A Universal, Photocleavable DNA Base: Nitropiperonyl 2‘-Deoxyriboside
A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P*), has been investigated for this purpose. NPdR can be converted to its 5‘-DMTr-3‘-CE-phosphoramidite and...
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Veröffentlicht in: | Journal of organic chemistry 2001-03, Vol.66 (6), p.2067-2071 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P*), has been investigated for this purpose. NPdR can be converted to its 5‘-DMTr-3‘-CE-phosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementary strand when this P* base opposes A, T, and G was found to be 3−5 kcal/mol, but 9 kcal/mol when it opposes C. Brief irradiation (λ > 360 nm, 20 min) of DNA containing the P* base and piperidine treatment causes strand cleavage giving the 3‘- and 5‘-phosphates. Two significant recent interests, universal/non-hydrogen-bonding base analogues and photochemical backbone cleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo001594r |