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 nucleoside compound synthesis method (by machine translation)
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Paragraph 0040; 0057-0060, (2017/08/27)
The invention relates to a method for synthesis of nucleoside compound, in particular of formula I and II shown in the preparation method of the compound, in the formula I and II, R1 And R2 Respectively is independently an hydroxy protecting group, preferably benzoyl, trityl, disubstituted phenyl, ethyl or tertiary butyl dimethyl silyl group; R3 And R4 Is alkyl (preferably C1 - C10 Alkyl, more preferably methyl, ethyl) or halogen (such as F, Cl or Br); B is the following arbitrary group wherein R5 Hydrogen or alkyl (preferably C1 - C10 Alkyl, more preferably methyl); X is hydroxyl or amino; Y is sulfur. (by machine translation)
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.
