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. 2019 May;19(5):669-674.
doi: 10.1089/ast.2018.1935. Epub 2019 Jan 30.

A Prebiotic Synthesis of Canonical Pyrimidine and Purine Ribonucleotides

Hyo-Joong Kim  1 , Justin Kim  1   2
Affiliations

A Prebiotic Synthesis of Canonical Pyrimidine and Purine Ribonucleotides

Hyo-Joong Kim et al. Astrobiology. 2019 May.

Abstract

The "RNA first" model for the origin of life holds that RNA emerged spontaneously on early Earth and developed into life through its dual capabilities for genetics and catalysis. The model's central weakness is the difficulty of making its building blocks, in particular, the glycosidic bond joining nucleobases to ribose. Thus, the focus of much of the modern literature on the topic is directed toward solving this difficulty and includes elegant, though indirect, methods for making this bond. Here, we report that the glycosidic bond in canonical pyrimidine and purine ribonucleotides can be formed by direct coupling of cyclic carbohydrate phosphates with free nucleobases, all reported to be available by experimentally supported pathways that might have operated on early Earth.

Keywords: Glycosidic bond formation; Prebiotic chemistry; Ribose cyclic phosphate.

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Conflict of interest statement

No competing financial interests exist.

Figures

<b>FIG. 1.</b>
FIG. 1.
Plausible prebiotic synthetic pathway to RNA. The coupling of ribose 1,2-cyclic phosphate 3 with nucleobases yielded ribonucleoside 2′-phosphates 4–7. Ribose 1,2-cyclic phosphate 3 can be available from ribose 1 and amidotriphosphate 2 in plausible prebiotic conditions.
<b>FIG. 2.</b>
FIG. 2.
The coupling of ribose 1,2-cyclic phosphate 3 and cytosine provides cytidine 2′-phosphate 5. (A) Synthetic scheme of the coupling of ribose 1,2-cyclic phosphate 3 and cytosine to give cytidine 2′-phosphate 5. (B) HPLC trace of coupling of ribose 1,2-cyclic phosphate 3 and cytosine and its expanded view. (C) 1H NMR spectrum of the HPLC purified (collected fraction from 8 to 9 min) fraction of the coupling of 3 and cytosine, which shows the existence of cytidine 2′-phosphate 5 as a major component.
<b>FIG. 3.</b>
FIG. 3.
The coupling of ribose 1,2-cyclic phosphate 3 and uracil and guanine provides uridine 2′-phosphate 6 and guanosine 2′-phosphate 7. (A) HPLC trace of coupling of ribose 1,2-cyclic phosphate 3 and uracil and its expanded view to show the formation of uridine 2′-phosphate 6. (B) HPLC trace of coupling of ribose 1,2-cyclic phosphate 3 and guanine and its expanded view to show the formation of guanosine 2′-phosphate 7 (N9-ribofuranosylguanine 2′-phosphate) and N7-ribofuranosylguanine 2′-phosphate.
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