70753-61-6Relevant articles and documents
Selective Prebiotic Synthesis of α-Threofuranosyl Cytidine by Photochemical Anomerization
Colville, Ben W. F.,Powner, Matthew W.
supporting information, p. 10526 - 10530 (2021/03/30)
The structure of life's first genetic polymer is a question of intense ongoing debate. The “RNA world theory” suggests RNA was life's first nucleic acid. However, ribonucleotides are complex chemical structures, and simpler nucleic acids, such as threose nucleic acid (TNA), can carry genetic information. In principle, nucleic acids like TNA could have played a vital role in the origins of life. The advent of any genetic polymer in life requires synthesis of its monomers. Here we demonstrate a high-yielding, stereo-, regio- and furanosyl-selective prebiotic synthesis of threo-cytidine 3, an essential component of TNA. Our synthesis uses key intermediates and reactions previously exploited in the prebiotic synthesis of the canonical pyrimidine ribonucleoside cytidine 1. Furthermore, we demonstrate that erythro-specific 2′,3′-cyclic phosphate synthesis provides a mechanism to photochemically select TNA cytidine. These results suggest that TNA may have coexisted with RNA during the emergence of life.
A Scalable Synthesis of α-L-Threose Nucleic Acid Monomers
Sau, Sujay P.,Fahmi, Nour Eddine,Liao, Jen-Yu.,Bala, Saikat,Chaput, John C.
, p. 2302 - 2307 (2016/04/04)
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).
Nonenzymatic oligomerization of RNA by TNA templates
Heuberger, Benjamin O.,Switzer, Christopher
, p. 5809 - 5811 (2007/10/03)
(Diagram presented) Cytosine TNA promotes nonenzymatic, template-directed oligomerization of complementary activated rGMP, leading to selective and efficient formation of RNA products. This process models "genetic takeover" of a pre-RNA by RNA.
