Work

4-Cyanoindole-2′-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue

Year: 2018

Type: article

Abstract: The synthesis and characterization of a universal and fluorescent nucleoside, 4-cyanoindole-2'-deoxyribonucleoside (4CIN), and its incorporation into DNA is described. 4CIN is a highly efficient fluorophore with quantum yields >0.90 in water. When incorporated into duplex DNA, 4CIN pairs equivalently with native nucleobases and has uniquely high quantum yields ranging from 0.15 to 0.31 depending on sequence and hybridization contexts, surpassing that of 2-aminopurine, the prototypical nucleoside fluorophore. 4CIN constitutes a new isomorphic nucleoside for diverse applications.

Source: Organic Letters

DOI: 10.1021/acs.orglett.8b01746

Authors: Kellan T. Passow, Daniel A. Harki

Institution: University of Minnesota

Language: English

Topic: DNA and Nucleic Acid Chemistry

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: 3M, National Cancer Institute, National Institute of General Medical Sciences

Awards: APOBEC3 STRUCTURAL STUDIES, Chemical Interrogation of Human DNA Cytosine Deaminases, Cancer Center Support Grant