The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Synthesis and Nonenzymic Template-Directed Polymerization of 2′-Amino-2′-deoxythreose Nucleotides, the main research direction is polymerization aminodeoxythreose nucleotide synthesis RNA DNA duplex TNA threose.Quality Control of (R)-4-Hydroxydihydrofuran-2(3H)-one.
Threose nucleic acid (TNA) is a potential alternative genetic material that may have played a role in the early evolution of life. We have developed a novel synthesis of 2′-amino modified TNA nucleosides (2′-NH2-TNA) based on a cycloaddition reaction between a glycal and an azodicarboxylate, followed by direct nucleosidation of the cycloadduct. Using this route, we synthesized the thymine and guanine 2′-NH2-TNA nucleosides in seven steps with 24% and 12% overall yield, resp. We then phosphorylated the guanine nucleoside on the 3′-hydroxyl, activated the phosphate as the 2-methylimidazolide, and tested the ability of the activated nucleotide to copy C4 RNA, DNA, and TNA templates by nonenzymic primer extension. We measured pseudo-first-order rate constants for the first nucleotide addition step of 1.5, 0.97, and 0.57 h-1 on RNA, DNA, and TNA templates, resp., at pH 7.5 and 4 °C with 150 mM NaCl, 100 mM N-(hydroxylethyl)-imidazole catalyst, and 5 mM activated nucleotide. The activated nucleotide hydrolyzed with a rate constant of 0.39 h-1, causing the polymerization reaction to stall before complete template copying could be achieved. These extension rates are more than 1 order of magnitude slower than those for amino-sugar ribonucleotides under the same conditions, and copying of the TNA template, which best represented a true self-copying reaction, was the slowest of all. The poor kinetics of 2′-NH2-TNA template copying could give insight into why TNA was ultimately not used as a genetic material by biol. systems.
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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem