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2'-O-Methyladenosine

Product Name
2'-O-Methyladenosine
CAS No.
2140-79-6
Chemical Name
2'-O-Methyladenosine
Synonyms
(2R,3R,4R,5R)-5-(6-AMino-9H-purin-9-yl)-2-(hydroxyMethyl)-4-Methoxytetrahydrofuran-3-ol;AMI;cordysinin B;OMe-rA;2'-OMe-A;2'-OMe-rA;2'-OMe-Ar;2'-OMe-Ar;2'-O-Me-dA;2'-O-Me-Ado
CBNumber
CB5476675
Molecular Formula
C11H15N5O4
Formula Weight
281.27
MOL File
2140-79-6.mol
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2'-O-Methyladenosine Property

Melting point:
200-202 C
Boiling point:
623.8±65.0 °C(Predicted)
Density 
1.84±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
DMSO (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Slightly)
form 
Powder
pka
13.13±0.70(Predicted)
color 
White to Off-white
Water Solubility 
Soluble in water.
λmax
259nm(H2O)(lit.)
InChI
InChI=1S/C11H15N5O4/c1-19-8-7(18)5(2-17)20-11(8)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
InChIKey
FPUGCISOLXNPPC-YGHVBYMHSA-N
SMILES
OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](OC)[C@@H]1O
CAS DataBase Reference
2140-79-6(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
M2291
Product name
2'-O-Methyladenosine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$421
Updated
2024/03/01
Alfa Aesar
Product number
J64922
Product name
2'-O-Methyladenosine, 99%
Packaging
1g
Price
$79.2
Updated
2023/06/20
Cayman Chemical
Product number
16936
Product name
2'-O-Methyladenosine
Purity
≥98%
Packaging
5mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
16936
Product name
2'-O-Methyladenosine
Purity
≥98%
Packaging
10mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
16936
Product name
2'-O-Methyladenosine
Purity
≥98%
Packaging
50mg
Price
$115
Updated
2024/03/01
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2'-O-Methyladenosine Chemical Properties,Usage,Production

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

2'-O-Methyladenosine is an analog of adenosine used to prepare nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

Uses

Adenosine analog.

Preparation

preparation of 2′-O-Methyladenosine
Methylation of adenosine with methyl iodide in anhydrous alkaline medium
Adenosine 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.

General Description

The 2'-O-Methyladenosine (Am) was showed to be the first nucleotide adjacent to the N7-methylguanosine (m7G) cap and it can be further modified at the N6 position by methylation to generate N6,2’-O-dimethyladenosine (m6Am) (92% chance of being modified), where the structure of m7G5'ppp5'm6AmpNp comprises 20–30% of all the structures[1]. The 2'-O-methyladenosine (Am) modification displaying the lowest level in tumor tissues[2].

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.

References

[1] Qinghai Li, Guohui Wan, Weiling He. “Methyladenosine Modification in RNAs: Classification and Roles in Gastrointestinal Cancers.” Frontiers in Oncology (2021): 586789.
[2] Qihan He. “Correction: FTSJ1 regulates tRNA 2’-O-methyladenosine modification and suppresses the malignancy of NSCLC via inhibiting DRAM1 expression.” Cell Death & Disease 11 6 (2020): 418.

2'-O-Methyladenosine Preparation Products And Raw materials

Raw materials

Preparation Products

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2'-O-Methyladenosine Suppliers

Americas 1 Canada 2 China 216 Europe 1 Germany 2 India 6 Japan 1 Slovakia 1 Switzerland 2 United Kingdom 5 United States 33 Global 270
SIGMA-RBI
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Switzerland
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AXXORA, LLC
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alexis-ch@alexis-corp.com
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Switzerland
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View Lastest Price from 2'-O-Methyladenosine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
2'-O-Methyladenosine 2140-79-6
Price
US $0.00/G
Min. Order
1G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-20
Hangzhou Verychem Science And Technology Co.Ltd
Product
2'-O-Methyladenosine 2140-79-6
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
1 tons
Release date
2024-10-21
Yunbio Tech Co.,Ltd.
Product
2'-O-Methyladenosine 2140-79-6
Price
US $0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
300KG per month
Release date
2023-03-04

2140-79-6, 2'-O-MethyladenosineRelated Search:

Guanosine NUCLEOSIDE PHOSPHORYLASE BACTERIAL 5'-Deoxyadenosylcobalamin EC 3.5.4.4 Adenosine Cyclic AMP S-ADENOSYL-L-METHIONINE Adenine 5'-Guanylic acid Adenine phosphate salt（1：1） PUROMYCIN AMINONUCLEOSIDE Vidarabine Adenine Sulfate Adenosine5'-(tetrahydrogen triphosphate), disodiuM salt, trihydrate (9CI) ADENOSINE 5'-TRIPHOSPHATASE 3-METHYLADENINE 6-Chloropurine ribonucleoside 2''-Deoxy-N6-methyladenosine

  • 2'-OMe-rA
  • 2'-O-Methyladenosine, 99.0%
  • 2'-O-Me-Ado
  • -O-Methyladenosine
  • 2-Amino-N6-(dimethylaminomethylidene)-N2-isobutyryl-2&rsquo
  • AMI
  • 2'-O-Methyladdenosine
  • (2R,3R,4R,5R)-5-(6-AMino-9H-purin-9-yl)-2-(hydroxyMethyl)-4-Methoxytetrahydrofuran-3-ol
  • 2'-O-Methyl-D-adenosine
  • 5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
  • 2'-O-METHYLADENOSINE
  • 2'-OMe-A
  • (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
  • (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-methoxy-2-methylol-tetrahydrofuran-3-ol
  • (2R,3R,4R,5R)-5-(6-azanylpurin-9-yl)-2-(hydroxymethyl)-4-methoxy-oxolan-3-ol
  • 2'-OMe Adenosine
  • cordysinin B
  • (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol
  • 2'-OMe-Ar
  • 2'-O-Methyladenosine&gt
  • Adenosine, 2'-O-methyl-
  • 2'-O-Methyladenosine USP/EP/BP
  • 2’-O-Methyl adenosine,RNA modified nucleoside Am
  • RNA modified nucleoside Am
  • -O-Methyladenosine
  • OMe-rA
  • 2'-O-Methyladenosine
  • 2'-OMe Adenosine
  • 2'-O-Me-dA
  • 2'-OMe-Ar
  • 2 ' - 0 -Methyladenosine
  • 2140-79-6
  • Nucleosides, Nucleotides, Oligonucleotides
  • Nucleoside Analogs
  • BioChemical
  • Biochemicals and Reagents
  • Biochemicals and Reagents
  • Nucleoside Analogs
  • Nucleosides, Nucleotides, Oligonucleotides
  • Bases & Related Reagents
  • Carbohydrates & Derivatives
  • Heterocycles
  • Nucleotides
  • Nucleosides
  • Modified（deoxy）nucleoside
  • Nucleosides-2'-OMe Nucleosides