| Synthesis of Metal Binding C-Nucleosides for Study of Novel Nucleic Acids |
| Dayle Acquilano, Joel Moore and Matthew Fountain |
| Chemically modified nucleic acids have been
utilized in the areas of drug development, nanotechnology and biotechnology.
The development of metal binding nucleotides will expand the utility of DNA in
these areas. We have sucessfully synthesized a catechol deoxyribonucleoside.
Placing catechol C-nucleotides opposite one another in a DNA oligonucleotide
duplex one can create a metal binding site between the two catechol nucleotides.
The synthesis of this modified nucleoside utilizes a tin(IV)chloride Lewis
acid to covalently attach an O,O'-bis(tert-butyldimethyl silyl) catechol to a
protected deoxyribose sugar, resulting in the formation of O,O'-bis
(tert-butyldimethylsilyl)-4-[1,2-dideoxy-3,5-O,O'-bis(ethoxycarbonyl)
-D-ribofuranos-1-yl] catechol. We have successfully synthesized the nucleoside
and are in the process of incorporating the nucleotide into a DNA duplex. The
synthesis will be expanded to include C-ribonucleotides and related C-nucleotides
capable of binding metals. The structure and properties of these DNA and RNA
molecules will be assessed to determine their feasibility in biotechnology and
nanoelectronics. |
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