M2389

N⁶-Methyl-2′-deoxyadenosine

Name: N<SUP>6</SUP>-Methyl-2′-deoxyadenosine
Brand: SIGMA
Price: 384 USD
Availability: InStock

≥98% (TLC), powder

Synonym(s):

6mdA, N⁶-Me-dAdo, m⁶dA

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25 MG

$384.00

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₅N₅O₃

CAS Number:

2002-35-9

Molecular Weight:

265.27

MDL number:

MFCD00055999

UNSPSC Code:

41106305

PubChem Substance ID:

24896727

NACRES:

NA.51

Key Documents

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Product Name

N⁶-Methyl-2′-deoxyadenosine,

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

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Show Differences

1 of 4

This Item	D1771	D6000	M2780
Sigma-Aldrich M2389 N⁶-Methyl-2′-deoxyadenosine	Sigma-Aldrich D1771 5′-Deoxyadenosine	Sigma-Aldrich D6000 2′-Deoxyadenosine 5′-diphosphate sodium salt	Sigma-Aldrich M2780 N⁶-Methyladenosine 5′-monophosphate sodium salt
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
assay ≥98% (TLC)	assay ≥98% (TLC)	assay ≥95% (HPLC)	assay ≥97% (HPLC)
form powder	form powder	form powder	form -
solubility acetic acid: 49.00-51.00 mg/mL, clear, colorless	solubility hot water: 19.60-20.40 mg/mL, clear, colorless	solubility -	solubility -
storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C	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.[1] It has also been used to study its potential in promoting the proliferation oferythroid progenitor cells.[2]

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.[3] 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.[4] It is involved in the regulation of gene transcription, DNA repair, and replication in prokaryotes and protists.[5] N⁶-Me-dAdo complemented with gene bodies might induce gene expression in human cells.[4]

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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Certificates of Analysis (COA)

Lot/Batch Number

0000428252

0000420496

0000421222

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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)

The DNA modification N6-methyl-2'-deoxyadenosine (m6dA) drives activity-induced gene expression and is required for fear extinction.

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

Chronic fructose renders pancreatic β-cells hyper-responsive to glucose-stimulated insulin secretion through extracellular ATP signaling.

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

Key role of the P2Y(1) receptor in tissue factor-induced thrombin-dependent acute thromboembolism: studies in P2Y(1)-knockout mice and mice treated with a P2Y(1) antagonist.

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

A complementary role for tetraspanin superfamily member TSSC6 and ADP purinergic P2Y

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

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N⁶-Methyl-2′-deoxyadenosine