The effect of 5-substituent in cytosine to the photochemical C to U transition in DNA strand

Kenzo Fujimoto; Wan Licheng; Shigetaka Nakamura

doi:10.1016/j.bmcl.2021.127812

The effect of 5-substituent in cytosine to the photochemical C to U transition in DNA strand

Bioorg Med Chem Lett. 2021 Mar 1:35:127812. doi: 10.1016/j.bmcl.2021.127812. Epub 2021 Jan 22.

Authors

Kenzo Fujimoto¹, Wan Licheng², Shigetaka Nakamura²

Affiliations

¹ Department of Advanced Science and Technology, Japan Advanced Institute of Science and Technology, Asahidai 1-1, Nomi, Ishikawa 923-1292, Japan. Electronic address: kenzo@jaist.ac.jp.
² Department of Advanced Science and Technology, Japan Advanced Institute of Science and Technology, Asahidai 1-1, Nomi, Ishikawa 923-1292, Japan.

PMID: 33486052
DOI: 10.1016/j.bmcl.2021.127812

Abstract

Nucleobase editing is a powerful tool in genetic disease therapy. We have reported the photochemical transition of cytosine to uracil using an ultrafast DNA photo-cross-linking. In this study, we used cytosine derivatives such as methylcytosine, hydroxymethylcytosine, and trifluoromethylcytosine to evaluate the effect of 5-position substitution of cytosine on deamination. The conversion of cytosine to uracil was the fastest, and the conversion of trifluoromethylcytosine to trifluoromethyluracil was the slowest. The order was correlated with the hydrophilicity of the double strand containing these cytosine derivatives.

Keywords: 3-Cyanovinylcarbazole; C to U conversion; Nucleobase editing; Reversible photo-cross-linking.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cytosine / chemistry*
DNA / chemistry*
Nucleic Acid Conformation
Photochemical Processes
Uracil / chemistry*

Substances

Uracil
Cytosine
DNA