2140-79-6

Basic information

• Product Name: 2'-O-Methyladenosine
• Synonyms: AMI;2'-O-Methyladdenosine;(2R,3R,4R,5R)-5-(6-AMino-9H-purin-9-yl)-2-(hydroxyMethyl)-4-Methoxytetrahydrofuran-3-ol;2'-O-METHYLADENOSINE;2'-O-Methyl-D-adenosine;5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol;2'-OMe-A;(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
• CAS NO: 2140-79-6
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.27
• EINECS: 1308068-626-2
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 2140-79-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 200-202 C
• Boiling Point: 623.759 °C at 760 mmHg
• Flash Point: 331.038 °C
• Appearance: White to Off-white/Powder
• Density: 1.843 g/cm³
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• PKA: 13.13±0.70(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 2'-O-Methyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-Methyladenosine(2140-79-6)
• EPA Substance Registry System: 2'-O-Methyladenosine(2140-79-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2140-79-6(Hazardous Substances Data)

Usage

Description

2'-O-Methyladenosine, also known as Cordysinin B, is a member of the adenosine class, where the hydroxy group at position 2' is replaced by a methoxy group. It is a fungal metabolite isolated from the mycelia of Cordyceps sinensis and serves as a nucleoside modification with antiviral properties. As an ether and a white solid, it is an analog of adenosine and a starting material for 2'-O'-methyl nucleotides, with the potential to be a metabolite of 2'-O-Me-cAMP.

Uses

Used in Pharmaceutical Industry:
2'-O-Methyladenosine is used as an adenosine analog for preparing nucleoside derivatives, which act as inhibitors of RNA-dependent RNA viral polymerase. This application is crucial in the development of antiviral drugs targeting specific viral enzymes, thereby offering potential treatments for viral infections.
Used in Biochemical Research:
As a nucleoside modification, 2'-O-Methyladenosine is utilized in biochemical research to study the effects of methyl group addition on the 2' hydroxyl of the ribose moiety of adenosine. This research can provide insights into the structure-function relationships of nucleosides and their role in various biological processes, including the development of novel therapeutic agents.

Preparation

preparation of 2′-O-MethyladenosineMethylation of adenosine with methyl iodide in anhydrous alkaline mediumAdenosine is treated with CH3I in an anhydrous alkaline medium at 0°C for 4 h. The major products of this reaction are monomethylated adenosine at either the 2′-O or 3′-O position (total of 64%) and the side products are dimethylated adenosine (2′,3′-O-dimethyladenosi, 21%, and N6-2′-O-dimethyladenosine, 11%). The ratio of 2′-O- and 3′-O-methyladenosine has been found to be 8 to 1. Therefore, this reaction preferentially favors the synthesis of 2′-O-methyladenosine. The monomethylated adenosine is isolated from reaction mixture by a silica gel column chromatography. Then the pure 2′-O-methyladenosine can be separated by crystallization in ethanol from the mixture of 2′-O and 3′-O-methylated isomers. The overall yield of 2′-O-methyladenosine is 42%.https://doi.org/10.1016/0304-4165(80)90276-7

Biological Activity

2'-O-Methyladenosine, a methylated adenine residue is found in urine of normals as well as in urine of adenosine deaminase (ADA) deficient patients. 2'-O-Methyladenosine exhibits unique hypotensive activities.

Upstream product

• 58-61-7 adenosine 
• 74-88-4 methyl iodide 
• 80-48-8 methyl p-toluene sulfonate 
• 57817-83-1 N⁶,O^2'-methyladenosine 
• 684-93-5 1-methyl-1-nitrosourea 
• 647834-80-8 O-levulinyl acetonoxime 
• 10300-22-8 3'-O-methyladenosine 
• 186581-53-3 diazomethane 
• 110-71-4 1,2-dimethoxyethane 
• 244184-56-3 3',5'-di-O-acetyl-2'-O-methyl-6-chloro-2-aminopurine riboside 
• 194034-59-8 2-amino-6-chloro-9-[2'-O-methyl-β-D-ribofuranosyl]purine 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 17287-03-5 trimethylsulphonium hydroxide 
• 194034-61-2 6-chloro-9-[3',5'-di-O-acetyl-2'-O-methyl-β-D-ribofuranosyl] purine 

Downstream Products

• 24121-00-4 2'-O-Methyladenosin 5'-phosphat 
• 28990-73-0 9-(2-O-methyl-5-O-trityl-β-D-ribofluranosyl)adenine 
• 296802-65-8 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propargylinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532930-97-5 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propylinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532930-96-4 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-allylinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532931-00-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propyl-6-thioinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532930-94-2 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-allylinosine 
• 296802-64-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propargylinosine 
• 532930-99-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propyl-6-thioinosine 
• 532930-95-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propylinosine 
• 1000003-68-8 C₃₉H₃₁N₅O₈ 
• 3881-21-8 2'-O-methylinosine 
• 57817-83-1 N⁶,O^2'-methyladenosine 
• 20649-46-1 2'-O,3'-O-dimethyladenosine 

Relevant articles and documents

-

-

An additional sugar component of ribonucleic acids.

-

Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations

The RNA-world hypothesis assumes that life on Earth started with small RNA molecules that catalyzed their own formation. Vital to this hypothesis is the need for prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here we show that isocyanates in combination with sodium nitrite establish methylating and carbamoylating reactivity compatible with early Earth conditions. These reactions lead to the formation of methylated and amino acid modified nucleosides that are still extant. Our data provide a plausible scenario for the chemical origin of certain noncanonical bases, which suggests that they are fossils of an early Earth.

Improved synthesis and isolation of 2'-O-methyladenosine: Effective and scalable enzymatic separation of 2'/3'-O-methyladenosine regioisomers

An efficient separation of a mixture of 2'/3'-O-methyladenosine regioisomers (1 + 2: 1:1) has been developed by selective enzymatic acylation using immobilized Pseudomonas cepacia lipase (PSL-C) in combination with acetonoxime levulinate as acyl donor. Th