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

λmax

256 (pH 1)；258 (pH 11)

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36-60-36/37

HS Code 

29349990

2'-O-Methylguanosine Usage And Synthesis

Description

2'-O-Methylguanosine is a nucleoside that contains a 2'-O-methyl group at the 2' position of the ribose. It is a component of many nucleic acids and is usually found as a minor component in RNA. 2'-O-Methylguanosine has been shown to be an inhibitor of DNA polymerase and an activator of RNA polymerase, which may be due to its ability to form hydrogen bonds with the phosphate backbone.

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.

Physiological effects

2'-O-Methylguanosine is a modified nucleoside, it 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.

References

[1] B C PERSSON  C G  G J?ger. The spoU gene of Escherichia coli, the fourth gene of the spoT operon, is essential for tRNA (Gm18) 2’-O-methyltransferase activity.[J]. Nucleic Acids Research, 1997, 25 20: 4093-4097. DOI: 10.1093/nar/25.20.4093
[2] RYOTA YAMAGAMI. Folate-/FAD-dependent tRNA methyltransferase from Thermus thermophilus regulates other modifications in tRNA at low temperatures[J]. Genes to Cells, 2016, 21 7: 740-754. DOI: 10.1111/gtc.12376
[3] JAUNIUS URBONAVICIUS  Glenn R B  Jér?me M B Durand. Three modifications in the D and T arms of tRNA influence translation in Escherichia coli and expression of virulence genes in Shigella flexneri.[J]. Journal of Bacteriology, 2002, 184 19: 5348-5357. DOI: 10.1128/jb.184.19.5348-5357.2002
[4] MIROS?AWA Z. BARCISZEWSKA  Jan B  Tamara D Mashkova. The primary structure of lupin seed 5.8 S ribosomal RNA[J]. Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression, 1990, 1049 3: Pages 343-345. DOI: 10.1016/0167-4781(90)90108-e
[5] K SIRUM-CONNOLLY  T L M. The role of nucleotide modifications in the yeast mitochondrial ribosome.[J]. Nucleic acids symposium series, 1995, 33: 73-75.
[6] TSUNEATSU MORI . Isolation and Identification of Apoptosis Inducing Nucleosides from CD57+HLA-DRbrightNatural Suppressor Cell Line[J]. Biochemical and biophysical research communications, 1998, 251 2: Pages 416-422. DOI: 10.1006/bbrc.1998.9423

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