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About This Item
Empirical Formula (Hill Notation):
C11H15N5O3
CAS Number:
Molecular Weight:
265.27
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
MDL number:
Assay:
≥98% (TLC)
Form:
powder
Solubility:
acetic acid: 49.00-51.00 mg/mL, clear, colorless
Storage temp.:
−20°C
Product Name
N6-Methyl-2′-deoxyadenosine,
Quality Level
SMILES string
CNc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3
InChI
1S/C11H15N5O3/c1-12-10-9-11(14-4-13-10)16(5-15-9)8-2-6(18)7(3-17)19-8/h4-8,17-18H,2-3H2,1H3,(H,12,13,14)/t6-,7+,8+/m0/s1
InChI key
DYSDOYRQWBDGQQ-XLPZGREQSA-N
assay
≥98% (TLC)
form
powder
solubility
acetic acid: 49.00-51.00 mg/mL, clear, colorless
storage temp.
−20°C
Application
N6-Methyl-2′-deoxyadenosine has been used as a standard to assess the levels of modified bases in genomic DNA by the ultra-high-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UHPLC-QQQ-MS/MS) method. It has also been used to study its potential in promoting the proliferation oferythroid progenitor cells.
Biochem/physiol Actions
N6-Methyl-2′-deoxyadenosine (N6-Me-dAdo) is a precursor of N6-methyl 2′-deoxyadenosine 3′,5′-bisphosphate (N6MABP), a competitive and selective inhibitor of P2Y1 receptors. It is located at the transcription start site and plays a role in increased gene expression in Chlamydomonas reindardtii. N6-Me-dAdo augments the within transposable elements and is present at higher levels during the development of Drosophila. It is involved in the regulation of gene transcription, DNA repair, and replication in prokaryotes and protists. N6-Me-dAdo complemented with gene bodies might induce gene expression in human cells.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Determination of DNA adenine methylation in genomes of mammals and plants by liquid chromatography/mass spectrometry
Huang W, et al.
Royal Society of Chemistry Advances, 5(79), 64046-64054 (2015)
Mohammed Makkawi et al.
Thrombosis research, 161, 12-21 (2017-11-28)
Tumor-suppressing subchromosomal transferable fragment cDNA 6 (TSSC6) expression is restricted to hematopoietic organs and tissues where it plays a role in hematopoietic-cell function. The ADP purinergic receptor P2Y
Frederic Marteau et al.
Molecular pharmacology, 64(1), 104-112 (2003-06-20)
The P2Y13 receptor has recently been identified as a new P2Y receptor sharing a high sequence homology with the P2Y12 receptor as well as similar functional properties: coupling to Gi and responsiveness to ADP (Communi et al., 2001). In the
Clarissa Bartley et al.
American journal of physiology. Endocrinology and metabolism, 317(1), E25-E41 (2019-03-27)
Fructose is widely used as a sweetener in processed food and is also associated with metabolic disorders, such as obesity. However, the underlying cellular mechanisms remain unclear, in particular, regarding the pancreatic β-cell. Here, we investigated the effects of chronic
Xiang Li et al.
Nature neuroscience, 22(4), 534-544 (2019-02-20)
DNA modification is known to regulate experience-dependent gene expression. However, beyond cytosine methylation and its oxidated derivatives, very little is known about the functional importance of chemical modifications on other nucleobases in the brain. Here we report that in adult
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