98056-69-0

Basic information

• Product Name: 5'-O-(DIMETHOXYTRITYL)-N6-METHYL-2'-DEOXYADENOSINE
• Synonyms: 5'-O-(DIMETHOXYTRITYL)-N6-METHYL-2'-DEOXYADENOSINE;N6-ME-DMT-DEOXYADENOSINE;2'-Deoxy-5'-O-DMT-N6-methyladenosine;5'-O-(4,4'-DiMethoxytriphenylMethyl)-N6-Methyl-2'-deoxyadenosine;5'-O-[Bis(4-Methoxyphenyl)phenylMethyl]-2'-deoxy-N-Methyladenosine;5'-O-DMT-2'-deoxy-N-Methyl-adenosine;Adenosine, 5'-O-[bis(4-Methoxyphenyl)phenylMethyl]-2'-deoxy-N-Methyl-;2'-Deoxy-5'-O-dimethoxytrityl-N6-methyladenosine
• CAS NO: 98056-69-0
• Molecular Formula: C₃₂H₃₃N₅O₅
• Molecular Weight: 567.63
• Product Categories: Aromatics;Bases & Related Reagents;Intermediates;Nucleotides
• Mol File: 98056-69-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5'-O-(DIMETHOXYTRITYL)-N6-METHYL-2'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(DIMETHOXYTRITYL)-N6-METHYL-2'-DEOXYADENOSINE(98056-69-0)
• EPA Substance Registry System: 5'-O-(DIMETHOXYTRITYL)-N6-METHYL-2'-DEOXYADENOSINE(98056-69-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 98056-69-0(Hazardous Substances Data)

Usage

Uses

5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-N-methyladenosine is a 5’-O-(4,4'-Dimethoxytriphenylmethy) substitued derivative of the 2’-deoxy N-methyl analogue of Adenosine. It is used in the preparation of oligonucleotides containing N6-methyladenine residues in the GATC site.

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 2002-35-9 N-6-methyl-2'-deoxyribofuranosil adenine 
• 74873-17-9 N-1-methyl-2'-deoxyribofuranosiladenine iodide 

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 
• 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

Homopurine: R P-stereodefined phosphorothioate analogs of DNA with hampered Watson-Crick base pairings form Hoogsteen paired parallel duplexes with (2′-OMe)-RNAs

3′-O-(2-Thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) derivatives of 5′-O-DMT-N6-methyl-deoxyadenosine and 5′-O-DMT-N2,N2-dimethyl-O6-diphenylcarbamoyl-deoxyguanosine (OTP-NY, NY = DMT-m6dA or DMT-m,m2dGDPC) were synthesized, resolved onto pure P-diastereomers, and used in P-stereocontrolled synthesis of dinucleoside 3′,5,-phosphorothioates NXPST (NX = m6dA or m,m2dG), in which the absolute configuration of the stereogenic phosphorus atom was established enzymatically. Diastereomerically pure OTP-NY and standard OTP-N (N = DMT-dABz or DMT-dGBz,DPC) were used in the synthesis of chimeric RP-stereodefined phosphorothioate oligomers ((RP-PS)-DN(NX)A) with hampered Watson-Crick base pairings. It was found that the m6dA units slightly reduce the thermodynamic stability of antiparallel duplexes formed with RNA and (2′-OMe)-RNA matrices, whereas m,m2dG units prevent their formation. The m6dA units stabilize (by up to 4.5 °C per modified unit) the parallel duplexes formed by (RP-PS)-DN(NX)A with Hoogsteen-paired (2′-OMe)-RNA templates compared to the analogous reference duplex containing only unmodified nucleobases. In contrast, the m,m2dG units destabilize such duplexes by up to 3 °C per modified unit. Both units prevent the formation of the corresponding parallel triplexes.

Novel antagonists acting at the P2Y1 purinergic receptor: Synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques

The human P2Y1 receptor is widely distributed in many tissues and has a classical structure of a G protein-coupled receptor. Activated by adenosine-5′-diphosphate (ADP), this receptor is essential for platelet aggregation. In the present paper,

Synthesis and Properties of Phosphoramidite Derivatives of Modified Nucleosides

Protected N6-methyl-2'-deoxyadenosine (d-m6A), 2-amino-2'-deoxyadenosine (d-a2A), 2'-deoxyinosine (dI), 5-methyl-2'-deoxycytidine (d-m5C) and deoxyuridine (dU) were reacted with bis(diisopropylamino)methoxyphosphine in the presence of diisopropylammonium tetrazolide as the activating reagent to give the corresponding phosphoramidite derivatives in yields of 100, 65, 90, 78 and 65 percent respectively.The 31P-nuclear magnetic resonance spectra of the products were measured.Using these compounds, dinucleotides and trinucleotides were synthesized on a longchain alkylamine controlled pore glass (LCA-CPG) in quantitative yields.The stability of 6-methyldeoxyadenosine and N,N-diisobutyryl-2-aminodeoxyadenosine to acid was examined.When protected di- and trinucleotides (m6A-T, a2A-T, T-m6A-T, T-a2A-T) bound to the support (LCA-CPG) were treated with 3 percent trichloroacetic acid in dichloromethane, depurination was negligible within 10 min (dinucleotide) or 60 min (trinucleotide).Keywords - phosphoramidite; solid-phase synthesis; phosphite method; acid treatment; enzyme degradation