Synthesis of pyrimidine nucleosides and nucleotides containing exo-4-Selenium

CARB 73

Jia Sheng, jsheng1@gsu.edu, Jozef Salon, chejxf@langate.gsu.edu, and Zhen Huang, Huang@gsu.edu. Department of Chemistry, Georgia State University, 38 Peachtree Center Ave., Atlanta, GA 30303
Selenium derivatization has potential to play more and more important roles in determining the 3-D structures of nucleic acids and their complexes with proteins through X-ray crystallography using the multiwavelength anomalous dispersion (MAD) technique, because the heavy metal co-crystallization and halogen derivatization of nucleic acids often give unsatisfied results. Based on our previous research of the selenium-modified nucleosides, especially the demonstration of the stability of the selenium functionality and its compatibility with the solid-phase synthesis, we will report for the first time the novel synthesis of thymidine phosphoramidite derivatized at the exo-4 position with selenium, and present the investigation of its incorporation into the designed oligonucleotides using solid phase synthesis.

This work is supported by NIH (GM069703) and NSF (0521553).