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2'-O-Methylguanosine

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2'-O-Methylguanosine Basic information

Product Name:
2'-O-Methylguanosine
Synonyms:
  • 2'-OMe-G
  • 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-3-methoxy-5-methylol-tetrahydrofuran-2-yl]-3H-purin-6-one
  • 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-3H-purin-6-one
  • 2-azanyl-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]-3H-purin-6-one
  • 2'-OMe Guanosine
  • 2'-O-METHYLGUANOSINE
  • 2'-O-Methyl-D-guanosine
  • 2'-O-Methyl Guanosine, >=99%
CAS:
2140-71-8
MF:
C11H15N5O5
MW:
297.27
Product Categories:
  • Nucleotides
  • Bases & Related Reagents
  • Carbohydrates & Derivatives
  • Heterocycles
  • Nucleosides
  • Modified(deoxy)nucleoside
Mol File:
2140-71-8.mol
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2'-O-Methylguanosine Chemical Properties

Melting point:
227-231°C (dec.)
Density 
1.98±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
Aqueous Base (Slightly), DMSO (Slightly),
pka
9?+-.0.20(Predicted)
form 
Powder
color 
White to Off-white
InChI
InChI=1S/C11H15N5O5/c1-20-7-6(18)4(2-17)21-10(7)16-3-13-5-8(16)14-11(12)15-9(5)19/h3-4,6-7,10,17-18H,2H2,1H3,(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1
InChIKey
OVYNGSFVYRPRCG-KQYNXXCUSA-N
SMILES
OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)[C@H](OC)[C@@H]1O
CAS DataBase Reference
2140-71-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-22
Safety Statements 
26-36-60-36/37
HS Code 
29349990
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2'-O-Methylguanosine Usage And Synthesis

Description

2''-O-Methylguanosine is a modified nucleoside that is produced in tRNAs by the action of tRNA guanosine-2’-O-methyltransferase, using S-adenosyl-L-methionine (Item Nos. 16376 | 13956) as a substrate. Through its interaction with other modified nucleosides, 2''-O-methylguanosine is thought to stabilize the structure of the tRNA. 2''-O-Methylguanosine can also be found in rRNA. Normal and modified nucleosides, including 2''-O-methylguanosine, have been shown to be secreted by a natural suppressor cell line and induce apoptosis in K562/Molt4 target cells.

Chemical Properties

White Solid

Uses

Guanosine analog. Used for preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

Definition

ChEBI: Guanosine with the hydrogen on the hydroxyl at position C-2' substituted with a methyl group.

Synthesis

8-Thio-2'-O-methylguanosine (1 mmole) is dissolved in water and the solution is heated at reflux with Raney nickel for 6 h. The product is isolated by passing the solution through a short pad of celite and is further crystallizing to afford 2'-O-methylguanosine.

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