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2457-80-9,MFCD00010533
Catalog No.:AA002OIX

2457-80-9 | 5'-S-Methyl-5'-thioadenosine

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1mg
97%
in stock  
$6.00   $4.00
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50mg
95%
in stock  
$47.00   $33.00
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100mg
97%
in stock  
$52.00   $36.00
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250mg
95%
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$81.00   $57.00
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1g
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5g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002OIX
Chemical Name:
5'-S-Methyl-5'-thioadenosine
CAS Number:
2457-80-9
Molecular Formula:
C11H15N5O3S
Molecular Weight:
297.3335
MDL Number:
MFCD00010533
SMILES:
CSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
Properties
Computed Properties
 
Complexity:
352  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
-0.3  

Downstream Synthesis Route

[1]Parks;Schlenk[JournalofBiologicalChemistry,1958,vol.230,p.295,298]

[2]Mudd[JournalofBiologicalChemistry,1959,vol.234,p.87,88]

[3]Guerard,Christine;Breard,Maud;Courtois,Fabienne;Drujon,Thierry;Ploux,Olivier[BioorganicandMedicinalChemistryLetters,2004,vol.14,#7,p.1661-1664]

[1]Levene;Sobotka[JournalofBiologicalChemistry,1925,vol.65,p.551,554]Suzuki;Mori[BiochemischeZeitschrift,1925,vol.162,p.413,417]Suzukietal.[BiochemischeZeitschrift,1924,vol.154,p.278,279][NipponNogeiKagakuKaishi,1924,vol.1,p.127,128]Levene[JournalofBiologicalChemistry,1924,vol.59,p.465,469]

[2]Levene;Sobotka[JournalofBiologicalChemistry,1925,vol.65,p.551,554]Suzuki;Mori[BiochemischeZeitschrift,1925,vol.162,p.413,417]Suzukietal.[BiochemischeZeitschrift,1924,vol.154,p.278,279][NipponNogeiKagakuKaishi,1924,vol.1,p.127,128]Levene[JournalofBiologicalChemistry,1924,vol.59,p.465,469]

[1]Wnuk;Stoeckler;Robins[NucleosidesandNucleotides,1994,vol.13,#1-3,p.389-403]

[2]Kuhn;Henkel[Hoppe-Seyler'sZeitschriftfurPhysiologischeChemie,1941,vol.269,p.41,45]SATOH;MAKINO[Nature,1951,vol.167,#4241,p.238-238]Satoh[JournalofBiochemistry,1953,vol.40,p.563,567]

[3]Tyler,PeterC.;Taylor,ErikaA.;Froehlich,RichardF.G.;Schramm,VernL.[JournaloftheAmericanChemicalSociety,2007,vol.129,#21,p.6872-6879]

[4]Tyler,PeterC.;Taylor,ErikaA.;Froehlich,RichardF.G.;Schramm,VernL.[JournaloftheAmericanChemicalSociety,2007,vol.129,#21,p.6872-6879]

[5]Tyler,PeterC.;Taylor,ErikaA.;Froehlich,RichardF.G.;Schramm,VernL.[JournaloftheAmericanChemicalSociety,2007,vol.129,#21,p.6872-6879]

[6]Goble,AlissaM.;Toro,Rafael;Li,Xu;Ornelas,Argentina;Fan,Hao;Eswaramoorthy,Subramaniam;Patskovsky,Yury;Hillerich,Brandan;Seidel,Ron;Sali,Andrej;Shoichet,BrianK.;Almo,StevenC.;Swaminathan,Subramanyam;Tanner,MartinE.;Raushel,FrankM.[Biochemistry,2013,vol.52,#37,p.6525-6536]

[1]Satoh[JournalofBiochemistry,1953,vol.40,p.563,567]

[2]Weygand;Trauth[ChemischeBerichte,1951,vol.84,p.633]

[3]Baddiley[JournaloftheChemicalSociety,1951,p.1348,1351]Baddiley;Jamieson[JournaloftheChemicalSociety,1954,p.4280,4283]

[1]Robins;Wnuk;Mullah;Dalley;Yuan;Lee;Borchardt[JournalofOrganicChemistry,1994,vol.59,#3,p.544-555]

[2]CurrentPatentAssignee:PARSONSBRINCKERHOFFGROUPINC-WO2018/212980,2018,A1Locationinpatent:Paragraph00221

[3]Guillerm,Georges;Gatel,Marie[JournaloftheChemicalSociety.PerkintransactionsI,1994,#2,p.153-154]

[4]Sufrin,JaniceR.;Spiess,ArthurJ.;Kramer,DeboraL.;Libby,PaulR.;Porter,CarlW.[JournalofMedicinalChemistry,1989,vol.32,#5,p.997-1001]

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Title: Growth control of the eukaryote cell: a systems biology study in yeast.

Journal: Journal of biology 20070101

Title: A novel approach for determining cancer genomic breakpoints in the presence of normal DNA.

Journal: PloS one 20070101

Title: Metabolic signature of breast cancer cell line MCF-7: profiling of modified nucleosides via LC-IT MS coupling.

Journal: BMC biochemistry 20070101

Title: Expression of cancer-associated molecules in malignant mesothelioma.

Journal: Biomarker insights 20070101

Title: Trypanothione reductase: a viable chemotherapeutic target for antitrypanosomal and antileishmanial drug design.

Journal: Drug target insights 20070101

Title: The complete genome sequence and comparative genome analysis of the high pathogenicity Yersinia enterocolitica strain 8081.

Journal: PLoS genetics 20061201

Title: The effect of a novel transition state inhibitor of methylthioadenosine phosphorylase on pemetrexed activity.

Journal: Molecular cancer therapeutics 20061001

Title: The methionine salvage pathway compound 4-methylthio-2-oxobutanate causes apoptosis independent of down-regulation of ornithine decarboxylase.

Journal: Biochemical pharmacology 20060928

Title: Methylthioadenosine reverses brain autoimmune disease.

Journal: Annals of neurology 20060901

Title: Toxoplasma gondii purine nucleoside phosphorylase biochemical characterization, inhibitor profiles, and comparison with the Plasmodium falciparum ortholog.

Journal: The Journal of biological chemistry 20060901

Title: The prognostic significance of CDKN2A, CDKN2B and MTAP inactivation in B-lineage acute lymphoblastic leukemia of childhood. Results of the EORTC studies 58881 and 58951.

Journal: Haematologica 20060701

Title: Histone H3 lysine 4 dimethylation signals the transcriptional competence of the adiponectin promoter in preadipocytes.

Journal: The Journal of biological chemistry 20060623

Title: Lack of methylthioadenosine phosphorylase expression in mantle cell lymphoma is associated with shorter survival: implications for a potential targeted therapy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060615

Title: Differential regulation of the JNK/AP-1 pathway by S-adenosylmethionine and methylthioadenosine in primary rat hepatocytes versus HuH7 hepatoma cells.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20060601

Title: Synthesis of a potent 5'-methylthioadenosine/S-adenosylhomocysteine (MTAN) inhibitor.

Journal: Bioorganic & medicinal chemistry letters 20060515

Title: Methylthioadenosine and polyamine biosynthesis in a Saccharomyces cerevisiae meu1delta mutant.

Journal: Biochemical and biophysical research communications 20060428

Title: Development of high-throughput spermidine synthase activity assay using homogeneous time-resolved fluorescence.

Journal: Analytical biochemistry 20060415

Title: Methylthioadenosine phosphorylase gene deletions are frequently detected by fluorescence in situ hybridization in conventional chondrosarcomas.

Journal: Cancer genetics and cytogenetics 20060415

Title: Impact of quorum sensing on fitness of Pseudomonas aeruginosa.

Journal: International journal of medical microbiology : IJMM 20060401

Title: Tissue microarray analysis of methylthioadenosine phosphorylase protein expression in melanocytic skin tumors.

Journal: Archives of dermatology 20060401

Title: Fine-mapping loss of gene architecture at the CDKN2B (p15INK4b), CDKN2A (p14ARF, p16INK4a), and MTAP genes in head and neck squamous cell carcinoma.

Journal: Archives of otolaryngology--head & neck surgery 20060401

Title: The crystal structure of 5'-deoxy-5'-methylthioadenosine phosphorylase II from Sulfolobus solfataricus, a thermophilic enzyme stabilized by intramolecular disulfide bonds.

Journal: Journal of molecular biology 20060317

Title: EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine.

Journal: Blood 20060201

Title: Circadian pharmacology of L-alanosine (SDX-102) in mice.

Journal: Molecular cancer therapeutics 20060201

Title: Promoter-hypermethylation is causing functional relevant downregulation of methylthioadenosine phosphorylase (MTAP) expression in hepatocellular carcinoma.

Journal: Carcinogenesis 20060101

Title: S-adenosylmethionine or 5'-methylthioadenosine are unable to prevent fumonisin B1 hepatotoxicity in mice despite increased oxidation in liver.

Journal: Journal of applied toxicology : JAT 20060101

Title: Comparative protein modeling of spermidine synthase from Plasmodium falciparum: A potential target for anti-malarial drug therapy.

Journal: Bioinformation 20060101

Title: Homozygous deletions of methylthioadenosine phosphorylase in human biliary tract cancers.

Journal: Molecular cancer therapeutics 20051201

Title: Concordant loss of MTAP and p16/CDKN2A expression in gastroesophageal carcinogenesis: evidence of homozygous deletion in esophageal noninvasive precursor lesions and therapeutic implications.

Journal: The American journal of surgical pathology 20051101

Title: S-adenosylmethionine blocks collagen I production by preventing transforming growth factor-beta induction of the COL1A2 promoter.

Journal: The Journal of biological chemistry 20050902

Title: Second generation transition state analogue inhibitors of human 5'-methylthioadenosine phosphorylase.

Journal: Journal of medicinal chemistry 20050714

Title: Concordant loss of MTAP and p16/CDKN2A expression in pancreatic intraepithelial neoplasia: evidence of homozygous deletion in a noninvasive precursor lesion.

Journal: Modern pathology : an official journal of the United States and Canadian Academy of Pathology, Inc 20050701

Title: The expression of endothelial nitric-oxide synthase is controlled by a cell-specific histone code.

Journal: The Journal of biological chemistry 20050701

Title: Implications of P16/CDKN2A deletion in pleural mesotheliomas.

Journal: Lung cancer (Amsterdam, Netherlands) 20050701

Title: Design, synthesis, and biological evaluation of novel human 5'-deoxy-5'-methylthioadenosine phosphorylase (MTAP) substrates.

Journal: Bioorganic & medicinal chemistry letters 20050602

Title: Structural rationale for the affinity of pico- and femtomolar transition state analogues of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase.

Journal: The Journal of biological chemistry 20050506

Title: Femtomolar transition state analogue inhibitors of 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase from Escherichia coli.

Journal: The Journal of biological chemistry 20050506

Title: A nucleosidase required for in vivo function of the S-adenosyl-L-methionine radical enzyme, biotin synthase.

Journal: Chemistry & biology 20050501

Title: Regulation of human methylthioadenosine phosphorylase gene by the CBF (CCAAT binding factor)/NF-Y (nuclear factor-Y).

Journal: The Biochemical journal 20050401

Title: Methylthioadenosine phosphorylase gene is silenced by promoter hypermethylation in human lymphoma cell line DHL-9: another mechanism of enzyme deficiency.

Journal: International journal of oncology 20050401

Title: Chemical mechanism and substrate specificity of RhlI, an acylhomoserine lactone synthase from Pseudomonas aeruginosa.

Journal: Biochemistry 20050301

Title: Ewing sarcomas with p53 mutation or p16/p14ARF homozygous deletion: a highly lethal subset associated with poor chemoresponse.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050120

Title: Strong expression of methylthioadenosine phosphorylase (MTAP) in human colon carcinoma cells is regulated by TCF1/[beta]-catenin.

Journal: Laboratory investigation; a journal of technical methods and pathology 20050101

Title: Bayesian phylogenetic analysis reveals two-domain topology of S-adenosylhomocysteine hydrolase protein sequences.

Journal: Molecular phylogenetics and evolution 20050101

Title: Comparative analysis of RNA regulatory elements of amino acid metabolism genes in Actinobacteria.

Journal: BMC microbiology 20050101

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Journal: BMC structural biology 20050101

Title: Design and evaluation of 5'-modified nucleoside analogs as prodrugs for an E. coli purine nucleoside phosphorylase mutant.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: Functional analysis of methylthioribose kinase genes in plants.

Journal: Plant physiology 20041201

Title: Methylthioadenosine phosphorylase from the archaeon Pyrococcus furiosus. Mechanism of the reaction and assignment of disulfide bonds.

Journal: European journal of biochemistry 20041201

Title: Methylthioadenosine phosphorylase gene expression is impaired in human liver cirrhosis and hepatocarcinoma.

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Title: Loss of methylthioadenosine phosphorylase and elevated ornithine decarboxylase is common in pancreatic cancer.

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Title: Comprehensive analysis of the 9p21 region in neuroblastoma suggests a role for genes mapping to 9p21-23 in the biology of favourable stage 4 tumours.

Journal: British journal of cancer 20040913

Title: Crystal structure of yeast Ypr118w, a methylthioribose-1-phosphate isomerase related to regulatory eIF2B subunits.

Journal: The Journal of biological chemistry 20040827

Title: Inhibition of lipopolysaccharide-stimulated TNF-alpha promoter activity by S-adenosylmethionine and 5'-methylthioadenosine.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20040801

Title: Analogs of 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-(methylthio)pentane, an acyclic intermediate in the methionine salvage pathway: a new preparation and characterization of activity with E1 enolase/phosphatase from Klebsiella oxytoca.

Journal: Bioorganic & medicinal chemistry 20040715

Title: S-adenosylmethionine and its metabolite induce apoptosis in HepG2 cells: Role of protein phosphatase 1 and Bcl-x(S).

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Title: Delivery systems and molecular targets of mechanism-based therapies for GBM.

Journal: Expert review of neurotherapeutics 20040701

Title: Metabolic and antiproliferative consequences of activated polyamine catabolism in LNCaP prostate carcinoma cells.

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Title: [Expression and clinical significance of methylthioadenosine phosphorylase gene in patients with non-small cell lung cancer].

Journal: Zhonghua yi xue za zhi 20040602

Title: Antioxidant properties of S-adenosyl-L-methionine in Fe(2+)-initiated oxidations.

Journal: Free radical biology & medicine 20040515

Title: Novel amino acid derived natural products from the ascidian Atriolum robustum: identification and pharmacological characterization of a unique adenosine derivative.

Journal: Journal of medicinal chemistry 20040422

Title: Synthesis and evaluation of analogues of S-adenosyl-L-methionine, as inhibitors of the E. coli cyclopropane fatty acid synthase.

Journal: Bioorganic & medicinal chemistry letters 20040405

Title: 5'-methylthioadenosine modulates the inflammatory response to endotoxin in mice and in rat hepatocytes.

Journal: Hepatology (Baltimore, Md.) 20040401

Title: Pharmacology and mechanism of action of pemetrexed.

Journal: Clinical lung cancer 20040401

Title: Heparan sulfate proteoglycans function as receptors for fibroblast growth factor-2 activation of extracellular signal-regulated kinases 1 and 2.

Journal: Circulation research 20040220

Title: Picomolar transition state analogue inhibitors of human 5'-methylthioadenosine phosphorylase and X-ray structure with MT-immucillin-A.

Journal: Biochemistry 20040113

Title: Bacterial variations on the methionine salvage pathway.

Journal: BMC microbiology 20040101

Title: Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells.

Journal: Oncology research 20040101

Title: Branched-chain amino acid aminotransferase and methionine formation in Mycobacterium tuberculosis.

Journal: BMC microbiology 20040101

Title: Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites.

Journal: The Journal of biological chemistry 20031212

Title: Altered gene expression in liver from a murine model of hyperhomocysteinemia.

Journal: The Journal of biological chemistry 20030822

Title: Identification of gene expression profiles predicting tumor cell response to L-alanosine.

Journal: Biochemical pharmacology 20030815

Title: Characterization of methylthioadenosin phosphorylase (MTAP) expression in malignant melanoma.

Journal: The American journal of pathology 20030801

Title: Anaplerotic reactions in tumour proliferation and apoptosis.

Journal: Biochemical pharmacology 20030801

Title: Homozygous deletion of CDKN2A and codeletion of the methylthioadenosine phosphorylase gene in the majority of pleural mesotheliomas.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20030601

Title: CDKN2A, CDKN2B, and MTAP gene dosage permits precise characterization of mono- and bi-allelic 9p21 deletions in childhood acute lymphoblastic leukemia.

Journal: Genes, chromosomes & cancer 20030501

Title: Structure of Escherichia coli 5'-methylthioadenosine/ S-adenosylhomocysteine nucleosidase inhibitor complexes provide insight into the conformational changes required for substrate binding and catalysis.

Journal: The Journal of biological chemistry 20030307

Title: Characterisation of methionine adenosyltransferase from Mycobacterium smegmatis and M. tuberculosis.

Journal: BMC microbiology 20030101

Title: Modeling and experiment yields the structure of acireductone dioxygenase from Klebsiella pneumoniae.

Journal: Nature structural biology 20021201

Title: Methylthioadenosine phosphorylase, a gene frequently codeleted with p16(cdkN2a/ARF), acts as a tumor suppressor in a breast cancer cell line.

Journal: Cancer research 20021115

Title: Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL).

Journal: Leukemia 20020901

Title: S-adenosylmethionine conformations in solution and in protein complexes: conformational influences of the sulfonium group.

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Title: Deletion of dinucleotide repeat (Delta 14 allele) in the methylthioadenosine phosphorylase (MTAP) promoter and the allelotype of MTAP promoter in the Japanese population.

Journal: Japanese journal of cancer research : Gann 20020401

Title: Methylthioadenosine phosphorylase gene deletions are common in osteosarcoma.

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Title: S-adenosylmethionine decarboxylase from Leishmania donovani. Molecular, genetic, and biochemical characterization of null mutants and overproducers.

Journal: The Journal of biological chemistry 20020222

Title: S-adenosylmethionine and methylthioadenosine are antiapoptotic in cultured rat hepatocytes but proapoptotic in human hepatoma cells.

Journal: Hepatology (Baltimore, Md.) 20020201

Title: Protein repair methyltransferase from the hyperthermophilic archaeon Pyrococcus furiosus. Unusual methyl-accepting affinity for D-aspartyl and N-succinyl-containing peptides.

Journal: The Journal of biological chemistry 20020111

Title: Methylthioadenosine phosphorylase as target for chemoselective treatment of T-cell acute lymphoblastic leukemic cells.

Journal: Blood cells, molecules & diseases 20020101

Title: The methionine salvage pathway in Bacillus subtilis.

Journal: BMC microbiology 20020101

Title: Isolation and properties of arginase from a shade plant, ginseng (Panax ginseng C.A. Meyer) roots.

Journal: Phytochemistry 20011201

Title: Glutamate 47 in 1-aminocyclopropane-1-carboxylate synthase is a major specificity determinant.

Journal: Biochemistry 20011016

Title: Mechanistic studies of two dioxygenases in the methionine salvage pathway of Klebsiella pneumoniae.

Journal: Biochemistry 20010529

Title: Arginine methylation of STAT1 modulates IFNalpha/beta-induced transcription.

Journal: Cell 20010309

Title: 5'-Methylthioadenosine administration prevents lipid peroxidation and fibrogenesis induced in rat liver by carbon-tetrachloride intoxication.

Journal: Journal of hepatology 20010301

Title: In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense.

Journal: Biochemical pharmacology 20010215

Title: Expression, purification, crystallization and preliminary X-ray analysis of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase.

Journal: Acta crystallographica. Section D, Biological crystallography 20010101

Title: Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.

Journal: Genome biology 20010101

Title: MtnK, methylthioribose kinase, is a starvation-induced protein in Bacillus subtilis.

Journal: BMC microbiology 20010101

Title: Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts.

Journal: Biochemical pharmacology 19940302

Title: Antimicrobial and antiviral activity of xylosyl-methylthio-adenosine, a naturally occurring analogue of methylthio-adenosine from Doris verrucosa.

Journal: Experientia 19911201

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Tags:2457-80-9 Molecular Formula|2457-80-9 MDL|2457-80-9 SMILES|2457-80-9 5'-S-Methyl-5'-thioadenosine