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Influences of Linker and Nucleoside for the Helical Self-Assembly of Perylene Along DNA Templates

Fritz, Yannic; Wagenknecht, Hans-Achim

Abstract (englisch):
Six different conjugates of perylene with 2′-deoxyuridine and with 2-amino-2′-deoxyadenosine were synthesized and applied for DNA-templated assembly in aqueous buffer solutions. They differ by the linkers ethynylene, phenylene, and phenylene–ethynylene between nucleoside and chromophore. The nucleosides were investigated as monomers in CHCl3 and dimethyl sulfoxide by optical spectroscopy. The properties of the four phenylene-linked conjugates are similar to that of perylene as reference because these linkers separate both aromatic parts. The ethynylene linker electronically couples the chromophore with the respective nucleoside and thus red shifts the absorbance. The DNA-templated assembly properties were elucidated by mixing the templates in aqueous buffer with the perylene–nucleoside conjugates from a dimethyl sulfoxide stock solution. Specific binding of the nucleosides was probed by comparing the results with dA20 and T20 as single-stranded DNA templates. Our studies reveal the structural parameters that are important for the DNA-templated assembly of perylenes. First, perylene-2′-deoxyuridine conjugates do not form DNA-templated helical assemblies, regardless of the choice of linker. ... mehr

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Verlagsausgabe §
DOI: 10.5445/IR/1000099972
Veröffentlicht am 18.11.2019
Originalveröffentlichung
DOI: 10.3389/fchem.2019.00659
Scopus
Zitationen: 1
Web of Science
Zitationen: 1
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Zitationen: 1
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2019
Sprache Englisch
Identifikator ISSN: 2296-2646
KITopen-ID: 1000099972
Erschienen in Frontiers in Chemistry
Verlag Frontiers Media
Band 7
Seiten Article no.: 659
Vorab online veröffentlicht am 22.10.2019
Nachgewiesen in Web of Science
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