2002-35-9

Basic information

• Product Name: N6-METHYL-2'-DEOXY-ADENOSINE
• Synonyms: N6-METHYL-2'-DEOXY-ADENOSINE;2'-Deoxy-N6-methyl-D-adenosine;2''-Deoxy-N6-methyladenosine;(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolan-3-ol;(2R,3S,5R)-5-[6-(methylamino)purin-9-yl]-2-methylol-tetrahydrofuran-3-ol;N6-Me-dA;N6-Methyl-2'-deoxyadenosine;2'-Deoxy-N6-Methyladenosine
• CAS NO: 2002-35-9
• Molecular Formula: C₁₁H₁₅N₅O₃
• Molecular Weight: 265.27
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 2002-35-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 603.6 °C at 760 mmHg
• Flash Point: 318.8 °C
• Appearance: White to Off-white/Powder
• Density: 1.72 g/cm³
• Vapor Pressure: 2.03E-15mmHg at 25°C
• Refractive Index: 1.78
• Storage Temp.: −20°C
• PKA: 13.80±0.60(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: N6-METHYL-2'-DEOXY-ADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N6-METHYL-2'-DEOXY-ADENOSINE(2002-35-9)
• EPA Substance Registry System: N6-METHYL-2'-DEOXY-ADENOSINE(2002-35-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2002-35-9(Hazardous Substances Data)

Usage

Uses

2''-Deoxy-N-methyladenosine plays role in catalytic activity and may promote proper folding of A730 loop.

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.

InChI:InChI=1/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

Upstream product

• 17287-03-5 trimethylsulphonium hydroxide 
• 958-09-8 2'-deoxy-D-adenosine 
• 74230-06-1 trimethylselenonium hydroxyde 
• 80-48-8 methyl p-toluene sulfonate 
• 593-51-1 methylamine hydrochloride 
• 74873-17-9 N-1-methyl-2'-deoxyribofuranosiladenine iodide 
• 951-78-0 2'-deoxyuridine 
• 443-72-1 N-methyladenine 

Downstream Products

• 98056-68-9 <2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine-3'-O-yl>(methoxy)morpholinophosphine 
• 106023-62-5 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester 
• 958-09-8 2'-deoxy-D-adenosine 
• 443-72-1 N-methyladenine 
• 98056-69-0 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine 
• 402750-85-0 Phosphoric acid dibenzyl ester (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 402750-86-1 Phosphoric acid dibenzyl ester (2R,3S,5R)-2-hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Quantitative LC–MS Provides No Evidence for m6dA or m4dC in the Genome of Mouse Embryonic Stem Cells and Tissues

Until recently, it was believed that the genomes of higher organisms contain, in addition to the four canonical DNA bases, only 5-methyl-dC (m5dC) as a modified base to control epigenetic processes. In recent years, this view has changed dramatically with the discovery of 5-hydroxymethyl-dC (hmdC), 5-formyl-dC (fdC), and 5-carboxy-dC (cadC) in DNA from stem cells and brain tissue. N6-methyldeoxyadenosine (m6dA) is the most recent base reported to be present in the genome of various eukaryotic organisms. This base, together with N4-methyldeoxycytidine (m4dC), was first reported to be a component of bacterial genomes. In this work, we investigated the levels and distribution of these potentially epigenetically relevant DNA bases by using a novel ultrasensitive UHPLC–MS method. We further report quantitative data for m5dC, hmdC, fdC, and cadC, but we were unable to detect either m4dC or m6dA in DNA isolated from mouse embryonic stem cells or brain and liver tissue, which calls into question their epigenetic relevance.

Oligodeoxynucleotides containing 2′-deoxy-1-methyladenosine and Dimroth rearrangement

2′-Deoxy-1-methyladenosine was incorporated into synthetic oligonucleotides by phosphoramidite chemistry. Chloroacetyl protecting group and controlled anhydrous deprotection conditions were used to avoid Dimroth rearrangement. Hybridization studies of int

Synthesis of oligodeoxynucleotides containing 6-N-([13C]methyl)adenine and 2-N-([13C]methyl)guanine

Oligonucleotides containing 6-N-([l3C]methyl)adenine and 2-N-([13C]methyl)guanine have been prepared for NMR studies using the deprotection step to introduce the [13C]methylamine group. For this purpose, the use of 2′-deoxy-6-O-(pentafluorophenyl)inosine 1 and 2′-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)-ethyl]inosine 2 as precursors of the N-methylated nucleosides is described. Preliminary NMR characterization of the 13C-labelled oligonucleotides shows that the 13C chemical shift of the methyl group in N-methylguanine is sensitive to duplex formation, making it a useful local probe.