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Titolo:
A universal, photocleavable DNA base: Nitropiperonyl 2 '-deoxyriboside
Autore:
Pirrung, MC; Zhao, XD; Harris, SV;
Indirizzi:
Duke Univ, Dept Chem, Levine Sci Res Ctr, Durham, NC 27708 USA Duke Univ Durham NC USA 27708 m, Levine Sci Res Ctr, Durham, NC 27708 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 6, volume: 66, anno: 2001,
pagine: 2067 - 2071
SICI:
0022-3263(20010323)66:6<2067:AUPDBN>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
POLYMERASE RECOGNITION; C-NUCLEOSIDES; REPLICATION; ANALOGS; OLIGODEOXYRIBONUCLEOTIDES; DIFLUOROTOLUENE; HYBRIDIZATION; PYRIMIDINE; ADENINE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
28
Recensione:
Indirizzi per estratti:
Indirizzo: Pirrung, MC Duke Univ, Dept Chem, Levine Sci Res Ctr, Durham, NC 27708 USADuke Univ Durham NC USA 27708 i Res Ctr, Durham, NC 27708 USA
Citazione:
M.C. Pirrung et al., "A universal, photocleavable DNA base: Nitropiperonyl 2 '-deoxyriboside", J ORG CHEM, 66(6), 2001, pp. 2067-2071

Abstract

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 ' -CEphosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementarystrand 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 (lambda > 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 backbonecleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors.

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Documento generato il 25/01/20 alle ore 19:26:30