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Issue 24, 2013
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Dibenzotetraaza[14]annulene–adenine conjugate recognizes complementary poly dT among ss-DNA/ss-RNA sequences

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Abstract

Among three novel DBTAA derivatives only the DBTAA–propyl–adenine conjugate 1 showed recognition of the consecutive oligo dT sequence by increased affinity and specific induced chirooptical response in comparison to other single stranded RNA and DNA; whereby of particular importance is the up until now unique efficient differentiation between dT and rU. At variance, its close analogue DBTAA–hexyl–adenine 2 did not reveal any selectivity between ss-DNA/RNA pointing out the important role of steric factors (linker length); moreover non-selectivity of the reference compound (3, lacking adenine) stressed the importance of adenine interactions in the 1 selectivity.

Graphical abstract: Dibenzotetraaza[14]annulene–adenine conjugate recognizes complementary poly dT among ss-DNA/ss-RNA sequences

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Article information


Submitted
14 Mar 2013
Accepted
11 Apr 2013
First published
15 Apr 2013

Org. Biomol. Chem., 2013,11, 4077-4085
Article type
Paper

Dibenzotetraaza[14]annulene–adenine conjugate recognizes complementary poly dT among ss-DNA/ss-RNA sequences

M. Radić Stojković, M. Škugor, S. Tomić, M. Grabar, V. Smrečki, Ł. Dudek, J. Grolik, J. Eilmes and I. Piantanida, Org. Biomol. Chem., 2013, 11, 4077
DOI: 10.1039/C3OB40519B

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