1946-82-3 | Ac-Lys-OH

Packsize	Purity	Availability	Price	Discounted Price
250mg	98%	in stock	$6.00	$4.00
1g	98%	in stock	$11.00	$8.00
5g	98%	in stock	$46.00	$33.00
25g	98%	in stock	$192.00	$134.00
100g	98%	in stock	$667.00	$467.00

Description

• Catalog Number: AB42963
• Chemical Name: Ac-Lys-OH
• CAS Number: 1946-82-3
• Molecular Formula: C8H16N2O3
• Molecular Weight: 188.2242
• MDL Number: MFCD00008233
• SMILES: CC(=O)N[C@H](C(=O)O)CCCCN

Computed Properties

• Complexity: 182
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 6
• XLogP3: -4.4

Literature

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  Journal of theoretical biology 20121007

• Aurora B is regulated by acetylation/deacetylation during mitosis in prostate cancer cells.

  FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20121001

• Druggability analysis and structural classification of bromodomain acetyl-lysine binding sites.

  Journal of medicinal chemistry 20120913

• Lysine acetylation is widespread on proteins of diverse function and localization in the protozoan parasite Toxoplasma gondii.

  Eukaryotic cell 20120601

• Myc proteins in brain tumor development and maintenance.

  Upsala journal of medical sciences 20120501

• Untargeted metabolomics reveals a lack of synergy between nifurtimox and eflornithine against Trypanosoma brucei.

  PLoS neglected tropical diseases 20120501

• Non-histone lysine acetylated proteins in heart failure.

  Biochimica et biophysica acta 20120401

• Is histone acetylation the most important physiological function for CBP and p300?

  Aging 20120401

• Histone recognition and large-scale structural analysis of the human bromodomain family.

  Cell 20120330

• N-acetyl lysyl-tRNA synthetases evolved by a CcdB-based selection possess N-acetyl lysine specificity in vitro and in vivo.

  FEBS letters 20120323

• Modulatory effect of resveratrol on SIRT1, SIRT3, SIRT4, PGC1α and NAMPT gene expression profiles in wild-type adult zebrafish liver.

  Molecular biology reports 20120301

• Trapping of cis-2-butene-1,4-dial to measure furan metabolism in human liver microsomes by cytochrome P450 enzymes.

  Drug metabolism and disposition: the biological fate of chemicals 20120301

• SirT1 catalytic activity is required for male fertility and metabolic homeostasis in mice.

  FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20120201

• Fragment-based discovery of bromodomain inhibitors part 2: optimization of phenylisoxazole sulfonamides.

  Journal of medicinal chemistry 20120126

• SIRT1 contains N- and C-terminal regions that potentiate deacetylase activity.

  The Journal of biological chemistry 20120120

• Dual modification of Alzheimer's disease PHF-tau protein by lysine methylation and ubiquitylation: a mass spectrometry approach.

  Acta neuropathologica 20120101

• Two lysines in the forkhead domain of foxp3 are key to T regulatory cell function.

  PloS one 20120101

• Increasing dietary fat elicits similar changes in fat oxidation and markers of muscle oxidative capacity in lean and obese humans.

  PloS one 20120101

• Sirtuins and disease: the road ahead.

  Frontiers in pharmacology 20120101

• Structures, substrates, and regulators of Mammalian sirtuins - opportunities and challenges for drug development.

  Frontiers in pharmacology 20120101

• Transcriptional repressor NIR functions in the ribosome RNA processing of both 40S and 60S subunits.

  PloS one 20120101

• Cross-talk between phosphorylation and lysine acetylation in a genome-reduced bacterium.

  Molecular systems biology 20120101

• Arsenic trioxide exerts antimyeloma effects by inhibiting activity in the cytoplasmic substrates of histone deacetylase 6.

  PloS one 20120101

• Function of the active site lysine autoacetylation in Tip60 catalysis.

  PloS one 20120101

• Inhibition of SIRT1 impairs the accumulation and transcriptional activity of HIF-1α protein under hypoxic conditions.

  PloS one 20120101

• Resveratrol mediated modulation of Sirt-1/Runx2 promotes osteogenic differentiation of mesenchymal stem cells: potential role of Runx2 deacetylation.

  PloS one 20120101

• Identifying acetylated proteins in mitosis.

  Methods in molecular biology (Clifton, N.J.) 20120101

• Structure, mechanism, and inhibition of histone deacetylases and related metalloenzymes.

  Current opinion in structural biology 20111201

• Progress in the discovery of small-molecule inhibitors of bromodomain--histone interactions.

  Journal of biomolecular screening 20111201

• Druggability of methyl-lysine binding sites.

  Journal of computer-aided molecular design 20111201

• Metabolic variation during development in culture of Leishmania donovani promastigotes.

  PLoS neglected tropical diseases 20111201

• The opposing transcriptional functions of Sin3a and c-Myc are required to maintain tissue homeostasis.

  Nature cell biology 20111120

• Aspirin acetylates multiple cellular proteins in HCT-116 colon cancer cells: Identification of novel targets.

  International journal of oncology 20111101

• Chromatin affinity purification and quantitative mass spectrometry defining the interactome of histone modification patterns.

  Molecular & cellular proteomics : MCP 20111101

• Repressive LTR nucleosome positioning by the BAF complex is required for HIV latency.

  PLoS biology 20111101

• 3,5-dimethylisoxazoles act as acetyl-lysine-mimetic bromodomain ligands.

  Journal of medicinal chemistry 20111013

• Inhibition of BET recruitment to chromatin as an effective treatment for MLL-fusion leukaemia.

  Nature 20111002

• BET bromodomain inhibition as a therapeutic strategy to target c-Myc.

  Cell 20110916

• Bromodomains as therapeutic targets.

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• Curcumin modulates nuclear factor kappaB (NF-kappaB)-mediated inflammation in human tenocytes in vitro: role of the phosphatidylinositol 3-kinase/Akt pathway.

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  Aging 20110601

• Identification of a sudden cardiac death susceptibility locus at 2q24.2 through genome-wide association in European ancestry individuals.

  PLoS genetics 20110601

• TRAF6 ubiquitinates TGFβ type I receptor to promote its cleavage and nuclear translocation in cancer.

  Nature communications 20110501

• Preparation of fully synthetic histone H3 reveals that acetyl-lysine 56 facilitates protein binding within nucleosomes.

  Journal of molecular biology 20110429

• A small molecule binding to the coactivator CREB-binding protein blocks apoptosis in cardiomyocytes.

  Chemistry & biology 20110422

• CLU blocks HDACI-mediated killing of neuroblastoma.

  Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine 20110401

• Resveratrol-mediated SIRT-1 interactions with p300 modulate receptor activator of NF-kappaB ligand (RANKL) activation of NF-kappaB signaling and inhibit osteoclastogenesis in bone-derived cells.

  The Journal of biological chemistry 20110401

• The path to clinical proteomics research: integration of proteomics, genomics, clinical laboratory and regulatory science.

  The Korean journal of laboratory medicine 20110401

• Capillary electrophoresis-based sirtuin assay using non-peptide substrates.

  Journal of pharmaceutical and biomedical analysis 20110325

• hALP, a novel transcriptional U three protein (t-UTP), activates RNA polymerase I transcription by binding and acetylating the upstream binding factor (UBF).

  The Journal of biological chemistry 20110304

• Enhanced reactivity of Lys182 explains the limited efficacy of biogenic amines in preventing the inactivation of glucose-6-phosphate dehydrogenase by methylglyoxal.

  Bioorganic & medicinal chemistry 20110301

• H3 lysine 4 is acetylated at active gene promoters and is regulated by H3 lysine 4 methylation.

  PLoS genetics 20110301

• Rational design of cyclic peptide modulators of the transcriptional coactivator CBP: a new class of p53 inhibitors.

  Journal of the American Chemical Society 20110223

• SIRT3 substrate specificity determined by peptide arrays and machine learning.

  ACS chemical biology 20110218

• Mitochondrial biogenesis and peroxisome proliferator-activated receptor-γ coactivator-1α (PGC-1α) deacetylation by physical activity: intact adipocytokine signaling is required.

  Diabetes 20110101

• Structure of Sir2Tm bound to a propionylated peptide.

  Protein science : a publication of the Protein Society 20110101

• Histone deacetylase inhibitors: the epigenetic therapeutics that repress hypoxia-inducible factors.

  Journal of biomedicine & biotechnology 20110101

• Manipulating protein acetylation in breast cancer: a promising approach in combination with hormonal therapies?

  Journal of biomedicine & biotechnology 20110101

• Histone H4 lysine 12 acetylation regulates telomeric heterochromatin plasticity in Saccharomyces cerevisiae.

  PLoS genetics 20110101

• Histone deacetylase activity modulates alternative splicing.

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• The biology of lysine acetylation integrates transcriptional programming and metabolism.

  Nutrition & metabolism 20110101

• Neuronal Sirt3 protects against excitotoxic injury in mouse cortical neuron culture.

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• Mitochondrial acetylation and diseases of aging.

  Journal of aging research 20110101

• Post-translational protein modification by carotenoid cleavage products.

  BioFactors (Oxford, England) 20110101

• Characterization of DXZ4 conservation in primates implies important functional roles for CTCF binding, array expression and tandem repeat organization on the X chromosome.

  Genome biology 20110101

• Rapid temporal control of Foxp3 protein degradation by sirtuin-1.

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  PloS one 20110101

• The intensity of IUGR-induced transcriptome deregulations is inversely correlated with the onset of organ function in a rat model.

  PloS one 20110101

• Tip60-mediated acetylation activates transcription independent apoptotic activity of Abl.

  Molecular cancer 20110101

• Quercetin suppresses cyclooxygenase-2 expression and angiogenesis through inactivation of P300 signaling.

  PloS one 20110101

• Succinate dehydrogenase is a direct target of sirtuin 3 deacetylase activity.

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• K-acetylation and its enzymes: overview and new developments.

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• Acetylation of the proto-oncogene EVI1 abrogates Bcl-xL promoter binding and induces apoptosis.

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• Regulation of septin dynamics by the Saccharomyces cerevisiae lysine acetyltransferase NuA4.

  PloS one 20110101

• Sirt3, mitochondrial ROS, ageing, and carcinogenesis.

  International journal of molecular sciences 20110101

• SUMOylation of the Forkhead transcription factor FOXL2 promotes its stabilization/activation through transient recruitment to PML bodies.

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• Drug discovery toward antagonists of methyl-lysine binding proteins.

  Current chemical genomics 20110101

• Smyd1b_tv1, a key regulator of sarcomere assembly, is localized on the M-line of skeletal muscle fibers.

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• IGF-1 and PDGF-bb suppress IL-1β-induced cartilage degradation through down-regulation of NF-κB signaling: involvement of Src/PI-3K/AKT pathway.

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• Selective inhibition of BET bromodomains.

  Nature 20101223

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  Medicinal research reviews 20101101

• Autoacetylation of the Ralstonia solanacearum effector PopP2 targets a lysine residue essential for RRS1-R-mediated immunity in Arabidopsis.

  PLoS pathogens 20101101

• Simultaneous chemical and photochemical protein crosslinking induced by irradiation of eye lens proteins in the presence of ascorbate: the photosensitizing role of an UVA-visible-absorbing decomposition product of vitamin C.

  Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20101028

• Cell cycle-dependent acetylation of Rb2/p130 in NIH3T3 cells.

  Oncogene 20101021

• Structural genomics of histone tail recognition.

  Bioinformatics (Oxford, England) 20101015

• Identification of covalent binding sites of ethyl 2-cyanoacrylate, methyl methacrylate and 2-hydroxyethyl methacrylate in human hemoglobin using LC/MS/MS techniques.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20101001

• Reading chromatin: insights from yeast into YEATS domain structure and function.

  Epigenetics 20101001

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• NMR-based detection of acetylation sites in peptides.

  Journal of peptide science : an official publication of the European Peptide Society 20100801

• Site-specific introduction of an acetyl-lysine mimic into peptides and proteins by cysteine alkylation.

  Journal of the American Chemical Society 20100728

• Ability of hypochlorous acid and N-chloramines to chlorinate DNA and its constituents.

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• Mechanism and regulation of acetylated histone binding by the tandem PHD finger of DPF3b.

  Nature 20100708

• CobB regulates Escherichia coli chemotaxis by deacetylating the response regulator CheY.

  Molecular microbiology 20100601

• Protein acyltransferase function of purified calreticulin. Part 1: characterization of propionylation of protein utilizing propoxycoumarin as the propionyl group donor.

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• Nucleophosmin phosphorylation by v-cyclin-CDK6 controls KSHV latency.

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• Excessive HDAC activation is critical for neurodegeneration in the rd1 mouse.

  Cell death & disease 20100201

• Acetylation of p65 at lysine 314 is important for late NF-kappaB-dependent gene expression.

  BMC genomics 20100101

• Biochemical profiling of histone binding selectivity of the yeast bromodomain family.

  PloS one 20100101

• Identification of arginine- and lysine-methylation in the proteome of Saccharomyces cerevisiae and its functional implications.

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• Behaviour of 4-(-2-hydroxyethyl)-1-piperazineethanesulfonic acid under electrospray ionization mass spectrometry conditions.

  European journal of mass spectrometry (Chichester, England) 20100101

• GCN5-dependent acetylation of HIV-1 integrase enhances viral integration.

  Retrovirology 20100101

• Single cell analysis of transcriptional activation dynamics.

  PloS one 20100101

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  Archaea (Vancouver, B.C.) 20100101

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  Molecular cancer 20100101

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• Sex-biased transcription enhancement by a 5' tethered Gal4-MOF histone acetyltransferase fusion protein in Drosophila.

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• Identification and characterization of novel sirtuin inhibitor scaffolds.

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• Cooperative binding of two acetylation marks on a histone tail by a single bromodomain.

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• The role of human bromodomains in chromatin biology and gene transcription.

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• A mechanistic investigation into the irreversible protein binding and antigenicity of p-phenylenediamine.

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• Lacticin 481 synthetase as a general serine/threonine kinase.

  ACS chemical biology 20090515

• Autoacetylation of purified calreticulin transacetylase utilizing acetoxycoumarin as the acetyl group donor.

  Applied biochemistry and biotechnology 20090501

• Formation of mono- and bis-Michael adducts by the reaction of nucleophilic amino acids with hydroxymethylvinyl ketone, a reactive metabolite of 1,3-butadiene.

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  Analytical biochemistry 20090415

• Overexpression of SIRT1 protects pancreatic beta-cells against cytokine toxicity by suppressing the nuclear factor-kappaB signaling pathway.

  Diabetes 20090201

• Histone methylation sets the stage for meiotic DNA breaks.

  The EMBO journal 20090121

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  Toxicological sciences : an official journal of the Society of Toxicology 20090101

• The chromatin remodelling factor BRG1 is a novel binding partner of the tumor suppressor p16INK4a.

  Molecular cancer 20090101

• Computational screening of molecular targets in Plasmodium for novel non resistant anti-malarial drugs.

  Bioinformation 20090101

• Peptide microarrays for profiling of modification state-specific antibodies.

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  Retrovirology 20090101

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  PloS one 20090101

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  Journal of the American Chemical Society 20081210

• Establishment of glutamine synthetase of Mycobacterium smegmatis as a protein acetyltransferase utilizing polyphenolic acetates as the acetyl group donors.

  Journal of biochemistry 20081201

• Quantitative analysis of histone deacetylase-1 selective histone modifications by differential mass spectrometry.

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• Identification of plasma proteins that are susceptible to thiol oxidation by hypochlorous acid and N-chloramines.

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• Thermodynamic analysis of acetylation-dependent Pb1 bromodomain-histone H3 interactions.

  Analytical biochemistry 20080315

• In vivo acetylation of CheY, a response regulator in chemotaxis of Escherichia coli.

  Journal of molecular biology 20080307

• Biomarkers of furan exposure by metabolic profiling of rat urine with liquid chromatography-tandem mass spectrometry and principal component analysis.

  Chemical research in toxicology 20080301

• Creatine kinase-mediated ATP supply fuels actin-based events in phagocytosis.

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• SIRT1 inhibition alleviates gene silencing in Fragile X mental retardation syndrome.

  PLoS genetics 20080301

• Chemical properties of oxopropenyl adducts of purine and pyrimidine nucleosides and their reactivity toward amino acid cross-link formation.

  Journal of the American Chemical Society 20080220

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  BMC cell biology 20080101

• The BRG1 transcriptional coregulator.

  Nuclear receptor signaling 20080101

• Acetylation regulates WRN catalytic activities and affects base excision DNA repair.

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• Zebrafish brd2a and brd2b are paralogous members of the bromodomain-ET (BET) family of transcriptional coregulators that show structural and expression divergence.

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  Genome biology 20080101

• Tumor microvasculature: endothelial leakiness and endothelial pore size distribution in a breast cancer model.

  Breast cancer : basic and clinical research 20080101

• Acetyl-lysine analog peptides as mechanistic probes of protein deacetylases.

  The Journal of biological chemistry 20071221

• Mechanism-based inhibition of Sir2 deacetylases by thioacetyl-lysine peptide.

  Biochemistry 20071218

• The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates.

  Carbohydrate research 20071210

• Formation of three N-acetyl-L-cysteine monoadducts and one diadduct by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with N-acetyl-L-cysteine at physiological conditions: chemical mechanisms and toxicological implications.

  Chemical research in toxicology 20071001

• Characterization of Nalpha-benzyloxycarbonyl-L-lysine oxidizing enzyme from Rhodococcus sp. AIU Z-35-1.

  Journal of bioscience and bioengineering 20070901

• Structure and acetyl-lysine recognition of the bromodomain.

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  Toxicological sciences : an official journal of the Society of Toxicology 20070801

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• Structural ramification for acetyl-lysine recognition by the bromodomain of human BRG1 protein, a central ATPase of the SWI/SNF remodeling complex.

  Chembiochem : a European journal of chemical biology 20070723

• Multiple roles for acetylation in the interaction of p300 HAT with ATF-2.

  Biochemistry 20070717

• Sir2 deacetylases exhibit nucleophilic participation of acetyl-lysine in NAD+ cleavage.

  Journal of the American Chemical Society 20070509

• Polybromo-1-bromodomains bind histone H3 at specific acetyl-lysine positions.

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  Nature chemical biology 20070101

• Breast cancer metastasis suppressor 1 (BRMS1) inhibits osteopontin transcription by abrogating NF-kappaB activation.

  Molecular cancer 20070101

• Characterization of protein transacetylase from human placenta as a signaling molecule calreticulin using polyphenolic peracetates as the acetyl group donors.

  Cell biochemistry and biophysics 20070101

• Requirement of histone deacetylase activity for the expression of critical photoreceptor genes.

  BMC developmental biology 20070101

• Solution structure of the second bromodomain of Brd2 and its specific interaction with acetylated histone tails.

  BMC structural biology 20070101

• Expression, purification and characterization of individual bromodomains from human Polybromo-1.

  Protein expression and purification 20061101

• SWI/SNF displaces SAGA-acetylated nucleosomes.

  Eukaryotic cell 20061001

• Characterization of the amino acid adducts of the enedial derivative of teucrin A.

  Chemical research in toxicology 20061001

• Structural basis for D-amino acid transamination by the pyridoxal 5'-phosphate-dependent catalytic antibody 15A9.

  The Journal of biological chemistry 20060818

• Kinetics and mechanism of the addition of nucleophiles to alpha,beta-unsaturated thiol esters.

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• pH dependency of the carboxyl oxygen exchange reaction catalyzed by lysyl endopeptidase and trypsin.

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• Use of substrate analogs and mutagenesis to study substrate binding and catalysis in the Sir2 family of NAD-dependent protein deacetylases.

  The Journal of biological chemistry 20060428

• Sodium butyrate-mediated Sp3 acetylation represses human insulin-like growth factor binding protein-3 expression in intestinal epithelial cells.

  Journal of pediatric gastroenterology and nutrition 20060201

• The Epc-N domain: a predicted protein-protein interaction domain found in select chromatin associated proteins.

  BMC genomics 20060101

• Target structure-based discovery of small molecules that block human p53 and CREB binding protein association.

  Chemistry & biology 20060101

• Hydralazine target: from blood vessels to the epigenome.

  Journal of translational medicine 20060101

• Transcriptional regulation of metabotropic glutamate receptor 2/3 expression by the NF-kappaB pathway in primary dorsal root ganglia neurons: a possible mechanism for the analgesic effect of L-acetylcarnitine.

  Molecular pain 20060101

• Limited proteolysis of human histone deacetylase 1.

  BMC biochemistry 20060101

• DNA-binding properties of the recombinant high-mobility-group-like AT-hook-containing region from human BRG1 protein.

  Biological chemistry 20060101

• Proteomic analysis of organ-specific post-translational lysine-acetylation and -methylation in mice by use of anti-acetyllysine and -methyllysine mouse monoclonal antibodies.

  Proteomics 20051201

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  PLoS biology 20051201

• Unstructured conformations are a substrate requirement for the Sir2 family of NAD-dependent protein deacetylases.

  The Journal of biological chemistry 20051028

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  PLoS biology 20051001

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  The Journal of biological chemistry 20050610

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• Histone modifications: from genome-wide maps to functional insights.

  Genome biology 20050101

• Acetylation of the chemotaxis response regulator CheY by acetyl-CoA synthetase purified from Escherichia coli.

  Journal of molecular biology 20040910

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  Gene expression patterns : GEP 20040901

• Fluorescence assay of SIRT protein deacetylases using an acetylated peptide substrate and a secondary trypsin reaction.

  Analytical biochemistry 20040901

• Autoantibodies against N-homocysteinylated proteins in humans: implications for atherosclerosis.

  Stroke 20040601

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  The EMBO journal 20040324

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  Molecular cell 20040312

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  Rapid communications in mass spectrometry : RCM 20040101

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  BMC cell biology 20040101

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  Genome biology 20040101

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  BMC molecular biology 20040101

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  BMC biology 20040101

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  The Journal of biological chemistry 20031205

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  The EMBO journal 20031201

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  Structure (London, England : 1993) 20031101

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  Nature structural biology 20031001

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  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030505

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  Biochemistry 20030204

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  Journal of immunological methods 20030115

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  Journal of agricultural and food chemistry 20030101

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  Extremophiles : life under extreme conditions 20021201

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  Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20021001

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  Molecular cell 20020901

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  The Journal of biological chemistry 20020802

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  Chemical research in toxicology 20020601

• Bromodomain: an acetyl-lysine binding domain.

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  FEBS letters 20020213

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  Biochemistry 20020129

• The diversity of acetylated proteins.

  Genome biology 20020101

• Capillary electrophoretic separation by double-strand polyaniline-coate capillaries of the advanced glycation endproducts formed from N-alpha-acetyl-L-lysine with reducing sugars.

  Journal of capillary electrophoresis and microchip technology 20020101

• Structure of histone deacetylases: insights into substrate recognition and catalysis.

  Structure (London, England : 1993) 20011201

• Duality in bromodomain-containing protein complexes.

  Frontiers in bioscience : a journal and virtual library 20010801

• Acetyllysine-binding and function of bromodomain-containing proteins in chromatin.

  Frontiers in bioscience : a journal and virtual library 20010801

• The bromodomain: a chromatin browser?

  Frontiers in bioscience : a journal and virtual library 20010801

• The bromodomain: a regulator of ATP-dependent chromatin remodeling?

  Frontiers in bioscience : a journal and virtual library 20010801

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  The Journal of biological chemistry 20010406

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  Free radical biology & medicine 20010301

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  The Journal of biological chemistry 20010209

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  Journal of AOAC International 20010101