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 (Cordysinin B) is a member of the class of adenosines that is adenosine in which the hydroxy group at position 2' is replaced by a methoxy group. It has been isolated from the mycelia of Cordyceps sinensis. It has a role as a fungal metabolite. It is a member of adenosines and an ether. It derives from an adenosine. analogue with antiviral properties, starting material for 2'-O'-methyl nucleotides. Potential metabolite of 2'-O-Me-cAMP.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 2140-79-6 differently. You can refer to the following data:
1. 2'-O-Methyladenosine is an analog of adenosine used to prepare nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.
2. Adenosine analog.

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

Definition

2'-O-Methyladenosine is nucleoside modification in which a methyl group is added to the 2' hydroxyl of the ribose moiety of adenosine.

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

• 186581-53-3 diazomethane 
• 58-61-7 adenosine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 17287-03-5 trimethylsulphonium hydroxide 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 80-48-8 methyl p-toluene sulfonate 
• 647834-80-8 O-levulinyl acetonoxime 
• 57817-83-1 N⁶,O^2'-methyladenosine 
• 684-93-5 1-methyl-1-nitrosourea 
• 10300-22-8 3'-O-methyladenosine 
• 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 
• 74-88-4 methyl iodide 

Downstream Products

• 110764-72-2 N⁶-benzoyl-5'-(4,4'-dimethoxytrityl)-O^2'-methyladenosine 
• 85079-00-1 N⁶-benzoyl-O^2'-methyladenosine 

Relevant articles and documents

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An additional sugar component of ribonucleic acids.

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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