2'-O-Methyladenosine
- CAS NO.:2140-79-6
- Empirical Formula: C11H15N5O4
- Molecular Weight: 281.27
- MDL number: MFCD00056002
- EINECS: 1308068-626-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-09 19:38:33
What is 2'-O-Methyladenosine?
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
The Uses of 2'-O-Methyladenosine
2'-O-Methyladenosine is an analog of adenosine used to prepare nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.
The Uses of 2'-O-Methyladenosine
Adenosine analog.
What are the applications of Application
2′-O-Methyladenosine is an analog of adenosine
Definition
2'-O-Methyladenosine is nucleoside modification in which a methyl group is added to the 2' hydroxyl of the ribose moiety of adenosine.
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
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.
Properties of 2'-O-Methyladenosine
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 |
CAS DataBase Reference | 2140-79-6(CAS DataBase Reference) |
Safety information for 2'-O-Methyladenosine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2'-O-Methyladenosine
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 |
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