BIOMAT Database Logo BIOMAT Database Logo

Efficient synthesis of 2'-C-beta-methylguanosine. 2006

Nan-Sheng Li, and Joseph A Piccirilli
Howard Hughes Medical Institute, Department of Biochemistry & Molecular Biology, University of Chicago, Chicago, Illinois 60637, USA. nli@uchicago.edu

2'-beta-Methyl nucleosides have potential value as therapeutic agents and as nucleoside analogues for exploring RNA biology. Here we develop a strategy for efficient synthesis for 2'-C-beta-methylguanosine (3). Starting from 1,2,3,5-tetra-O-benzoyl-2-C-beta-methyl-d-ribofuranose (1) and N2-acetylguanine, we obtained the title compound in two steps (78% overall yield) with high stereoselectivity (beta/alpha > 99:1) and high regioselectivity (N9/N7 > 99:1). Extension of this strategy to the classic synthesis of guanosine also resulted in high stereoselectivity (beta/alpha = 99:1) and improved regioselectivity (N9/N7 = 97:3).

UI MeSH Term Description Entries
D006151 Guanosine A purine nucleoside that has guanine linked by its N9 nitrogen to the C1 carbon of ribose. It is a component of ribonucleic acid and its nucleotides play important roles in metabolism. (From Dorland, 28th ed)
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Nan-Sheng Li, and Joseph A Piccirilli
Facile and efficient approach for the synthesis of N(2)-dimethylaminomethylene-2'-O-methylguanosine.
January 2010, Bioorganic & medicinal chemistry letters,
Nan-Sheng Li, and Joseph A Piccirilli
Novel synthesis of 2'-O-methylguanosine.
May 2003, Bioorganic & medicinal chemistry letters,
Nan-Sheng Li, and Joseph A Piccirilli
The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus.
August 2009, Bioorganic & medicinal chemistry letters,
Nan-Sheng Li, and Joseph A Piccirilli
Synthesis of 2'-C-beta-fluoromethyluridine.
March 2003, Organic letters,
Nan-Sheng Li, and Joseph A Piccirilli
Synthesis of purin-2-yl carboxylate from O6-methylguanosine.
January 2005, Nucleic acids symposium series (2004),
Nan-Sheng Li, and Joseph A Piccirilli
Highly Regioselective Methylation of Guanosine Nucleotides: An Efficient Synthesis of 7-Methylguanosine Nucleotides.
December 2019, Current protocols in nucleic acid chemistry,
Nan-Sheng Li, and Joseph A Piccirilli
Inhibition of hepatitis C virus replicon RNA synthesis by PSI-352938, a cyclic phosphate prodrug of β-D-2'-deoxy-2'-α-fluoro-2'-β-C-methylguanosine.
June 2011, Antimicrobial agents and chemotherapy,
Nan-Sheng Li, and Joseph A Piccirilli
Diastereoselective synthesis of 2',3'-dideoxy-beta-C-glucopyranosides as intermediates for the synthesis of 2',3'-dideoxy-beta-D-glucopyranosyl-C-nucleosides.
January 2007, Nucleosides, nucleotides & nucleic acids,
Nan-Sheng Li, and Joseph A Piccirilli
Synthesis of C-2 and C-4 deuterium-labeled estradiol-17 beta.
June 1983, Steroids,
Nan-Sheng Li, and Joseph A Piccirilli
Efficient synthesis of ningalin C.
August 2002, Organic letters,
Copied contents to your clipboard!