Nucleoside Analogues with a 1,4‐Dioxane, 1,4‐Oxathiane or 1,4‐Oxazine Ring Structure as the Carbohydrate Fragment

Abstract

Pyrimidine and purine nucleoside analogues with a 1,4-dioxane, 1,4-0xathiane or 1,4-oxazine ring structure have been prepared from the corresponding dimesylated seconucleosides by treatment with either sodium hydroxide, sodium sulfide or primary alkylamines.

Synthesis, Structure, and Conformational Analysis of Nucleoside Analogues Comprising Six‐Membered 1,3‐Oxathiane Sugar Rings

“…The X-ray structure of the N 7 -β-OMe-purine nucleoside analogue 16 shows that the 1,3-oxathiane sugar ring adopts a perfect chair conformation with both the hydroxymethyl and the nucleobase placed in equatorial positions. [15][16][17][18][19] Six-membered 1,3-dioxane nucleoside derivatives possessing the base at the 5Ј-position (Figure 2, C) have also been reported to exhibit moderate anti-HIV activity. [12,13] cis-Substituted cyclohexenyl and cyclohexanyl nucleoside analogues were synthesized and shown to have moderate activity against the coxsackie and HSV-1 viruses (Figure 2, A).…”

Oligonucleotides with 1,4-Dioxane-Based Nucleotide Monomers

“…Formal expansion of the furanose ring of nucleosides to give nucleoside analogues with six-membered rings as sugar moiety has been a significant research field during the past few decades. , Simple cyclohexane derivatives − and nucleoside analogues with 1,4-heteroatom cyclohexanes including 1,4-dioxane, 1,4-oxathiane, 1,4-dithiane, and morpholine as the sugar moiety have also been reported, − and formal 1,4-dioxane derivatives formed by hydration of 2′,3′-dialdehyde-2′,3′- seco -nucleosides have been reported as a stable form of such dialdehydes. , None of the above-mentioned nucleoside analogues have been incorporated into oligonucleotides (ONs) as they all, but the hydrates, lack either one or two hydroxy groups to enable phosphodiester oligomerization.…”