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2‐Phenanthrenyl–DNA: Synthesis, Pairing, and Fluorescence Properties by Nikolay A. Grigorenko; Christian J. Leumann is a Chemistry article available to read on EtoBox.

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## Abstract Three 2′‐phenanthrenyl‐__C__‐deoxyribonucleosides with donor (phenNH~2~), acceptor (phenNO~2~), or no (phenH) substitution on the phenanthrenyl core were synthesized and incorporated into oligodeoxyribonucleotides. Duplexes containing either one or three consecutive phenR residues, which were located opposite each other, were formed. Within these residues, the phenR residues are expected to recognize each other through interstrand stacking interactions, in much the same way as described previously for biphenyl DNA. The thermal, thermodynamic, and fluorescence properties of such duplexes were determined by UV melting analysis and fluorescence spectroscopy. Depending on the nature of the substituent, the thermal stability of single‐modified duplexes can vary between −2.7 to +11.3 °C in __T__~m~ and that of triple‐modified duplexes from +7.8 to +11.1 °C. Van′t Hoff analysis suggested that the observed higher thermodynamic stability in phenH‐ and phenNO~2~‐containing duplexes is of enthalpic origin. A single phenH or phenNO~2~ residue in a bulge position also stabilizes a corresponding duplex. If a phenNO~2~ residue is placed in a bulge position next to a base mismatch this

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Author

Nikolay A. Grigorenko; Christian J. Leumann

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2008

Language

EN

Field

Chemistry (Physical Sciences)