2'-O-Methylguanosine

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.