetic study of the antioxidant activity of pyrroloquinolinequinol (PQQH(2), a reduced form of pyrroloquinolinequinone) in micellar solution.

Journal: Journal of agricultural and food chemistry 20090128

Title: Pyrroloquinoline quinone attenuates iNOS gene expression in the injured spinal cord.

Journal: Biochemical and biophysical research communications 20090109

Title: Heterogeneous electron-transfer kinetics for PQQ covalently attached to aminoalkanethiol monolayers on gold.

Journal: Colloids and surfaces. B, Biointerfaces 20090101

Title: Glucose oxidation and PQQ-dependent dehydrogenases in Gluconobacter oxydans.

Journal: Journal of molecular microbiology and biotechnology 20090101

Title: Methylobacterium genome sequences: a reference blueprint to investigate microbial metabolism of C1 compounds from natural and industrial sources.

Journal: PloS one 20090101

Title: Analytical interferences in point-of-care testing glucometers by icodextrin and its metabolites: an overview.

Journal: Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis 20090101

Title: Evolutionary constraints permeate large metabolic networks.

Journal: BMC evolutionary biology 20090101

Title: Effect of vitamin E on learning and memory deficit in aged rats.

Journal: Journal of nutritional science and vitaminology 20090101

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Title: In vitro protective effects of pyrroloquinoline quinone on methylmercury-induced neurotoxicity.

Journal: Environmental toxicology and pharmacology 20090101

Title: Recent advances in nanotechnology applied to biosensors.

Journal: Sensors (Basel, Switzerland) 20090101

Title: Magnetic particle-based hybrid platforms for bioanalytical sensors.

Journal: Sensors (Basel, Switzerland) 20090101

Title: Isolation and purification of PQQ-dependent lactate dehydrogenase from Gluconobacter and use for direct electron transfer at carbon and gold electrodes.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20081101

Title: Menaquinone as well as ubiquinone as a bound quinone crucial for catalytic activity and intramolecular electron transfer in Escherichia coli membrane-bound glucose dehydrogenase.

Journal: The Journal of biological chemistry 20081017

Title: A tightly bound quinone functions in the ubiquinone reaction sites of quinoprotein alcohol dehydrogenase of an acetic acid bacterium, Gluconobacter suboxydans.

Journal: Bioscience, biotechnology, and biochemistry 20081001

Title: A pyrroloquinoline quinine-dependent membrane-bound d-sorbitol dehydrogenase from Gluconobacter oxydans exhibits an ordered Bi Bi reaction mechanism.

Journal: Archives of biochemistry and biophysics 20080915

Title: Amino acid residues interacting with both the bound quinone and coenzyme, pyrroloquinoline quinone, in Escherichia coli membrane-bound glucose dehydrogenase.

Journal: The Journal of biological chemistry 20080808

Title: SECM visualization of the spatial variability of enzyme-polymer spots. 3. Enzymatic feedback mode.

Journal: Analytical and bioanalytical chemistry 20080701

Title: Pyrroloquinoline quinone prevents oxidative stress-induced neuronal death probably through changes in oxidative status of DJ-1.

Journal: Biological & pharmaceutical bulletin 20080701

Title: The PQQ-alcohol dehydrogenase of Gluconacetobacter diazotrophicus.

Journal: International journal of food microbiology 20080630

Title: Direct detection of formaldehyde in air by a novel NAD+- and glutathione-independent formaldehyde dehydrogenase-based biosensor.

Journal: Talanta 20080515

Title: Inactivation of pqq genes of Enterobacter intermedium 60-2G reduces antifungal activity and induction of systemic resistance.

Journal: FEMS microbiology letters 20080501

Title: Distinct physiological roles of two membrane-bound dehydrogenases responsible for D-sorbitol oxidation in Gluconobacter frateurii.

Journal: Bioscience, biotechnology, and biochemistry 20080301

Title: Pyrroloquinoline quinone is a plant growth promotion factor produced by Pseudomonas fluorescens B16.

Journal: Plant physiology 20080201

Title: Genetic analyses and molecular characterization of the pathways involved in the conversion of 2-phenylethylamine and 2-phenylethanol into phenylacetic acid in Pseudomonas putida U.

Journal: Environmental microbiology 20080201

Title: In vitro studies indicate a quinone is involved in bacterial Mn(II) oxidation.

Journal: Archives of microbiology 20080101

Title: Simultaneous determination of blood glucose and isoleucine levels in rats after chronic alcohol exposure by microwave-assisted derivatization and isotope dilution gas chromatography/mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20080101

Title: Pyrroloquinoline Quinone (PQQ) Prevents Cognitive Deficit Caused by Oxidative Stress in Rats.

Journal: Journal of clinical biochemistry and nutrition 20080101

Title: The pyrroloquinoline quinone biosynthesis pathway revisited: a structural approach.

Journal: BMC biochemistry 20080101

Title: Complete genome sequence of the extremely acidophilic methanotroph isolate V4, Methylacidiphilum infernorum, a representative of the bacterial phylum Verrucomicrobia.

Journal: Biology direct 20080101

Title: Genomic diversity within the Enterobacter cloacae complex.

Journal: PloS one 20080101

Title: Function of a bound ubiquinone in Escherichia coli quinoprotein glucose dehydrogenase.

Journal: BioFactors (Oxford, England) 20080101

Title: [Establishment of the screening method and isolation of PQQ producing strains].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20071201

Title: Pyrroloquinoline quinone preserves mitochondrial function and prevents oxidative injury in adult rat cardiac myocytes.

Journal: Biochemical and biophysical research communications 20071116

Title: Simple and sensitive method for pyrroloquinoline quinone (PQQ) analysis in various foods using liquid chromatography/electrospray-ionization tandem mass spectrometry.

Journal: Journal of agricultural and food chemistry 20070905

Title: Novel aspects of symbiotic (polyvinyl alcohol) biodegradation.

Journal: Applied microbiology and biotechnology 20070901

Title: The highly tolerant acetic acid bacterium Gluconacetobacter europaeus adapts to the presence of acetic acid by changes in lipid composition, morphological properties and PQQ-dependent ADH expression.

Journal: Extremophiles : life under extreme conditions 20070701

Title: Pyrroloquinoline quinone biogenesis: characterization of PqqC and its H84N and H84A active site variants.

Journal: Biochemistry 20070619

Title: Improved specificity of reagentless amperometric PQQ-sGDH glucose biosensors by using indirectly heated electrodes.

Journal: Biosensors & bioelectronics 20070615

Title: Activation of Ras signaling pathways by pyrroloquinoline quinone in NIH3T3 mouse fibroblasts.

Journal: International journal of molecular medicine 20070501

Title: Factors required for the catalytic reaction of PqqC/D which produces pyrroloquinoline quinone.

Journal: Biochemical and biophysical research communications 20070302

Title: Pyrroloquinoline quinone is a potent neuroprotective nutrient against 6-hydroxydopamine-induced neurotoxicity.

Journal: Neurochemical research 20070301

Title: Microstructural and tensile properties of elastin-based polypeptides crosslinked with genipin and pyrroloquinoline quinone.

Journal: Biopolymers 20070215

Title: The preferred reaction path for the oxidation of methanol by PQQ-containing methanol dehydrogenase: addition-elimination versus hydride-transfer mechanism.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: In silico panning for a non-competitive peptide inhibitor.

Journal: BMC bioinformatics 20070101

Title: Comparative genomics of bacterial and plant folate synthesis and salvage: predictions and validations.

Journal: BMC genomics 20070101

Title: Chromium hexacyanoferrate modified biosensor based on PQQ-dependent glucose dehydrogenase.

Journal: Conference proceedings : ... Annual International Conference of the IEEE Engineering in Medicine and Biology Society. IEEE Engineering in Medicine and Biology Society. Annual Conference 20070101

Title: Complex and charge transfer between TiO2 and pyrroloquinoline quinone.

Journal: The journal of physical chemistry. B 20061221

Title: Pyrroloquinoline quinone nutritional status alters lysine metabolism and modulates mitochondrial DNA content in the mouse and rat.

Journal: Biochimica et biophysica acta 20061101

Title: Pyrroloquinoline quinone (PQQ) prevents fibril formation of alpha-synuclein.

Journal: Biochemical and biophysical research communications 20061027

Title: Soluble aldose sugar dehydrogenase from Escherichia coli: a highly exposed active site conferring broad substrate specificity.

Journal: The Journal of biological chemistry 20061013

Title: Isolation and characterization of a novel poly(vinyl alcohol)-degrading bacterium, Sphingopyxis sp. PVA3.

Journal: Applied microbiology and biotechnology 20061001

Title: Detection of V-type nerve agent degradation products at electrodes modified by PPy/PQQ using CaCl2 as supporting electrolyte.

Journal: Analytical and bioanalytical chemistry 20060701

Title: Neuroprotection by pyrroloquinoline quinone (PQQ) in reversible middle cerebral artery occlusion in the adult rat.

Journal: Brain research 20060613

Title: Crystallization of quinoprotein glucose dehydrogenase variants and homologues by microseeding.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20060601

Title: Comparison of pyrroloquinoline quinone and/or metoprolol on myocardial infarct size and mitochondrial damage in a rat model of ischemia/reperfusion injury.

Journal: Journal of cardiovascular pharmacology and therapeutics 20060601

Title: Correlation between acetic acid resistance and characteristics of PQQ-dependent ADH in acetic acid bacteria.

Journal: Applied microbiology and biotechnology 20060401

Title: The 1.6A X-ray structure of the unusual c-type cytochrome, cytochrome cL, from the methylotrophic bacterium Methylobacterium extorquens.

Journal: Journal of molecular biology 20060317

Title: Pyrroloquinoline quinone-dependent dehydrogenases from Ketogulonicigenium vulgare catalyze the direct conversion of L-sorbosone to L-ascorbic acid.

Journal: Applied and environmental microbiology 20060201

Title: Structure of the pyrroloquinoline quinone radical in quinoprotein ethanol dehydrogenase.

Journal: The Journal of biological chemistry 20060120

Title: Peritoneal dialysis: a primary care perspective.

Journal: Journal of the American Board of Family Medicine : JABFM 20060101

Title: Transient formation of a neutral ubisemiquinone radical and subsequent intramolecular electron transfer to pyrroloquinoline quinone in the Escherichia coli membrane-integrated glucose dehydrogenase.

Journal: Biochemistry 20051018

Title: Molecular cloning and structural analysis of quinohemoprotein alcohol dehydrogenase ADH-IIG from Pseudomonas putida HK5.

Journal: Journal of molecular biology 20050909

Title: Reconstitution of apo-glucose dehydrogenase on pyrroloquinoline quinone-functionalized au nanoparticles yields an electrically contacted biocatalyst.

Journal: Journal of the American Chemical Society 20050907

Title: Pyrroloquinoline quinone enhances regeneration of transected sciatic nerve in rats.

Journal: Chinese journal of traumatology = Zhonghua chuang shang za zhi 20050801

Title: Oxidative cascades: a facile biosynthetic strategy for the assembly of complex molecules.

Journal: Bioorganic chemistry 20050601

Title: Molecular properties of membrane-bound FAD-containing D-sorbitol dehydrogenase from thermotolerant Gluconobacter frateurii isolated from Thailand.

Journal: Bioscience, biotechnology, and biochemistry 20050601

Title: Development of a novel glucose enzyme fuel cell system employing protein engineered PQQ glucose dehydrogenase.

Journal: Biosensors & bioelectronics 20050415

Title: Direct electrochemistry of heme multicofactor-containing enzymes on alkanethiol-modified gold electrodes.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20050401

Title: Magnetic field effects on bioelectrocatalytic reactions of surface-confined enzyme systems: enhanced performance of biofuel cells.

Journal: Journal of the American Chemical Society 20050323

Title: Cloning and characterization of a novel human homolog* of mouse U26, a putative PQQ-dependent AAS dehydrogenase.

Journal: Molecular biology reports 20050301

Title: Biochemistry: is pyrroloquinoline quinone a vitamin?

Journal: Nature 20050203

Title: Biochemistry: role of PQQ as a mammalian enzyme cofactor?

Journal: Nature 20050203

Title: Cyclization mechanism for the synthesis of macrocyclic antibiotic lankacidin in Streptomyces rochei.

Journal: Chemistry & biology 20050201

Title: Electrochemical determination of thiols at single-wall carbon nanotubes and PQQ modified electrodes.

Journal: Frontiers in bioscience : a journal and virtual library 20050101

Title: The atomic resolution structure of methanol dehydrogenase from Methylobacterium extorquens.

Journal: Acta crystallographica. Section D, Biological crystallography 20050101

Title: Increasing stability of water-soluble PQQ glucose dehydrogenase by increasing hydrophobic interaction at dimeric interface.

Journal: BMC biochemistry 20050101

Title: Enhanced rat sciatic nerve regeneration through silicon tubes filled with pyrroloquinoline quinone.

Journal: Microsurgery 20050101

Title: Wiring of PQQ-dehydrogenases.

Journal: Biosensors & bioelectronics 20041215

Title: Quinate oxidation in Gluconobacter oxydans IFO3244: purification and characterization of quinoprotein quinate dehydrogenase.

Journal: FEMS microbiology letters 20041215

Title: Degradation pathway of 2-chloroethanol in Pseudomonas stutzeri strain JJ under denitrifying conditions.

Journal: Archives of microbiology 20041201

Title: Pyrroloquinoline quinone (PQQ) decreases myocardial infarct size and improves cardiac function in rat models of ischemia and ischemia/reperfusion.

Journal: Cardiovascular drugs and therapy 20041101

Title: The quinoprotein dehydrogenases for methanol and glucose.

Journal: Archives of biochemistry and biophysics 20040801

Title: Quinohemoprotein alcohol dehydrogenases: structure, function, and physiology.

Journal: Archives of biochemistry and biophysics 20040801

Title: Electron transfer in quinoproteins.

Journal: Archives of biochemistry and biophysics 20040801

Title: Hydrogen tunneling in quinoproteins.

Journal: Archives of biochemistry and biophysics 20040801

Title: Molecular engineering of PQQGDH and its applications.

Journal: Archives of biochemistry and biophysics 20040801

Title: The structure of a biosynthetic intermediate of pyrroloquinoline quinone (PQQ) and elucidation of the final step of PQQ biosynthesis.

Journal: Journal of the American Chemical Society 20040505

Title: Characterisation of the PQQ cofactor radical in quinoprotein ethanol dehydrogenase of Pseudomonas aeruginosa by electron paramagnetic resonance spectroscopy.

Journal: FEBS letters 20040423

Title: Synthesis of imidazolo analogues of the oxidation-reduction cofactor pyrroloquinoline quinone (PQQ).

Journal: The Journal of organic chemistry 20040402

Title: Effect of green tea on blood glucose levels and serum proteomic patterns in diabetic (db/db) mice and on glucose metabolism in healthy humans.

Journal: BMC pharmacology 20040101

Title: [The PQQ-dehydrogenases. A novel example of bacterial quinoproteins].

Journal: Revista latinoamericana de microbiologia 20040101

Title: Cloning and expression of pyrroloquinoline quinone (PQQ) genes from a phosphate-solubilizing bacterium Enterobacter intermedium.

Journal: Current microbiology 20031201

Title: Purification and characterization of membrane-bound quinoprotein quinate dehydrogenase.

Journal: Bioscience, biotechnology, and biochemistry 20031001

Title: 3-dehydroquinate production by oxidative fermentation and further conversion of 3-dehydroquinate to the intermediates in the shikimate pathway.

Journal: Bioscience, biotechnology, and biochemistry 20031001

Title: Surface charge engineering of PQQ glucose dehydrogenase for downstream processing.

Journal: Biotechnology letters 20031001

Title: Electrochemical behavior of pyrroloquinoline quinone immobilized on silica gel modified with zirconium oxide.

Journal: Journal of colloid and interface science 20030701

Title: A biofuel cell with electrochemically switchable and tunable power output.

Journal: Journal of the American Chemical Society 20030604

Title: Glucose enzyme electrode using cytochrome b(562) as an electron mediator.

Journal: Biosensors & bioelectronics 20030501

Title: Nutritional biochemistry: A new redox-cofactor vitamin for mammals.

Journal: Nature 20030424

Title: New quinoproteins in oxidative fermentation.

Journal: Biochimica et biophysica acta 20030411

Title: The structure and mechanism of methanol dehydrogenase.

Journal: Biochimica et biophysica acta 20030411

Title: The ethanol oxidation system and its regulation in Pseudomonas aeruginosa.

Journal: Biochimica et biophysica acta 20030411

Title: The quinohaemoprotein lupanine hydroxylase from Pseudomonas putida.

Journal: Biochimica et biophysica acta 20030411

Title: Structure and mechanism of soluble glucose dehydrogenase and other PQQ-dependent enzymes.

Journal: Biochimica et biophysica acta 20030411

Title: Escherichia coli PQQ-containing quinoprotein glucose dehydrogenase: its structure comparison with other quinoproteins.

Journal: Biochimica et biophysica acta 20030411

Title: Research on the metabolic engineering of the direct oxidation pathway for extraction of phosphate from ore has generated preliminary evidence for PQQ biosynthesis in Escherichia coli as well as a possible role for the highly conserved region of quinoprotein dehydrogenases.

Journal: Biochimica et biophysica acta 20030411

Title: Deuterium isotope effect on enantioselectivity in the Comamonas testosteroni quinohemoprotein alcohol dehydrogenase-catalyzed kinetic resolution of rac-2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane, solketal.

Journal: Biochimica et biophysica acta 20030411

Title: The role of the MxaD protein in the respiratory chain of Methylobacterium extorquens during growth on methanol.

Journal: Biochimica et biophysica acta 20030411

Title: Effects of multiple ligand binding on kinetic isotope effects in PQQ-dependent methanol dehydrogenase.

Journal: Biochemistry 20030408

Title: Promoters and transcripts for genes involved in methanol oxidation in Methylobacterium extorquens AM1.

Journal: Microbiology (Reading, England) 20030401

Title: Pyrroloquinoline quinone improves growth and reproductive performance in mice fed chemically defined diets.

Journal: Experimental biology and medicine (Maywood, N.J.) 20030201

Title: New developments in oxidative fermentation.

Journal: Applied microbiology and biotechnology 20030201

Title: Involvement of a quinoprotein (PQQ-containing) alcohol dehydrogenase in the degradation of polypropylene glycols by the bacterium Stenotrophomonas maltophilia.

Journal: FEMS microbiology letters 20030128

Title: Antioxidant and pro-oxidant properties of pyrroloquinoline quinone (PQQ): implications for its function in biological systems.

Journal: Biochemical pharmacology 20030101

Title: Electrical contacting of flavoenzymes and NAD(P)+-dependent enzymes by reconstitution and affinity interactions on phenylboronic acid monolayers associated with Au-electrodes.

Journal: Journal of the American Chemical Society 20021211

Title: Escherichia coli and its application in a mediated amperometric glucose sensor.

Journal: Biosensors & bioelectronics 20021201

Title: PqqC/D, which converts a biosynthetic intermediate to pyrroloquinoline quinone.

Journal: Biochemical and biophysical research communications 20021129

Title: Cloning, sequencing and heterologous expression of the gene for lupanine hydroxylase, a quinocytochrome c from a Pseudomonas sp.

Journal: The Biochemical journal 20021015

Title: Magneto-switchable electrocatalytic and bioelectrocatalytic transformations.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20020916

Title: Electrical contacting of glucose dehydrogenase by the reconstitution of a pyrroloquinoline quinone-functionalized polyaniline film associated with an Au-electrode: an in situ electrochemical SPR study.

Journal: Chemical communications (Cambridge, England) 20020907

Title: The essential nutrient pyrroloquinoline quinone may act as a neuroprotectant by suppressing peroxynitrite formation.

Journal: The European journal of neuroscience 20020901

Title: Structure at 1.9 A resolution of a quinohemoprotein alcohol dehydrogenase from Pseudomonas putida HK5.

Journal: Structure (London, England : 1993) 20020601

Title: Determination of thiols by capillary electrophoresis with amperometric detection at a coenzyme pyrroloquinoline quinone modified electrode.

Journal: Analytical chemistry 20020315

Title: Electrical contacting of glucose oxidase by surface-reconstitution of the apo-protein on a relay-boronic acid-FAD cofactor monolayer.

Journal: Journal of the American Chemical Society 20020313

Title: Crystal structure of quinohemoprotein alcohol dehydrogenase from Comamonas testosteroni: structural basis for substrate oxidation and electron transfer.

Journal: The Journal of biological chemistry 20020201

Title: Molecular cloning and functional expression of D-sorbitol dehydrogenase from Gluconobacter suboxydans IF03255, which requires pyrroloquinoline quinone and hydrophobic protein SldB for activity development in E. coli.

Journal: Bioscience, biotechnology, and biochemistry 20020201

Title: L-erythrulose production by oxidative fermentation is catalyzed by PQQ-containing membrane-bound dehydrogenase.

Journal: Bioscience, biotechnology, and biochemistry 20020201

Title: Quinoproteins: structure, function, and biotechnological applications.

Journal: Applied microbiology and biotechnology 20020101

Title: Purification and characterization of membrane-bound quinoprotein cyclic alcohol dehydrogenase from Gluconobacter frateurii CHM 9.

Journal: Bioscience, biotechnology, and biochemistry 20011201

Title: Crystallization of quinohaemoprotein alcohol dehydrogenase from Comamonas testosteroni: crystals with unique optical properties.

Journal: Acta crystallographica. Section D, Biological crystallography 20011101

Title: Self-powered enzyme-based biosensors.

Journal: Journal of the American Chemical Society 20011031

Title: Pyrroloquinoline quinone (PQQ) and quinoprotein enzymes.

Journal: Antioxidants & redox signaling 20011001

Title: Site-directed mutagenesis and X-ray crystallography of the PQQ-containing quinoprotein methanol dehydrogenase and its electron acceptor, cytochrome c(L).

Journal: Biochemistry 20010821

Title: Ca(2+) stabilizes the semiquinone radical of pyrroloquinoline quinone.

Journal: The Biochemical journal 20010801

Title: Periplasmic PQQ-dependent glucose oxidation in free-living and symbiotic rhizobia.

Journal: Current microbiology 20010501

Title: An inducible 1-butanol dehydrogenase, a quinohaemoprotein, is involved in the oxidation of butane by 'Pseudomonas butanovora'.

Journal: Microbiology (Reading, England) 20010301

Title: Pyrroloquinoline quinone (PQQ) from methanol dehydrogenase and tryptophan tryptophylquinone (TTQ) from methylamine dehydrogenase.

Journal: Advances in protein chemistry 20010101

Title: Cofactor diversity in biological oxidations: implications and applications.

Journal: Chemical record (New York, N.Y.) 20010101

Title: Lupanine hydroxylase, a quinocytochrome c from an alkaloid-degrading Pseudomonas sp.

Journal: The Biochemical journal 19911001

Title: Moog RS, et al. Evidence for methoxatin (pyrroloquinolinequinone) as the cofactor in bovine plasma amine oxidase from resonance Raman spectroscopy. Proc Natl Acad Sci U S A. 1986 Nov;83(22):8435-9.

Title: Bishop A, et al. Methoxatin (PQQ) in guinea-pig neutrophils. Free Radic Biol Med. 1994 Oct;17(4):311-20.

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Tags:72909-34-3 Molecular Formula|72909-34-3 MDL|72909-34-3 SMILES|72909-34-3 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid