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Design, Synthesis and Photophysical Property of a Doubly Widened Fused‐Triazolyl‐Phenanthrene Unnatural Nucleoside
Author(s) -
Bag Subhendu Sekhar,
Das Suman Kalyan
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700392
Subject(s) - nucleobase , phenanthrene , stacking , chrysene , chemistry , context (archaeology) , stereochemistry , dna , nucleoside , base pair , chromophore , combinatorial chemistry , computational chemistry , photochemistry , organic chemistry , biology , biochemistry , paleontology
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.