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'-O-Me-Ado;2'-OMe Adenosine;2'-OMe Adenosine
- CBNumber
- CB5476675
- Molecular Formula
- C11H15N5O4
- Formula Weight
- 281.27
- MOL File
- 2140-79-6.mol
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)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36-24/25
- WGK Germany
- 3
- HS Code
- 29349990
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.
N-Bromosuccinimide Price
- Product number
- M2291
- Product name
- 2'-O-Methyladenosine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $421
- Updated
- 2024/03/01
- Product number
- J64922
- Product name
- 2'-O-Methyladenosine, 99%
- Packaging
- 1g
- Price
- $79.2
- Updated
- 2023/06/20
- Product number
- 16936
- Product name
- 2'-O-Methyladenosine
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 16936
- Product name
- 2'-O-Methyladenosine
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $57
- Updated
- 2024/03/01
- Product number
- 16936
- Product name
- 2'-O-Methyladenosine
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $115
- Updated
- 2024/03/01
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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View Lastest Price from 2'-O-Methyladenosine manufacturers
- 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
- 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
- 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