| Identification | More | [Name]
2'-O-Methyladenosine | [CAS]
2140-79-6 | [Synonyms]
2'-O-METHYLADENOSINE
2'-O-Methyl-D-adenosine
5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C11H15N5O4 | [MDL Number]
MFCD00056002 | [Molecular Weight]
281.27 | [MOL File]
2140-79-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
200-202 C | [Boiling point ]
623.8±65.0 °C(Predicted) | [density ]
1.84±0.1 g/cm3(Predicted) | [storage temp. ]
−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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29349990 |
| Hazard Information | Back Directory | [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]
Adenosine analog. | [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. |
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