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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

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.

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(2140-79-6)Related Product Information

• 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