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2'-O-Methyladenosine

2'-O-Methyladenosine Structure
2'-O-Methyladenosine structure
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'-O-Me-Ado;2'-OMe Adenosine;-O-Methyladenosine
CBNumber:
CB5476675
Molecular Formula:
C11H15N5O4
Molecular Weight:
281.27
MDL Number:
MFCD00056002
MOL File:
2140-79-6.mol
MSDS File:
SDS
Last updated:2023-11-27 09:52:04
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2'-O-Methyladenosine Properties

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)
FDA UNII 02YX82IHZ5

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-24/25
WGK Germany  3
HS Code  29349990

2'-O-Methyladenosine price More Price(42)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical M2291 2'-O-Methyladenosine >98.0%(HPLC)(T) 2140-79-6 1g $421 2024-03-01 Buy
Alfa Aesar J64922 2'-O-Methyladenosine, 99% 2140-79-6 1g $79.2 2023-06-20 Buy
Cayman Chemical 16936 2'-O-Methyladenosine ≥98% 2140-79-6 5mg $32 2024-03-01 Buy
Cayman Chemical 16936 2'-O-Methyladenosine ≥98% 2140-79-6 10mg $57 2024-03-01 Buy
Cayman Chemical 16936 2'-O-Methyladenosine ≥98% 2140-79-6 50mg $115 2024-03-01 Buy
Product number Packaging Price Buy
M2291 1g $421 Buy
J64922 1g $79.2 Buy
16936 5mg $32 Buy
16936 10mg $57 Buy
16936 50mg $115 Buy

2'-O-Methyladenosine Chemical Properties,Uses,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 synthesis

194034-61-2
2140-79-6
Synthesis of 2'-O-Methyladenosine from 6-Chloro-9-(3,5-di-O-acetyl-2-O-methyl-β-D-ribofuranosyl)-9H-purine

2'-O-Methyladenosine Preparation Products And Raw materials

Raw materials

3'-O-Methyl-D-adenosine 6-Chloro-9-(3,5-di-O-acetyl-2-O-methyl-β-D-ribofuranosyl)-9H-purine TRIMETHYLSULFONIUM HYDROXIDE

Preparation Products

Adenosine, N-methyl-3'-O-methyl- (9CI) N(6),O(2)-Dimethyladenosine

2'-O-Methyladenosine Suppliers

Global( 253)Suppliers
Supplier Tel Email Country ProdList Advantage
Zhejiang Hengkang Pharmaceutical Co., Ltd.
+86-576-83372028 +86-18868723926 bd1@hengkangpharm.cn China 119 58
Yunbio Tech Co.,Ltd.
+86-010-60605551 +86-18046518538 yunbiochem@126.com China 321 58
Shanghai Daken Advanced Materials Co.,Ltd 		+86-371-66670886 info@dakenam.com China 15371 58
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
Nanjing Baifuli Technology Co., Ltd. 		+86-15335185688 sales@unisyn.cn CHINA 332 58
Hubei xin bonus chemical co. LTD 		86-13657291602 linda@hubeijusheng.com CHINA 22968 58
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd 		+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
Alchem Pharmtech,Inc. 		8485655694 sales@alchempharmtech.com United States 63711 58
Antai Fine Chemical Technology Co.,Limited 		18503026267 info@antaichem.com CHINA 9641 58
Supplier Advantage
Zhejiang Hengkang Pharmaceutical Co., Ltd.
58
Yunbio Tech Co.,Ltd.
58
Shanghai Daken Advanced Materials Co.,Ltd 		58
career henan chemical co 		58
Nanjing Baifuli Technology Co., Ltd. 		58
Hubei xin bonus chemical co. LTD 		58
BOC Sciences 		58
Chongqing Chemdad Co., Ltd 		58
Alchem Pharmtech,Inc. 		58
Antai Fine Chemical Technology Co.,Limited 		58

View Lastest Price from 2'-O-Methyladenosine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2'-O-Methyladenosine pictures 2024-02-06 2'-O-Methyladenosine
2140-79-6
 US $0.00 / KG 1KG 98% 300KG per month Yunbio Tech Co.,Ltd.
2'-O-Methyladenosine pictures 2024-02-06 2'-O-Methyladenosine
2140-79-6
 US $0.00 / KG 1KG 98% 300KG per month Yunbio Tech Co.,Ltd.
2'-O-Methyladenosine pictures 2023-04-04 2'-O-Methyladenosine
2140-79-6
 US $0.00-0.00 / ml 1ml 98% 1000L per month Zhejiang Hengkang Pharmaceutical Co., Ltd.

2140-79-6(2'-O-Methyladenosine)Related 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

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2'-O-Methyladdenosine 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 2'-OMe-rA 2'-O-Methyladenosine, 99.0% 2'-O-Me-Ado -O-Methyladenosine 2-Amino-N6-(dimethylaminomethylidene)-N2-isobutyryl-2&rsquo (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol 2'-OMe-Ar 2'-O-Methyladenosine> Adenosine, 2'-O-methyl- 2'-O-Methyladenosine USP/EP/BP AMI (2R,3R,4R,5R)-5-(6-AMino-9H-purin-9-yl)-2-(hydroxyMethyl)-4-Methoxytetrahydrofuran-3-ol cordysinin B 2’-O-Methyl adenosine,RNA modified nucleoside Am RNA modified nucleoside Am -O-Methyladenosine OMe-rA 2'-O-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