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Diarylethene-modified nucleotides for switching optical properties in DNA

Barrois, S. 1; Wagenknecht, H.-A. 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


Diarylethenes were attached to the 5-position of 2’-deoxyuridine in order to yield three different photochromic nucleosides. All nucleosides were characterized with respect to their absorption and photochromic properties. Based on these results, the most promising photochromic DNA base modification was incorporated into representative oligonucleotides by using automated phosphoramidite chemistry. The switching of optical properties in DNA can be achieved selectively at 310 nm (forward) and 450 nm (backward); both wavelengths are outside the normal nucleic acid absorption range. Moreover, this nucleoside was proven to be photochemically stable and allows switching back and forth several times. These results open the way for the use of diarylethenes as photochromic compounds in DNA-based architectures.

Verlagsausgabe §
DOI: 10.5445/IR/1000043961
Veröffentlicht am 15.03.2018
DOI: 10.3762/bjoc.8.103
Zitationen: 39
Zitationen: 40
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2012
Sprache Englisch
Identifikator ISSN: 1860-5397
KITopen-ID: 1000043961
Erschienen in Beilstein journal of organic chemistry
Verlag Beilstein-Institut
Band 8
Seiten 905-914
Nachgewiesen in Web of Science
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