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. 2022 Jul 19;12(1):11828.
doi: 10.1038/s41598-022-15753-y.

Borate-guided ribose phosphorylation for prebiotic nucleotide synthesis

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Borate-guided ribose phosphorylation for prebiotic nucleotide synthesis

Yuta Hirakawa et al. Sci Rep. .

Abstract

Polymers of ribonucleotides (RNAs) are considered to store genetic information and promote biocatalytic reactions for the proto life on chemical evolution. Abiotic synthesis of ribonucleotide was successful in past experiments; nucleoside synthesis occurred first, followed by phosphorylation. These abiotic syntheses are far from biotic reactions and have difficulties as a prebiotic reaction in reacting chemicals in a specific order and purifying intermediates from other molecules in multi-steps of reactions. Another reaction, ribose phosphorylation followed by nucleobase synthesis or nucleobase addition, is close to the biotic reactions of nucleotide synthesis. However, the synthesis of ribose 5'-phosphate under prebiotically plausible conditions remains unclear. Here, we report a high-yield regioselective one-pot synthesis of ribose 5'-phosphate from an aqueous solution containing ribose, phosphate, urea, and borate by simple thermal evaporation. Of note, phosphorylation of ribose before the nucleoside formation differs from the traditional prebiotic nucleotide syntheses and is also consistent with biological nucleotide synthesis. Phosphorylation occurred to the greatest extent in ribose compared to other aldopentoses, only in the presence of borate. Borate is known to improve the stability of ribose preferentially. Geological evidence suggests the presence of borate-rich settings on the early Earth. Therefore, borate-rich evaporitic environments could have facilitated preferential synthesis of ribonucleotide coupled with enhanced stability of ribose on the early Earth.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
The present and traditional synthetic routes for abiotic nucleotide formation. Red and blue arrows represent the reactions in this study and previous studies, respectively.
Figure 2
Figure 2
Identification of ribose-phosphate and phosphorylated ribosylurea by LC–MS/MS. (a) Ribose-phosphate in acidified product solution (m/z: 229.1). (b) Ribosylurea phosphate in acidified product solution (m/z: 271.1). (c) Ribose-phosphate after acid hydrolysis (m/z: 229.1). (d) Fragment mass spectrum of ribose 5′-phosphate formed in the reaction containing boric acid. The m/z of 229 and 97 are ribose-phosphate and phosphate, respectively. (e) Fragment mass spectrum of standard ribose 5′-phosphate (STD).
Figure 3
Figure 3
Borate-guided one-pot regioselective phosphorylation of ribose at 5′-hydroxyl position.
Figure 4
Figure 4
Selective phosphorylation of ribose in borate containing reaction mixture. (a) Mass chromatograms and yields of pentose-phosphates in experiments containing borate (m/z: 229.1). (b) Fragment mass spectrum for ribose 5′-phosphate. (c) Fragment mass spectrum for arabinose-phosphates. (d) Fragment mass spectrum for xylose-phosphates. (e) Fragment mass spectrum for lyxose-phosphates.

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References

    1. Walter G. The RNA world. Nature. 1986;319:618.
    1. Joyce GF. RNA evolution and the origins of life. Nature. 1989;338:217–224. doi: 10.1038/338217a0. - DOI - PubMed
    1. Fuller WD, Sanchez RA, Orgel LE. Studies in prebiotic synthesis. VII. J. Mol. Evol. 1972;1:249–257. doi: 10.1007/BF01660244. - DOI - PubMed
    1. Powner MW, Gerland B, Sutherland JD. Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature. 2009;459:239–242. doi: 10.1038/nature08013. - DOI - PubMed
    1. Stairs S, Nikmal A, Bǔar DK, Zheng SL, Szostak JW, Powner MW. Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides. Nat. Commun. 2017;8:15270. doi: 10.1038/ncomms15270. - DOI - PMC - PubMed

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