Related Experiment Video
Updated: Oct 2, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Major adenine products from 2-methyl-1,4-naphthoquinone-sensitized photoirradiation at 365 nm
Yinsheng Wang1, Zhenjiu Liu, Cynthia Dixon
1Department of Chemistry, 027, University of California at Riverside, Riverside, CA 92521-0403, USA. yinsheng.weng@ucr.edu
Abstract:
In this article we report the isolation and characterization of major products of adenine in dinucleoside monophosphates upon 2-methyl-1,4-naphthoquinone (menadione)-sensitized UVA irradiation. Our results show that the major products form via the coupling between the menadione moiety and the exocyclic amino group of adenine. Similar reactions were not observed for cytosine. To our knowledge, this is the first report about the direct reaction between a DNA base and a photosensitizer under 365-nm ultraviolet light irradiation. Our results are consistent with previous observation showing that N(6) radical formed on adenine upon UVA irradiation.
Related Concept Videos
2° Amines to N-Nitrosamines: Reaction with NaNO2
Nucleophilic Aromatic Substitution: Elimination–Addition
Physical Properties of Amines
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Cycloaddition Reactions: MO Requirements for Photochemical Activation
