Acyclic 2-Ethynylnaphthalene-Modified 8-Aza-3,7-dideaza-2′-deoxyadenosine Allows Thymine Discrimination by Probing the DNA Minor Groove Environment

Abstract

Two novel acyclic environment-sensitive fluorescent nucleosides named ^ac37zA and ^an37zA are synthesized and their photophysical properties are investigated. Both ^ac37zA and ^an37zA exhibit dual fluorescence emission depending upon molecular coplanarity. Oligodeoxynucleotide probes containing ^ac37zA clearly discriminate perfectly matched thymine in target DNA strands by strong charge transfer (CT) emission in the longer wavelength region and by strong quenching of emission from the twisted conformation in the mismatched case.

Key words

acyclic nucleoside - DNA - single-nucleotide polymorphism (SNP) - adenine - thymine - solvatochromicity

Publication History

Received: 14 February 2023

Accepted after revision: 11 April 2023

Accepted Manuscript online:
11 April 2023

Article published online:
23 May 2023

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