ORGN 509 |
Synthesis of 15N-enriched pseudouridine and derivatives
| Jean-Paul Desaulniers, Helen Mei-Ping Chui, and Christine S. Chow. Deparment of Chemistry, Wayne State University, Detroit, MI 48202 |
Pseudouridine is the most abundant modified nucleoside found in nature. This nucleoside variant is found in many types of ribonucleic acids (RNA) and has been shown to influence the three-dimensional structures of certain RNAs. One method of studying oligonucleotide structure involves enriching a given nucleoside with 15N and using NMR spectroscopy. Various synthetic methodologies have been used to synthesize 15N-labeled nucleosides. We have taken an alternative approach for the synthesis of 15N-enriched pseudouridine. Our strategy involves using a specific solvent system for the selective protection of N1 with the pivaloyloxymethyl (POM) protective group. This protection scheme allows for selective enrichment of 15N and methylation at the N3 position. Herein, we report on the synthesis of [3-15N]-3',5'-O-TIPDS-pseudouridine, and its derivative, [3-methyl-15N]- 3',5'-O-TIPDS-pseudouridine. Using phosphoramidite techniques, it is possible to incorporate this 15N-enriched nucleoside within the context of an oligonucleotide by using solid-phase techniques. |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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