325683-89-4

Usage

Class of compound

Nucleoside analog

Derivative of

Thymine (a nucleobase found in DNA)

Purpose

Inhibit the replication of viral DNA

Modified sugar moiety

α-L-threofuranosyl

Bulky group attached to the 3'-position of the sugar

4,4'-dimethoxytriphenylmethyl

Enhanced properties

Increased affinity for viral DNA polymerase and antiviral activity

Promising results

Inhibiting the replication of herpes simplex virus and other DNA viruses

Potential application

Development of new antiviral drugs

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 325683-84-9 1-(α-L-threofuranosyl)thymine 
• 537690-82-7 1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine 
• 325683-98-5 2,2'-anhydro-1-(α-L-threofuranosyl)thymine 
• 325684-00-2 1-(2′-O-benzoyl-α-L-threofuranosyl)thymine 
• 325683-79-2 1-(2',3'-di-O-benzoyl-α-L-threofuranosyl)thymine 

Relevant academic research and scientific papers

Efficient construction of a stable linear gene based on a TNA loop modified primer pair for gene delivery

A terminal-closed linear gene with strong exonuclease resistance and serum stability was successfully constructed by polymerase chain reaction (PCR) with an α-l-threose nucleic acid (TNA) loop modified primer pair, which can be used as an efficient gene e

A Scalable Synthesis of α-L-Threose Nucleic Acid Monomers

Recent advances in polymerase engineering have made it possible to copy information back and forth between DNA and artificial genetic polymers composed of TNA (α-l-threofuranosyl-(3′,2′) nucleic acid). This property, coupled with enhanced nuclease stability relative to natural DNA and RNA, warrants further investigation into the structural and functional properties of TNA as an artificial genetic polymer for synthetic biology. Here, we report a highly optimized chemical synthesis protocol for constructing multigram quantities of TNA nucleosides that can be readily converted to nucleoside 2′-phosphoramidites or 3′-triphosphates for solid-phase and polymerase-mediated synthesis, respectively. The synthetic protocol involves 10 chemical transformations with three crystallization steps and a single chromatographic purification, which results in an overall yield of 16-23% depending on the identity of the nucleoside (A, C, G, T).

The α-L-Threofuranosyl-(3′ → 2′)-oligonucleotide system ('TNA'): Synthesis and pairing properties

Our studies of α-L-Threofuranosyl-(3′ → 2′)-oligonucleotides ('TNA') are part of a systematic experimental inquiry into the base-pairing properties of potentially natural nucleic acid alternatives taken from RNA's close structural neighborhood. TNA is an efficient Watson-Crick base-pairing system and has the capability of informational cross-pairing with both RNA and DNA. This property, together with the system's constitutional and (presumed) generational simplicity, warrants special scrutiny of TNA in the context of the search for chemical clues to RNA's origin.