Synthesis and Properties of 2′-Deoxyadenosine Mimics Bearing a Thieno[3,2-d]pyrimidine Ring

Abstract

A C-nucleoside with a stable C–C glycosidic bond can be used as a building block for chemically modified oligonucleotides (ONs). In this study, two adenosine-like C-nucleosides (d^SA and d^SO2A) bearing thieno[3,2-d]pyrimidine rings were designed and synthesized. These analogues were synthesized via the Heck reaction, and their properties as monomer nucleosides were investigated. Both the d^SA and d^SO2A monomers were not recognized by adenosine deaminase (ADA). In addition, they exhibited fluorescence emissions in the UV and visible regions of d^SA and d^SO2A, respectively. Subsequently, d^SA was converted into a phosphoramidite compound and incorporated into the ONs. The synthesized d^SA-modified ONs formed a stable duplex with DNA and RNA complements comparable to natural adenosine. Furthermore, the modified ONs exhibited fluorescence emission derived from d^SA.

Key words

C-nucleoside - adenosine mimic - thienopyrimidine - oligonucleotide - fluorescence

Publication History

Received: 24 July 2023

Accepted after revision: 12 September 2023

Article published online:
18 October 2023

• References and Notes

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