Review of α-nucleosides: from discovery, synthesis to properties and potential applications

Abstract

Nucleic acids play an important role in the genetic process of organisms; nucleosides, the building block of nucleic acids, typically exist in nature in a b configuration. As an anomer of b-nucleoside, a-nucleoside is extremely rare in nature. Because of their unique and interesting properties such as high stability, specific parallel double-stranded structure and some other biochemical properties, a-nucleosides have attracted wide attention. Various methods including but not limited to the mercuri procedure, fusion reaction and Vorbrüggen glycosylation have been used to synthesize a-nucleosides and their derivatives. However, to the best of our knowledge, there is no review that has summarized these works. Therefore, we systematically review the discovery, synthesis, properties, and potential applications of a-nucleosides in this article and look to provide a reference for subsequent studies in the coming years.

Heterochiral DNA with Complementary Strands with α‐d and β‐d Configurations: Hydrogen‐Bonded and Silver‐Mediated Base Pairs with Impact of 7‐Deazapurines Replacing Purines

“…[17] Afew a-d nucleosides are also naturally occurring. [18] The required a-d nucleosides are often side products in the convergents ynthesis of nucleosides when glycosylation is not stereospecific. Special protocolsh ave been developed to access a nucleosides, [19] and all four buildingb locks have been synthesized.…”

Anomeric and Enantiomeric 2’‐Deoxycytidines: Base Pair Stability in the Absence and Presence of Silver Ions

“…Special protocols have been developed for the synthesis of α‐ d nucleoside building blocks by stereospecific glycosylation protocols or anomerization of β‐ d nucleosides. All four α‐ d ‐nucleosides as well as building blocks for DNA synthesis have been synthesized [8] . Modified nucleosides have been incorporated in anomeric heterochiral DNA to stabilize the helix structure or to change the recognition pattern [9] .…”

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

“…The molecules of special significanceand essential components in all living organisms as well as viruses are nucleic acids that are commonly involved in a wide range of cellular functions [1,2]. The basic role of nucleic acids is a promoter of processes such as replication, transmission, and transcription of genetic data [3,4]. Nucleotides are the building blocks of nucleic acids that are composed of heterocyclic aglycone, a glycoside unit, and a phosphate group [5],while the nucleoside unit lacks the presence of a phosphate group.…”