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Optimized synthesis of LNA uracil nucleosides |
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| Authors: | T. Santhosh Kumar Pawan Kumar Pawan K. Sharma |
| Affiliation: | a Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA b Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark c Department of Chemistry, Kurukshetra University, Kurukshetra 136119, India |
| Abstract: | A short, very high yielding, and practical synthesis of LNA uracil diol 6 has been developed from the easily accessible glycosyl donor 1. The concluding O3′-debenzylation of 5 resulted in significant reduction of the uracil moiety with many typical debenzylation conditions, while catalytic transfer hydrogenation using Pd(OH)2/C and formic acid largely suppressed this undesired side reaction. Facile access to 6 will allow full exploration of RNA-based LNA-technology applications, including polymerase-catalyzed synthesis of LNA-modified RNA-strands. |
| Keywords: | BNA Debenzylation Formic acid LNA Nucleobase reduction |
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