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| | 2'-O-Methyladenosine Basic information |
| | 2'-O-Methyladenosine Chemical 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) |
| | 2'-O-Methyladenosine Usage And Synthesis |
| 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. | | 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. |
| | 2'-O-Methyladenosine Preparation Products And Raw materials |
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