ChemicalBook > CAS DataBase List > 2'-O-Methyladenosine

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
More
Less

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)
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
HS Code 
29349990
More
Less

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.

More
Less

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
More
Less

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

More
Less

2'-O-Methyladenosine Suppliers

HeFei ShenShen Medical Technology Co.,Ltd
Tel
15375050680; 15375050680
Email
gdz2.71828@163.com
Country
China
ProdList
17
Advantage
58
Wuhu Huaren Science and Technology Co., Ltd.
Tel
0553-0553-0553-5842013-801-801 18155347026
Fax
086-553-5843138
Email
jinhuaren@huarensh.com
Country
China
ProdList
295
Advantage
64
Shanghai Peinuo Biotechnology Co., Ltd
Tel
021-58648778 18217200601
Fax
QQ:99286241
Email
bush@perno.cn
Country
China
ProdList
292
Advantage
58
Nanjing Baifuli Technology Co., Ltd.
Tel
25-25-58740604 15951658055
Fax
+86-25-58356858
Email
sales@unisyn.cn
Country
China
ProdList
561
Advantage
58
Nanjing F&S Pharmatech Co., Ltd.
Tel
025-86950358 13390612682
Email
wangjinyu@fshpharm.com
Country
China
ProdList
119
Advantage
58
Nugene Biopharm Science (Hangzhou) Co., Ltd.
Tel
13326014885
Email
service@nugene.com.cn
Country
China
ProdList
53
Advantage
58
Jinan Demai Medical Technology Co., LTD
Tel
18669728830
Email
865681093@qq.com
Country
China
ProdList
523
Advantage
58
Allbiosyn Biotechnology Co.,LTD
Tel
18666985712
Email
info@allbiosyn.com
Country
China
ProdList
285
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2208
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
More
Less

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:


  • 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