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1867-73-8,MFCD00005739
Catalog No.:AA007S3L

1867-73-8 | N6-Methyladenosine

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1mg
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100mg
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250mg
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$9.00   $7.00
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1g
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10g
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25g
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA007S3L
Chemical Name:
N6-Methyladenosine
CAS Number:
1867-73-8
Molecular Formula:
C11H15N5O4
Molecular Weight:
281.2679
MDL Number:
MFCD00005739
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NC
Properties
Computed Properties
 
Complexity:
349  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
XLogP3:
-0.4  

Upstream Synthesis Route

[1]Heterocycles,1982,vol.17,p.117-123

[1]HelveticaChimicaActa,1994,vol.77,#5,p.1267-1280

Downstream Synthesis Route

[1]TetrahedronLetters,1975,p.2779-2782

[1]JournalofgeneralchemistryoftheUSSR,1973,vol.43,p.398-402    ZhurnalObshcheiKhimii,1973,vol.43,p.400-405

[1]JournalofOrganicChemistry,1988,vol.53,p.1887-1894

[1]ChemicalandPharmaceuticalBulletin,1990,vol.38,p.1886-1891

[1]JournaloftheAmericanChemicalSociety,1980,vol.102,p.770-774

Literature

Title: N(6)-methyladenosine mediates the cellular proliferation and apoptosis via microRNAs in arsenite-transformed cells.

Journal: Toxicology letters 20180801

Title: m(6)A modulates haematopoietic stem and progenitor cell specification.

Journal: Nature 20170914

Title: MicroRNA-145 Modulates N(6)-Methyladenosine Levels by Targeting the 3'-Untranslated mRNA Region of the N(6)-Methyladenosine Binding YTH Domain Family 2 Protein.

Journal: The Journal of biological chemistry 20170303

Title: Topology of the human and mouse m6A RNA methylomes revealed by m6A-seq.

Journal: Nature 20120429

Title: Control of substrate specificity by a single active site residue of the KsgA methyltransferase.

Journal: Biochemistry 20120110

Title: N6-methyladenosine in nuclear RNA is a major substrate of the obesity-associated FTO.

Journal: Nature chemical biology 20111201

Title: The state-of-the-art determination of urinary nucleosides using chromatographic techniques 'hyphenated' with advanced bioinformatic methods.

Journal: Analytical and bioanalytical chemistry 20111001

Title: Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.

Journal: Journal of medicinal chemistry 20110825

Title: Use of a QM/MM-based FEP method to evaluate the anomalous hydration behavior of simple alkyl amines and amides: application to the design of FBPase inhibitors for the treatment of type-2 diabetes.

Journal: Journal of the American Chemical Society 20110601

Title: Site-directed mutants of 16S rRNA reveal important RNA domains for KsgA function and 30S subunit assembly.

Journal: Biochemistry 20110208

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

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: The yfiC gene of E. coli encodes an adenine-N6 methyltransferase that specifically modifies A37 of tRNA1Val(cmo5UAC).

Journal: RNA (New York, N.Y.) 20090601

Title: Anticodon domain modifications contribute order to tRNA for ribosome-mediated codon binding.

Journal: Biochemistry 20080610

Title: MTA is an Arabidopsis messenger RNA adenosine methylase and interacts with a homolog of a sex-specific splicing factor.

Journal: The Plant cell 20080501

Title: Modified nucleosides: an accurate tumour marker for clinical diagnosis of cancer, early detection and therapy control.

Journal: British journal of cancer 20060605

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Antitumor activity of C-methyl-beta-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors.

Journal: Journal of medicinal chemistry 20050728

Title: (N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20050324

Title: Synthesis of oligoribonucleotides containing N6-alkyladenosine and 2-methylthio-N6-alkyladenosine.

Journal: Current protocols in nucleic acid chemistry 20040901

Title: Substrate analogues for an RNA-editing adenosine deaminase: mechanistic investigation and inhibitor design.

Journal: Journal of the American Chemical Society 20030910

Title: Characterization of the cAMP binding site of purified S-adenosyl-homocysteine hydrolase from bovine kidney.

Journal: Biochemical pharmacology 20021015

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Differentiation-dependent repression of c-myc, B22, COX II and COX IV genes in murine erythroleukemia (MEL) cells.

Journal: Biochemical pharmacology 20020301

Title: Chondrocytes respond to adenosine via A(2)receptors and activity is potentiated by an adenosine deaminase inhibitor and a phosphodiesterase inhibitor.

Journal: Osteoarthritis and cartilage 20020101

Title: Transcriptional activation of prion protein gene in growth-arrested and differentiated mouse erythroleukemia and human neoplastic cells.

Journal: Experimental cell research 20010401

Title: Cloning, sequencing and expression of a cDNA encoding the mouse L35a ribosomal protein during differentiation of murine erythroleukemia (MEL) cells.

Journal: Cell biology international 20010101

Title: Ribosome structure: localization of N6,N6-dimethyladenosine by electron microscopy of a ribosome-antibody complex.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19770401

Title: Wang X, et al. N6-methyladenosine-dependent regulation of messenger RNA stability. Nature. 2014 Jan 2;505(7481):117-20.

Title: Li Y, et al. Genome-wide detection of high abundance N6-methyladenosine sites by microarray. RNA. 2015 Aug;21(8):1511-8.

Title: Dang W, et al. N6-Methyladenosine and Viral Infection. Front Microbiol. 2019 Mar 5;10:417.

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