4433-40-3 | 5-Hydroxymethyluracil

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$8.00	$5.00
5g	97%	in stock	$10.00	$7.00
10g	97%	in stock	$13.00	$9.00
25g	97%	in stock	$29.00	$20.00
100g	97%	in stock	$112.00	$78.00

Description

• Catalog Number: AB69318
• Chemical Name: 5-Hydroxymethyluracil
• CAS Number: 4433-40-3
• Molecular Formula: C5H6N2O3
• Molecular Weight: 142.1127
• MDL Number: MFCD00056024
• SMILES: OCC1C=NC(=O)NC1=O
• NSC Number: 20901

Computed Properties

• Complexity: 209
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 1
• XLogP3: -1.9

Literature

• Profiling cytosine oxidation in DNA by LC-MS/MS.

  Chemical research in toxicology 20120917

• Discovery of novel 5-(ethyl or hydroxymethyl) analogs of 2'-'up' fluoro (or hydroxyl) pyrimidine nucleosides as a new class of Mycobacterium tuberculosis, Mycobacterium bovis and Mycobacterium avium inhibitors.

  Bioorganic & medicinal chemistry 20120701

• Biochemical characterization of recombinant β-glucosyltransferase and analysis of global 5-hydroxymethylcytosine in unique genomes.

  Biochemistry 20120207

• DNA glycosylases: in DNA repair and beyond.

  Chromosoma 20120201

• Identifying and characterizing alternative molecular markers for the symbiotic and free-living dinoflagellate genus Symbiodinium.

  PloS one 20120101

• Symbiodinium transcriptomes: genome insights into the dinoflagellate symbionts of reef-building corals.

  PloS one 20120101

• Thymine DNA glycosylase is essential for active DNA demethylation by linked deamination-base excision repair.

  Cell 20110708

• Inactivation of the DNA repair genes mutS, mutL or the anti-recombination gene mutS2 leads to activation of vitamin B1 biosynthesis genes.

  PloS one 20110101

• Recombination phenotypes of the NCI-60 collection of human cancer cells.

  BMC molecular biology 20110101

• Severe encephalopathy, lactic acidosis, vegetative instability and neuropathy with 5-Fluorouracil treatment - pyrimidine degradation defect or beriberi?

  Case reports in oncology 20110101

• Increased oxidative/nitrosative stress markers measured non- invasively in patients with high 2,3,7,8-tetrachloro-dibenzo-p-dioxin plasma level.

  Neuro endocrinology letters 20110101

• Direct detection and sequencing of damaged DNA bases.

  Genome integrity 20110101

• Domain swapping in allosteric modulation of DNA specificity.

  PLoS biology 20101201

• Opposite effects of 5-hydroxymethyluracil on mitogenic response of T cells stimulated through T-cell receptor or through T-cell receptor and CD28 co-receptor molecule.

  Bulletin of experimental biology and medicine 20101201

• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

  Bioorganic & medicinal chemistry letters 20101101

• CyDNA: synthesis and replication of highly Cy-dye substituted DNA by an evolved polymerase.

  Journal of the American Chemical Society 20100414

• Biosynthesis and molecular genetics of polyketides in marine dinoflagellates.

  Marine drugs 20100101

• Stimulation of DNA Glycosylase Activities by XPC Protein Complex: Roles of Protein-Protein Interactions.

  Journal of nucleic acids 20100101

• Early Steps in the DNA Base Excision Repair Pathway of a Fission Yeast Schizosaccharomyces pombe.

  Journal of nucleic acids 20100101

• Error-Prone Translesion DNA Synthesis by Escherichia coli DNA Polymerase IV (DinB) on Templates Containing 1,2-dihydro-2-oxoadenine.

  Journal of nucleic acids 20100101

• Tissue distribution of 5-hydroxymethylcytosine and search for active demethylation intermediates.

  PloS one 20100101

• Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine.

  Journal of clinical biochemistry and nutrition 20091101

• Thymine hydroperoxide as a potential source of singlet molecular oxygen in DNA.

  Free radical biology & medicine 20090815

• Classification of Myoviridae bacteriophages using protein sequence similarity.

  BMC microbiology 20090101

• Generation of thymine radicals from 6-alkoxy-5-bromo-5,6-dihydrothymine derivatives by radiolytic reduction and photolytic dehalogenation.

  Chemical research in toxicology 20080401

• Hepatic oxidative DNA damage is associated with increased risk for hepatocellular carcinoma in chronic hepatitis C.

  British journal of cancer 20080212

• Measurement of the incorporation and repair of exogenous 5-hydroxymethyl-2'-deoxyuridine in human cells in culture using gas chromatography-negative chemical ionization-mass spectrometry.

  Chemical research in toxicology 20071201

• Recombinant Schizosaccharomyces pombe Nth1 protein exhibits DNA glycosylase activities for 8-oxo-7,8-dihydroguanine and thymine residues oxidized in the methyl group.

  Journal of radiation research 20070901

• Ab initio base-pairing energies of an oxidized thymine product, 5-formyluracil, with standard DNA bases at the BSSE-free DFT and MP2 theory levels.

  Organic & biomolecular chemistry 20070521

• Experimental study of hepatoprotective activity of hydroxymethyluracil.

  Bulletin of experimental biology and medicine 20070501

• Correction of morphological shifts in experimental syringomyelia.

  Bulletin of experimental biology and medicine 20070501

• DNA-uracil and human pathology.

  Molecular aspects of medicine 20070101

• Formamide as the main building block in the origin of nucleic acids.

  BMC evolutionary biology 20070101

• A new protein superfamily includes two novel 3-methyladenine DNA glycosylases from Bacillus cereus, AlkC and AlkD.

  Molecular microbiology 20060301

• DNA polymerase lambda protects mouse fibroblasts against oxidative DNA damage and is recruited to sites of DNA damage/repair.

  The Journal of biological chemistry 20050909

• Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct.

  Toxicology letters 20050315

• Organization of the genome and gene expression in a nuclear environment lacking histones and nucleosomes: the amazing dinoflagellates.

  European journal of cell biology 20050301

• Repair of oxidative damage of thymine by HeLa whole-cell extracts: simultaneous analysis using a microsupport and comparison with traditional PAGE analysis.

  Biochimie 20050201

• DNA glycosylase activities for thymine residues oxidized in the methyl group are functions of the hNEIL1 and hNTH1 enzymes in human cells.

  DNA repair 20050102

• Urinary excretion of DNA repair products correlates with metabolic rates as well as with maximum life spans of different mammalian species.

  Free radical biology & medicine 20041101

• Diet is not responsible for the presence of several oxidatively damaged DNA lesions in mouse urine.

  Free radical research 20041101

• Qualitative and quantitative analyses of the decomposition products that arise from the exposure of thymine to monochromatic ultrasoft X rays and 60Co gamma rays in the solid state.

  Radiation research 20040401

• Base J, found in nuclear DNA of Trypanosoma brucei, is not a target for DNA glycosylases.

  DNA repair 20040203

• Radiation-induced DNA damage: formation, measurement, and biochemical features.

  Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer 20040101

• [Hydroxymethyluracil in the correction of adverse effects caused by chemotherapy of malignant neoplasms].

  Eksperimental'naia i klinicheskaia farmakologiia 20040101

• Cellular and molecular mechanisms in environmental and occupational inhalation toxicology.

  GMS current topics in otorhinolaryngology, head and neck surgery 20040101

• The transcription factor, NFI/CTF plays a positive regulatory role in expression of the hSMUG1 gene.

  DNA repair 20031209

• Surface salt bridges modulate DNA wrapping by the type II DNA-binding protein TF1.

  Biochemistry 20030729

• Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030715

• Mismatch uracil glycosylase from Escherichia coli: a general mismatch or a specific DNA glycosylase?

  The Journal of biological chemistry 20030606

• Structure and specificity of the vertebrate anti-mutator uracil-DNA glycosylase SMUG1.

  Molecular cell 20030601

• Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA.

  Biochemistry 20030506

• Mammalian 5-formyluracil-DNA glycosylase. 2. Role of SMUG1 uracil-DNA glycosylase in repair of 5-formyluracil and other oxidized and deaminated base lesions.

  Biochemistry 20030506

• Identification and characterization of mammalian 5-formyluracil-DNA glycosylase.

  Nucleic acids research. Supplement (2001) 20030101

• hUNG2 is the major repair enzyme for removal of uracil from U:A matches, U:G mismatches, and U in single-stranded DNA, with hSMUG1 as a broad specificity backup.

  The Journal of biological chemistry 20021018

• Repair of deaminated bases in DNA.

  Free radical biology & medicine 20021001

• Endogenous DNA lesions can inhibit the binding of the AP-1 (c-Jun) transcription factor.

  Biochemistry 20020625

• The role of surface-exposed lysines in wrapping DNA about the bacterial histone-like protein HU.

  Biochemistry 20020618

• Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity.

  Chemical research in toxicology 20020101

• Kinetic analysis of nucleotides incorporated opposite oxidized thymine bases on template DNA.

  Nucleic acids research. Supplement (2001) 20020101

• Definitive identification of mammalian 5-hydroxymethyluracil DNA N-glycosylase activity as SMUG1.

  The Journal of biological chemistry 20011109

• High-affinity DNA binding of HU protein from the hyperthermophile Thermotoga maritima.

  Journal of molecular biology 20010817

• Role of the Escherichia coli and human DNA glycosylases that remove 5-formyluracil from DNA in the prevention of mutations.

  Journal of radiation research 20010301

• 5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism.

  Toxicology letters 20010203

• Excessive base excision repair of 5-hydroxymethyluracil from DNA induces apoptosis in Chinese hamster V79 cells containing mutant p53.

  Carcinogenesis 20010101

• Long term adaptation of a microbial population to a permanent metabolic constraint: overcoming thymineless death by experimental evolution of Escherichia coli.

  BMC biotechnology 20010101

• Binding activity of replication protein A to single-stranded DNA containing oxidized pyrimidine base.

  Nucleic acids research. Supplement (2001) 20010101