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The interactions of bis-phenanthridinium – nucleobase conjugates with nucleotides: adenine conjugate recognizes UMP in aqueous medium

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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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
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
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima[202026] Ivo Piantanida098-0982914-2918MZOS
Proučavanje biomakromolekula računalnim metodama i razvoj novih algoritama[113604] Sanja Tomić098-1191344-2860MZOS
Depositing User: Ivo Piantanida
Date Deposited: 14 Nov 2014 07:39
DOI: 10.1016/j.tet.2010.01.063

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