869354-99-4

Basic information

• Product Name: 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE
• Synonyms: 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE;2-(Dimethylaminomethylidene)amino-6-methoxylamino-9-(β-D-2-deoxyribofuranosyl)purine
• CAS NO: 869354-99-4
• Molecular Formula: C₁₄H₂₁N₇O₄
• Molecular Weight: 351.36
• Mol File: 869354-99-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE(869354-99-4)
• EPA Substance Registry System: 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE(869354-99-4)

Safety Data

• Hazardous Substances Data: 869354-99-4(Hazardous Substances Data)

Usage

Description

2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE is a derivative of 6-(Methylamino)purine (M287005), a reagent for substitution of adenine nucleotide analogs containing a bicyclohexane ring system locked in the northern conformation. This unique structure enhances its potency as a receptor antagonist. Additionally, adenine methylation as an epigenetic mark has been observed in single-celled organisms and, less commonly, in mammalian cells.

Uses

Used in Pharmaceutical Industry:
2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE is used as a research compound for the development of novel therapeutic agents. Its unique structure and enhanced potency as a receptor antagonist make it a promising candidate for the treatment of various diseases, particularly those involving adenine nucleotide analogs.
Used in Epigenetic Research:
In the field of epigenetics, 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE serves as a valuable tool for studying adenine methylation. Its presence in single-celled organisms and rare occurrence in mammalian cells provide insights into the role of this epigenetic mark in cellular processes and its potential implications for human health and disease.

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 136986-34-0 2-amino-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-6-methoxyaminopurine 
• 35095-93-3 2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine 
• 68045-42-1 2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one O-methyl-oxime 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 136986-37-3 9-<2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl>-2-dimethyleneamino-6-methoxyaminopurine 3'-(2-cyanoethyl N,N-di-isopropylphosphoramidite) 
• 136986-36-2 N'-{9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine 

Relevant articles and documents

Synthesis and duplex stability of oligonucleotides containing adenine-guanine analogues

The nucleosides N6-methoxy-2'-deoxyadenosine (dZ) and 2-amino-9-(2-deoxy-β-ribofuranosyl)-6-methoxyaminopurine (dK) have been synthesised and converted into 5'-O-dimethoxytrityl 3'-(2-cyanoethyl N,N-diisopropylphosphoramidites). These monomers have been used in machine DNA synthesis to give a set of heptadecanucleotides containing up to three analogue nucleotides. The melting transitions (T(m) show that the 17-mer duplexes containing Z·T and Z·C base-pairs have closely similar stabilities, as have those containing K·T and K·C pairs. They are less stable than the corresponding fully complementary duplexes, but more stable than those containing mismatched pairs. This, in the case of dZ, is in accord with the amino-imino tautomeric ratio of ~1:4 observed for the nucleoside in methyl sulfoxide. The application of oligomers containing such 'degenerate' bases in oligonucleotide probes and primers is discussed. The nucleosides N6-methoxy-2′-deoxyadenosine (dZ) and 2-amino-9-(2-deoxy-β-ribofuranosyl)-6-methoxyaminopurine (dK) have been synthesised and converted into 5′-O-dimethoxytrityl 3′-(2-cyanoethyl N,N-diisopropylphosphoramidites). These monomers have been used in machine DNA synthesis to give a set of heptadecanucleotides containing up to three analogue nucleotides. The melting transitions (Tm) show that the 17-mer duplexes containing Z·T and Z·C base-pairs have closely similar stabilities, as have those containing K·T and K·C pairs. They are less stable than the corresponding fully complementary duplexes, but more stable than those containing mismatched pairs. This, in the case of dZ, is in accord with the amino-imino tautomeric ratio of approximately 1:4 observed for the nucleoside in methyl sulfoxide. The application of oligomers containing such 'degenerate' bases in oligonucleotide probes and primers is discussed.