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M2389

Sigma-Aldrich

N6-Methyl-2′-deoxyadenosine

Sinónimos:

6mdA, N6-Me-dAdo, m6dA

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About This Item

Fórmula empírica (notación de Hill):
C11H15N5O3
Número de CAS:
2002-35-9
Peso molecular:
265.27
MDL number:
MFCD00055999
UNSPSC Code:
41106305
PubChem Substance ID:
24896727
NACRES:
NA.51

assay

≥98% (TLC)

Quality Level

200

form

powder

solubility

acetic acid: 49.00-51.00 mg/mL, clear, colorless

storage temp.

−20°C

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000251260
0000226801
059M4165V
13180321
057M4031V

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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)
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
C Léon et al.
Circulation, 103(5), 718-723 (2001-02-07)
ADP plays a key role in hemostasis, acting through 2 platelet receptors: the P2Y(1) receptor and an unidentified P2 receptor, called P2cyc, coupled to adenylyl cyclase inhibition, which is the target of the antiplatelet drug clopidogrel. We showed that 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
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
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