Tumir, Lidija-Marija; Grabar, Marina; Tomić, Sanja; Piantanida, Ivo (2010) The interactions of bis-phenanthridinium – nucleobase conjugates with nucleotides: adenine conjugate recognizes UMP in aqueous medium. Tetrahedron, 66 (13). pp. 2501-2513. ISSN 0040-4020
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Abstract
Among series of novel bis-phenanthridinium – nucleobase conjugates, the adenine derivative revealed high (logKs = 6.9 M-1) and selective affinity toward complementary nucleotide (UMP), accompanied by specific change in the UV/Vis spectrum of phenanthridine subunits, differing significantly from changes caused by addition of other nucleotides. High stability and selectivity of adenine-conjugate/UMP non-covalent complex is, according to the molecular modelling studies, correlated to the number of inter- and intramolecular aromatic stacking interactions between phenanthridinium subunits, covalently attached adenine and added UMP, while the selectivity of adenine-conjugate toward UMP in respect to other nucleotides is most likely the consequence of additional hydrogen bonding between UMP and adenine.
| Item Type: | Article | ||||||||||||
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| Additional Information: | NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, [vol. 66, iss. 13, (2010)] DOI: 10.1016/j.tet.2010.01.063 | ||||||||||||
| Uncontrolled Keywords: | nucleotide; bis-phenanthridine; recognition; spectroscopy | ||||||||||||
| Subjects: | NATURAL SCIENCES > Physics NATURAL SCIENCES > Chemistry > Organic Chemistry |
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| Divisions: | Division of Organic Chemistry and Biochemistry Division of Physical Chemistry |
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| Depositing User: | Ivo Piantanida | ||||||||||||
| Date Deposited: | 14 Nov 2014 07:39 | ||||||||||||
| URI: | http://fulir.irb.hr/id/eprint/1623 | ||||||||||||
| DOI: | 10.1016/j.tet.2010.01.063 |
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