333-49-3Relevant articles and documents
Selective Prebiotic Synthesis of α-Threofuranosyl Cytidine by Photochemical Anomerization
Colville, Ben W. F.,Powner, Matthew W.
, p. 10526 - 10530 (2021)
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 prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization
Xu, Jianfeng,Tsanakopoulou, Maria,Magnani, Christopher J.,Szabla, Rafa?,?poner, Judit E.,?poner, Ji?í,Góra, Robert W.,Sutherland, John D.
, p. 303 - 309 (2017/04/03)
Previous research has identified ribose aminooxazoline as a potential intermediate in the prebiotic synthesis of the pyrimidine nucleotides with remarkable properties. It crystallizes spontaneously from reaction mixtures, with an enhanced enantiomeric excess if initially enantioenriched, which suggests that reservoirs of this compound might have accumulated on the early Earth in an optically pure form. Ribose aminooxazoline can be converted efficiently into α-ribocytidine by way of 2,2'-anhydroribocytidine, although anomerization to β-ribocytidine by ultraviolet irradiation is extremely inefficient. Our previous work demonstrated the synthesis of pyrimidine β-ribonucleotides, but at the cost of ignoring ribose aminooxazoline, using arabinose aminooxazoline instead. Here we describe a long-sought route through ribose aminooxazoline to the pyrimidine β-ribonucleosides and their phosphate derivatives that involves an extraordinarily efficient photoanomerization of α-2-thioribocytidine. In addition to the canonical nucleosides, our synthesis accesses β-2-thioribouridine, a modified nucleoside found in transfer RNA that enables both faster and more-accurate nucleic acid template-copying chemistry.
Method for synthesis of cytosine
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Paragraph 0019, (2017/04/07)
The invention discloses a synthesis method of cytosine. The preparation process comprises the following steps: selecting 3-hydroxy acrylonitrile sodium salt and thiourea as raw materials; when preparing, adding a catalyst and an organic solvent to a reaction kettle, uniformly stirring, and sequentially adding the 3-hydroxy acrylonitrile sodium salt and the thiourea; raising temperature to 50-90 DEG C and carrying out a cyclization reaction for 6-10 hours to obtain a cyclization reaction solution; evaporating out the solvent in the cyclization reaction solution, and adding water and hydrochloric acid to obtain an intermediate product solution; dropping hydrogen peroxide to the intermediate product solution, raising temperature to 60-90 DEG C and preserving heat for 18-24 hours; regulating pH value through a sodium hydroxide solution, and cooling to 10-15 DEG C when the pH value is 7.0-7.5; and after cooling, filtering, washing and drying to obtain the cytosine. The synthesis method disclosed by the invention has the advantages that the process is simple in step, short in production cycle and low in cost; moreover, a raw material conversion rate is high, and the synthesized product is good in quality, high in yield, convenient in post-treatment and applicable to industrial production.
