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2'-deoxyinosine
inosine, 2'-deoxy-

Supplier Sponsors

Name:9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
CAS Number: 890-38-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:212-964-1
FDA UNII: HN0RQ6SBWQ
Nikkaji Web:J128.131C
Beilstein Number:033517
MDL:MFCD00005762
XlogP3:-1.70 (est)
Molecular Weight:252.23044000
Formula:C10 H12 N4 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 3.25e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2'-Deoxyinosine ≥98% by HPLC
Santa Cruz Biotechnology
For experimental / research use only.
2'-Deoxyinosine ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
2-Deoxyinosine ≥98%
sds
TCI AMERICA
For experimental / research use only.
2'-Deoxyinosine >98.0%(HPLC)(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for 2'-deoxyinosine usage levels up to:
 not for fragrance use.
 
Recommendation for 2'-deoxyinosine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65058
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
Chemidplus:0000890380
 
References:
 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:890-38-0
Pubchem (cid):65058
Pubchem (cas):890-38-0
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C05512
HMDB (The Human Metabolome Database):HMDB00071
FooDB:FDB012323
YMDB (Yeast Metabolome Database):YMDB00659
Export Tariff Code:2934.99.4400
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bean green bean
Search Trop Picture
 
Synonyms:
(-)-2-deoxyinosine
9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
 inosine, 2'-deoxy-
 

Articles:

PubMed:Enzymatic synthesis of ribo- and 2'-deoxyribonucleosides from glycofuranosyl phosphates: An approach to facilitate isotopic labeling.
PubMed:Mutagenic Replication of N(2)-Deoxyguanosine Benzo[a]pyrene Adducts by Escherichia coli DNA Polymerase I and Sulfolobus solfataricus DNA Polymerase IV.
PubMed:Chemical modification improves the stability of the DNA aptamer GBI-10 and its affinity towards tenascin-C.
PubMed:A novel bis(pinacolato)diboron-mediated N-O bond deoxygenative route to C6 benzotriazolyl purine nucleoside derivatives.
PubMed:Bioactivity of 2'-deoxyinosine-incorporated aptamer AS1411.
PubMed:Chemical Constituents of Cordyceps cicadae.
PubMed:DNA Adduct Formation from Metabolic 5'-Hydroxylation of the Tobacco-Specific Carcinogen N'-Nitrosonornicotine in Human Enzyme Systems and in Rats.
PubMed:Comparative characterization of nucleotides, nucleosides and nucleobases in Abelmoschus manihot roots, stems, leaves and flowers during different growth periods by UPLC-TQ-MS/MS.
PubMed:Simultaneous quantification of purine and pyrimidine bases, nucleosides and their degradation products in bovine blood plasma by high performance liquid chromatography tandem mass spectrometry.
PubMed:NMR structure of an ethylene interstrand cross-linked DNA which mimics the lesion formed by 1,3-bis(2-chloroethyl)-1-nitrosourea.
PubMed:Biodistribution, tumor uptake and efficacy of 5-FU-loaded liposomes: why size matters.
PubMed:Fecal metabonomic study of a polysaccharide, MDG-1 from Ophiopogon japonicus on diabetic mice based on gas chromatography/time-of-flight mass spectrometry (GC TOF/MS).
PubMed:Polishing the craft of genetic diversity creation in directed evolution.
PubMed:Characterization of nucleobases and nucleosides in the fruit of Alpinia oxyphylla collected from different cultivation regions.
PubMed:In vitro and in vivo evaluation of lipofufol, a new triple stealth liposomal formulation of modulated 5-fu: impact on efficacy and toxicity.
PubMed:Nucleoterpenes of thymidine and 2'-deoxyinosine: synthons for a biomimetic lipophilization of oligonucleotides.
PubMed:Novel oxidatively activated agents modify DNA and are enhanced by ercc1 silencing.
PubMed:Construction of microbial platform for an energy-requiring bioprocess: practical 2'-deoxyribonucleoside production involving a C-C coupling reaction with high energy substrates.
PubMed:A simple and reproducible method for directed evolution: combination of random mutation with dITP and DNA fragmentation with endonuclease V.
PubMed:Simultaneous determination nucleosides in marine organisms using ultrasound-assisted extraction followed by hydrophilic interaction liquid chromatography-electrospray ionization time-of-flight mass spectrometry.
PubMed:Identification and quantification of nucleosides and nucleobases in Geosaurus and Leech by hydrophilic-interaction chromatography.
PubMed:Structure and activity of the Saccharomyces cerevisiae dUTP pyrophosphatase DUT1, an essential housekeeping enzyme.
PubMed:Identification and characterization of 2'-deoxyadenosine adducts formed by isoprene monoepoxides in vitro.
PubMed:No shot in the dark: myxozoans chemically detect fresh fish.
PubMed:Electrochemical genotyping and detection of single-nucleotide polymorphisms based on junction-probe containing 2'-deoxyinosine.
PubMed:Hybridization-sensitive fluorescent DNA probe with self-avoidance ability.
PubMed:NUDT16 and ITPA play a dual protective role in maintaining chromosome stability and cell growth by eliminating dIDP/IDP and dITP/ITP from nucleotide pools in mammals.
PubMed:Generation of 2'-deoxyadenosine N6-aminyl radicals from the photolysis of phenylhydrazone derivatives.
PubMed:Conservation of structure and activity in Plasmodium purine nucleoside phosphorylases.
PubMed:Development of a real-time reverse-transcription PCR for the detection and simultaneous pathotyping of Newcastle disease virus isolates using a novel probe.
PubMed:O6-(benzotriazol-1-yl)inosine derivatives for C6 modification of purine nucleosides.
PubMed:Antithetical effects of corticosterone and dibutyryl cAMP on adenosine deaminase in the gastrointestinal tract of chicken during postnatal development.
PubMed:The sequence dependence of human nucleotide excision repair efficiencies of benzo[a]pyrene-derived DNA lesions: insights into the structural factors that favor dual incisions.
PubMed:Separation and identification of purine nucleosides in the urine of patients with malignant cancer by reverse phase liquid chromatography/electrospray tandem mass spectrometry.
PubMed:Synthesis of N(6) ,N(6)-Dialkyl Adenine Nucleosides With In Situ Formed Hexaalkylphosphorus Triamides.
PubMed:Formation of diazoate intermediate upon nitrous acid and nitric oxide treatment of 2'-deoxyadenosine.
PubMed:Differential nucleotide excision repair susceptibility of bulky DNA adducts in different sequence contexts: hierarchies of recognition signals.
PubMed:Azide-alkyne "click" reaction performed on oligonucleotides with the universal nucleoside 7-octadiynyl-7-deaza-2'-deoxyinosine.
PubMed:Synthesis of oligonucleotide conjugated pyrrolepolyamide- and pyrrole-imidazole polyamide-2'-deoxyguanosine hybrids as novel gene expression control compounds.
PubMed:Self-Avoiding Molecular Recognition Systems (SAMRS).
PubMed:Quantification of DNA damage products resulting from deamination, oxidation and reaction with products of lipid peroxidation by liquid chromatography isotope dilution tandem mass spectrometry.
PubMed:7-Deaza-2'-deoxyinosine: a nucleoside showing ambiguous base-pairing properties against the four canonical DNA constituents.
PubMed:The fate of C5' radicals of purine nucleosides under oxidative conditions.
PubMed:Synthesis of N2-substituted deoxyguanosine nucleosides from 2-fluoro-6-O-(trimethylsilylethyl)-2'-deoxyinosine.
PubMed:A study on the inhibition of adenosine deaminase.
PubMed:Miscoding properties of 2'-deoxyinosine, a nitric oxide-derived DNA Adduct, during translesion synthesis catalyzed by human DNA polymerases.
PubMed:Synthesis and characterization of DNA containing an N1-2'-deoxyinosine-ethyl-N3-thymidine interstrand cross-link: a structural mimic of the cross-link formed by 1,3-bis-(2-chloroethyl)-1-nitrosourea.
PubMed:Rates of spontaneous disintegration of DNA and the rate enhancements produced by DNA glycosylases and deaminases.
PubMed:Anopheles gambiae purine nucleoside phosphorylase: catalysis, structure, and inhibition.
PubMed:Palladium-catalyzed synthesis of nucleoside adducts from bay- and fjord-region diol epoxides.
PubMed:Quantitative gas chromatography mass spectrometric analysis of 2'-deoxyinosine in tissue DNA.
PubMed:Lipid peroxidation dominates the chemistry of DNA adduct formation in a mouse model of inflammation.
PubMed:O6-(benzotriazol-1-yl)inosine derivatives: easily synthesized, reactive nucleosides.
PubMed:Highly diastereoselective synthesis of nucleoside adducts from the carcinogenic benzo[a]pyrene diol epoxide and a computational analysis.
PubMed:An activity-dependent assay for ricin and related RNA N-glycosidases based on electrochemiluminescence.
PubMed:Chemical radiation studies of 8-bromo-2'-deoxyinosine and 8-bromoinosine in aqueous solutions.
PubMed:Calcium-stimulated guanosine--inosine nucleosidase from yellow lupin (Lupinus luteus).
PubMed:One-pot microbial synthesis of 2'-deoxyribonucleoside from glucose, acetaldehyde, and a nucleobase.
PubMed:Potential artifacts in the measurement of DNA deamination.
PubMed:Chlamydial DNA polymerase I can bypass lesions in vitro.
PubMed:Synthesis of oligodeoxynucleotides containing a single 6alpha- or 6beta-diastereoisomer of N2-(estradiol-6-yl)-2'-deoxyguanosine.
PubMed:Relatively small increases in the steady-state levels of nucleobase deamination products in DNA from human TK6 cells exposed to toxic levels of nitric oxide.
PubMed:A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives.
PubMed:Biochemical retrosynthesis of 2'-deoxyribonucleosides from glucose, acetaldehyde, and a nucleobase.
PubMed:Development of enzymatic probes of oxidative and nitrosative DNA damage caused by reactive nitrogen species.
PubMed:Sequence-specific DNA interstrand cross-linking by an aziridinomitosene in the absence of exogenous reductant.
PubMed:Development of stealth liposome formulation of 2'-deoxyinosine as 5-fluorouracil modulator: in vitro and in vivo study.
PubMed:Synthesis and reactions of 2-chloro- and 2-tosyloxy-2'-deoxyinosine derivatives.
PubMed:Dual roles of glycosyl torsion angle conformation and stereochemical configuration in butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adducts: a structural perspective.
PubMed:Identification of a subversive substrate of Trichomonas vaginalis purine nucleoside phosphorylase and the crystal structure of the enzyme-substrate complex.
PubMed:Post-synthetic and site-specific modification of endocyclic nitrogen atoms of purines in DNA and its potential for biological and structural studies.
PubMed:The effect of the 2-amino group of 7,8-dihydro-8-oxo-2'-deoxyguanosine on translesion synthesis and duplex stability.
PubMed:Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence.
PubMed:Thermal stability of triple helical DNAs containing 2'-deoxyinosine and 2'-deoxyxanthosine.
PubMed:[Inhibition of adenosine deaminase activity by drugs influencing the cardiovascular system].
PubMed:SNAr iodination of 6-chloropurine nucleosides: aromatic Finkelstein reactions at temperatures below -40 degrees C.
PubMed:A novel synthesis of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine.
PubMed:Convenient synthesis of oligodeoxynucleotides containing 2'-deoxy-6-thioinosine.
PubMed:Absence of 2'-deoxyoxanosine and presence of abasic sites in DNA exposed to nitric oxide at controlled physiological concentrations.
PubMed:Duplex and triplex formation of oligodeoxyribonucleotides containing nucleobase-intercalater conjugates.
PubMed:Factors that contribute to efficient catalytic activity of a small Ca2+-dependent deoxyribozyme in relation to its RNA cleavage function.
PubMed:Combination of thymidine phosphorylase gene transfer and deoxyinosine treatment greatly enhances 5-fluorouracil antitumor activity in vitro and in vivo.
PubMed:Identification of the dITP- and XTP-hydrolyzing protein from Escherichia coli.
PubMed:Incorporation of oxidatively modified 2'-deoxynucleotide triphosphates by HIV-1 RT on RNA and DNA templates.
PubMed:2-aza-2'-deoxyadenosine: synthesis, base-pairing selectivity, and stacking properties of oligonucleotides.
PubMed:Hoogsteen-based parallel-stranded duplexes of DNA. Effect of 8-amino-purine derivatives.
PubMed:Preparation of oligodeoxynucleotides containing a diastereoisomer of alpha-(N(2)-2'-deoxyguanosinyl)tamoxifen by phosphoramidite chemical synthesis.
PubMed:Effects of nucleotide analogues on Euplotes aediculatus telomerase processivity: evidence for product-assisted translocation.
PubMed:Palladium catalysis for the synthesis of hydrophobic C-6 and C-2 aryl 2'-deoxynucleosides. Comparison of C-C versus C-N bond formation as well as C-6 versus C-2 reactivity.
PubMed:Synthesis and characterization of oligodeoxynucleotides containing an N1 beta-hydroxyalkyl adduct of 2'-deoxyinosine.
PubMed:The effect of amino groups on the stability of DNA duplexes and triplexes based on purines derived from inosine.
PubMed:Synthesis and characterization of nucleosides and oligonucleotides bearing adducts of butadiene epoxides on adenine n(6) and guanine n(2).
PubMed:Fluorescence properties and base pair stability of oligonucleotides containing 8-aza-7-deaza-2'-deoxyisoinosine or 2'-deoxyisoinosine.
PubMed:Inosine and 2'-deoxyinosine and their synthetic analogues: lipophilicity in the relation to their retention in reversed-phase liquid chromatography and the stability characteristics.
PubMed:Mild and efficient functionalization at C6 of purine 2'-deoxynucleosides and ribonucleosides.
PubMed:A one-pot preparation of 1-benzyl-2'-deoxyinosine from ionized 2'-deoxyinosine.
PubMed:Improved cycle sequencing of GC-rich templates by a combination of nucleotide analogs.
PubMed:Rapid and sensitive genotyping of dopamine D4 receptor tandem repeats by automated ultrathin-layer gel electrophoresis.
PubMed:Synthesis of nucleosides and oligonucleotides containing adducts of acrolein and vinyl chloride.
PubMed:Monitoring of the intracellular activation of 5-fluorouracil to deoxyribonucleotides in HT29 human colon cell line: application to modulation of metabolism and cytotoxicity study.
PubMed:Synthesis and properties of oligodeoxynucleotides containing a C-2 polyamine-bearing deoxyguanosine residue as artificial ribonuclease.
PubMed:Enhanced antitumor activity of 5-fluorouracil in combination with 2'-deoxyinosine in human colorectal cell lines and human colon tumor xenografts.
PubMed:Nucleoside analogue substitutions in the trinucleotide DNA template recognition sequence 3'-(CTG)-5' and their effects on the activity of bacteriophage T7 primase.
PubMed:Inosine and N1-methylinosine within a synthetic oligomer mimicking the anticodon loop of human tRNA(Ala) are major epitopes for anti-PL-12 myositis autoantibodies.
PubMed:Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2'-deoxyinosine: a new chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine.
PubMed:Studies on the synthesis of oligonucleotides containing photoreactive nucleosides: 2-azido-2'-deoxyinosine and 8-azido-2'-deoxyadenosine.
PubMed:Deoxyadenosine metabolism in a human colon-carcinoma cell line (LoVo) in relation to its cytotoxic effect in combination with deoxycoformycin.
PubMed:Selective amplification of RNA utilizing the nucleotide analog dITP and Thermus thermophilus DNA polymerase.
PubMed:Enzyme-substrate complexes of adenosine and cytidine deaminases: absence of accumulation of water adducts.
PubMed:Improved strategies for postoligomerization synthesis of oligodeoxynucleotides bearing structurally defined adducts at the N2 position of deoxyguanosine.
PubMed:Synthesis of N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate: comparison by 32P-postlabeling with the DNA adduct formed in HL-60 cells treated with hydroquinone.
PubMed:Reduced activity of anabolizing enzymes in 5-fluorouracil-resistant human stomach cancer cells.
PubMed:The phosphotransferase activity of cytosolic 5'-nucleotidase; a purine analog phosphorylating enzyme.
PubMed:Random mutagenesis by using mixtures of dNTP and dITP in PCR.
PubMed:Cold-sensitive conditional mutations in Era, an essential Escherichia coli GTPase, isolated by localized random polymerase chain reaction mutagenesis.
PubMed:Anti-inflammatory and anti-osteoporotic activities of base-boronated nucleosides and phosphate-boronated nucleotides in rodents.
PubMed:An invariant asparagine in the POU-specific homeodomain regulates the specificity of the Oct-2 POU motif.
PubMed:Substrate specificity of Fpg protein. Recognition and cleavage of oxidatively damaged DNA.
PubMed:Potentiation of the antitumor activity of 5-fluorouracil in colon carcinoma cells by the combination of interferon and deoxyribonucleosides results from complementary effects on thymidine phosphorylase.
PubMed:Bipartite DNA recognition by the human Oct-2 POU domain: POUs-specific phosphate contacts are analogous to those of bacteriophage lambda repressor.
PubMed:Detailed study of sequence-specific DNA cleavage of triplex-forming oligonucleotides linked to 1,10-phenanthroline.
PubMed:Gel compressions and artifact banding can be resolved in the same DNA sequence reaction.
PubMed:Substrate specificity of mitochondrial 2'-deoxyguanosine kinase. Efficient phosphorylation of 2-chlorodeoxyadenosine.
PubMed:Incorporation of dITP or 7-deaza dGTP during PCR improves sequencing of the product.
PubMed:Mechanisms of quenching of the fluorescence of a benzo[a]pyrene tetraol metabolite model compound by 2'-deoxynucleosides.
PubMed:[Hydrolysis of 5'-phosphonates and nucleoside phosphates by phosphatases of various origin and human and calf serum].
PubMed:On the validity of continuous spectrophotometric assays for adenosine deaminase activity: a critical reappraisal.
PubMed:Purification and properties of purine nucleoside phosphorylase from Brevibacterium acetylicum ATCC 954.
PubMed:Synthesis and enzymatic polymerisation of 5-amino-1-(2'-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide-5'- triphosphate.
PubMed:Enhanced antibody response in the presence of partial adenosine deaminase inhibition.
PubMed:Early postimplantation embryolethality in mice following in utero inhibition of adenosine deaminase with 2'-deoxycoformycin.
PubMed:Purification and properties of inosine-guanosine phosphorylase from Escherichia coli K-12.
PubMed:Not as simple as ABC.
PubMed:Synthesis and properties of oligonucleotides containing 2'-deoxynebularine and 2'-deoxyxanthosine.
PubMed:Phosphoramidites of base-modified 2'-deoxyinosine isosteres and solid-phase synthesis of d(GCI*CGC) oligomers containing an ambiguous base.
PubMed:Analytical studies of 'mixed sequence' oligodeoxyribonucleotides synthesized by competitive coupling of either methyl- or beta-cyanoethyl-N,N-diisopropylamino phosphoramidite reagents, including 2'-deoxyinosine.
PubMed:Direct alkylation of calf thymus DNA by acrylonitrile. Isolation of cyanoethyl adducts of guanine and thymine and carboxyethyl adducts of adenine and cytosine.
PubMed:Nucleotidase activities of human peripheral lymphocytes.
PubMed:In vitro alkylation of calf thymus DNA by acrylonitrile. Isolation of cyanoethyl-adducts of guanine and thymine and carboxyethyl-adducts of adenine and cytosine.
PubMed:Nucleoside hydrolases from Trypanosoma cruzi.
PubMed:The influence of ribose 5-phosphate availability on purine synthesis of cultured human lymphoblasts and mitogen-stimulated lymphocytes.
PubMed:A new and facile synthesis of purine 2'-amino-2'-deoxyribosides by a combination of chemical and enzymatic reactions.
PubMed:Inosine, an endogenous ligand of the brain benzodiazepine receptor, antagonizes pentylenetetrazole-evoked seizures.
PubMed:Interaction of metal ions with nucleic acids. Interaction of copper(II) with inosine and its derivatives.
PubMed:Polynucleotides. XLV Synthesis and properties of poly(2'-azido-2'-deoxyinosinic acid).
PubMed:2' Derivatives of guanosine and inosine cyclic 3',5'-phosphates. Synthesis, enzymic activity, and the effect of 8-substituents.
PubMed:Use of Escherichia coli mutants to evaluate purines, purine nucleosides, and analogues.
PubMed:Isotopic studies on 2'-deoxyinosine-8-C14 formation from inosine-8-C14 by washed cell suspension of vitamin B12-requiring strain of Lactobacillus leichmannii.
 
Notes:
Isol. from Phaseolus vulgaris (kidney bean)
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