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Updated: Apr 28, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
DNA-mediated electron transfer in naphthalene-modified oligonucleotides
Makiko Tanaka1, Benjamin Elias, Jacqueline K Barton
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Naphthalene-modified DNA enables efficient electron transfer, showing a preference for the 5' end. This DNA-mediated reduction is sensitive to base stacking and pathway, impacting charge transfer reactions.
Area of Science:
- Biochemistry
- Molecular Biology
- Organic Chemistry
Background:
- Oligonucleotides can be modified with chromophores to study electron transfer.
- Naphthalene is a useful chromophore for electronic coupling within DNA.
Purpose of the Study:
- To synthesize and characterize naphthalene-modified oligonucleotides for electron transfer studies.
- To investigate DNA-mediated electron transfer efficiency and directionality.
Main Methods:
- Sonogashira coupling reaction to attach naphthalene to uridine.
- Spectroscopic analysis to characterize the modified oligonucleotides.
- Photoreduction assays to measure electron transfer efficiency.
Main Results:
- Naphthalene modification via ethynyl linkage enabled electronic coupling with DNA bases.
- DNA-mediated photoreduction of 5-bromouridine occurred upon naphthalene irradiation.
- Electron transfer showed a preference towards the 5'-end of the DNA strand.
- Intrastrand and interstrand pathways exhibited different photoreduction efficiencies.
Conclusions:
- Naphthalene-modified DNA facilitates efficient, directional electron transfer.
- DNA structure and base stacking significantly influence charge transfer reactions.
- These findings advance understanding of electron transport mechanisms in DNA.
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