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Directing Effect of Substituents: meta-Directing Groups

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Related Experiment Video

Updated: Sep 2, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Substituent effects on indole universal bases in DNA.

Avi Benitah¹, Dominic F Qualley¹, Stephen A Woski¹

¹Department of Chemistry & Biochemistry, The University of Alabama, Tuscaloosa, AL, USA.

Nucleosides, Nucleotides & Nucleic Acids

|August 3, 2022

Summary

Researchers synthesized novel indole nucleosides for DNA applications. These modified nucleosides show enhanced stability and universal base properties, advancing synthetic biology and genetic research.

Keywords:

Indole 2′-deoxynucleosides duplex stabilities substituent effects universal bases

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Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes

Published on: July 6, 2016

Area of Science:

Biochemistry
Organic Chemistry
Molecular Biology

Background:

Oligodeoxynucleotides are crucial in molecular biology and synthetic biology.
The development of universal bases is key to expanding DNA applications.
Indole nucleosides offer potential as non-natural DNA components.

Purpose of the Study:

To synthesize and evaluate eleven 5-substituted-indole nucleoside residues.
To assess the universal base properties of these novel residues in DNA duplexes.
To understand the relationship between indole substituents and DNA complex stability.

Main Methods:

Synthesis of eleven 5-substituted-indole nucleoside analogs.
Incorporation of these analogs into 15-mer oligodeoxynucleotide duplexes.
UV thermal denaturation experiments to determine duplex stability.

Main Results:

All synthesized substituted indoles demonstrated greater stability than unsubstituted indole.
Electronic properties of substituents on the indole ring correlated with duplex stability.
Some residues exhibited broader base-pairing promiscuity than the 5-nitroindole control.

Conclusions:

5-substituted-indole nucleosides represent a promising class of universal bases for DNA.
Substituent electronic effects significantly influence the stability of DNA duplexes containing these residues.
Further research is needed to clarify the precise relationship between substituents and base-pairing selectivity.