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Anthraquinones as Artificial DNA Building Blocks
Author(s) -
Bouquin Nicolas,
Malinovskii Vladimir L.,
Häner Robert
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800080
Subject(s) - anthraquinones , chemistry , anthraquinone , linker , oligonucleotide , combinatorial chemistry , fluorescence , dna , chemical stability , duplex (building) , stereochemistry , organic chemistry , biochemistry , physics , quantum mechanics , computer science , biology , operating system , botany
Abstract Synthesis and properties of oligodeoxynucleotides containing anthraquinone‐derived building blocks with flexible linkers are described. Starting from the 1,4‐, 1,5‐, 1,8‐ and 2,6‐dihydroxyanthraquinone isomers, the corresponding phosphoramidites were prepared and incorporated into oligonucleotides. The site of linker attachment was found to be of critical importance for hybrid stability. Whereas the 2,6‐isomer led to a significant stabilization, all other isomers had a negative effect on the stability of the duplex. Spectroscopic studies showed that the anthraquinones behave as fluorescence quenchers. Models of anthraquinone‐modified double‐stranded hybrids are proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)