ORGN 171 |
| Nylon nucleic acid has a nucleic acid-based ladder polymer, in which DNA is covalently linked to a nylon polymer through the 2' position of each nucleotide. We describe the synthesis of nylon nucleic acid, using a complementary hairpin strand as a template. The synthesis efficiency of the templated approach was compared with single stranded synthesis by Maldi-TOF MS. The templated synthesis approach gave a much higher coupling yield; incompletely coupled or other byproducts were not detected. To determine the possibility of topological isomer formation during templated synthesis, nylon nucleic acid molecules were subjected to full digestion with snake venom phosphodiesterase (SVP) and bacterial alkaline phosphatase (BAP) followed by LCMS analysis. The products of digestion are unique 2' peptide linked oligonucleosides. Analysis of LCMS traces and integration provided further evidence that the templated synthesis strategy affords the correct topological isomer and is heteronucleotide-compatible. |
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |