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

In this study, two adenosine-like C-nucleosides (dSA and dSO2A) 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 dSA and dSO2A monomers were not recognized by adenosine deaminase (ADA). In addition, they exhibited fluorescence emissions in the UV and visible regions of dSA and dSO2A, respectively. Subsequently, dSA was converted into a phosphoramidite compound and incorporated into the ONs. The synthesized dSA-modified ONs formed a stable duplex with DNA and RNA complements comparable to natural adenosine. Furthermore, the modified ONs exhibited fluorescence emission derived from dSA. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - October 18, 2023 Category: Chemistry Authors: Fuchi, Yasufumi Kawaguchi, Miho Ito, Yuta Hari, Yoshiyuki Tags: letter Source Type: research