Design, Synthesis and Photophysical Property of a Doubly Widened Fused‐Triazolyl‐Phenanthrene Unnatural Nucleoside. Issue 12 (27th April 2017)

• Record Type: Journal Article
• Authors: Bag, Subhendu Sekhar; Das, Suman Kalyan
• Is Part Of: ChemistrySelect. Volume 2:Issue 12(2017)
• Page Start: 3577
• Page End: 3583
• Publication Date: 2017-04-27
• Subjects: Copper(I)-catalyzed azide-alkyne cycloaddition -- C−C coupling -- fused triazolyl phenanthrene -- hydrophobic nucleoside analogue -- photophysical property -- theoretical study; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201700392
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: We report herein the design and synthesis of a novel fused triazolyl phenanthrene nucleoside as a new generation of doubly widened hydrophobic unnatural nucleobase surrogate which shows interesting photphysical property with chrysene type emission. Molecular dynamics simulation using Schrodinger Macromodel reveals that regardless of the opposite natural bases, all the DNA duplexes containing the designed nucleoside, FTPhen, adopt right‐handed B‐form helix. A theoretical (DFT) study has also been carried out to know the stacking propensity in the context of DNA which reveals a good stabilizing property of the designed base via pairing with natural bases in trimeric DNA duplexes. Abstract : Fused Triazolyl Phenanthrene! is presented as a new generation of doubly widened hydrophobic unnatural nucleobase surrogate having interesting photphysical property with chrysene type emission. Theoretical study based on Molecular dynamics simulation using Schrodinger Macromodel and DFT reveal its potential stacking propensity in a duplex DNA without compromising the right‐handed B‐form helical conformations with C2′‐ endo /C3′‐ exo sugar disposition. Thus, the novel FTPhen is expected to find wide applications in chemistry, biotechnology and DNA‐based material design.