Article
Synthesis and Characterization of a Modified 5'-Carboxyguanosine
Bulletin of the New Jersey Academy of Science
(2014)
Abstract
This work focuses on a multi-step synthesis procedure for the production of a modified guanosine nucleoside bearing a 5'-carboxylic acid in place of the native 5'-hydroxy group. The synthesis procedure begins with the installation of carboxybenzyloxy protecting groups at the 2'-and 3'-hydroxyls of commercially available N-Isobutyryl-5'-O-(4- dimethoxytrityl) guanosine. Following carbomylation, detritylation using 3% trichloroacetic acid liberated the 5'-hydroxyl group. In the final reaction step, the primary alcohol was selectively oxidized to the corresponding carboxylic acid using BAIB-TEMPO oxidation conditions in yields of 82%. The efficient synthesis of a 5'-carboxy derived nucleosides may prove to be useful in the bio-conjugation of RNA with other bio-molecules. The synthesis and characterization of 5'-carboxy guanosine will be discussed in this presentation for potential applications in bio-conjugation reactions.
Disciplines
Publication Date
Spring 2014
Citation Information
Pradeepkumar Patel and David Sabatino. "Synthesis and Characterization of a Modified 5'-Carboxyguanosine" Bulletin of the New Jersey Academy of Science Vol. 59 Iss. 1 (2014) p. 5 - 8 ISSN: 0028-5455 Available at: http://works.bepress.com/david_sabatino/27/