Anthraquinones as artificial DNA building blocks

作者:Bouquin Nicolas; Malinovskii Vladimir L; Haener Robert
来源:European Journal of Organic Chemistry, 2008, 2008(13): 2213-2219.
DOI:10.1002/ejoc.200800080

摘要

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.

  • 出版日期2008-5