- Selective Prebiotic Synthesis of α-Threofuranosyl Cytidine by Photochemical Anomerization
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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.
- Colville, Ben W. F.,Powner, Matthew W.
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supporting information
p. 10526 - 10530
(2021/03/30)
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- Nonenzymatic oligomerization of RNA by TNA templates
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(Diagram presented) Cytosine TNA promotes nonenzymatic, template-directed oligomerization of complementary activated rGMP, leading to selective and efficient formation of RNA products. This process models "genetic takeover" of a pre-RNA by RNA.
- Heuberger, Benjamin O.,Switzer, Christopher
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p. 5809 - 5811
(2007/10/03)
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- The α-L-Threofuranosyl-(3′ → 2′)-oligonucleotide system ('TNA'): Synthesis and pairing properties
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Our studies of α-L-Threofuranosyl-(3′ → 2′)-oligonucleotides ('TNA') are part of a systematic experimental inquiry into the base-pairing properties of potentially natural nucleic acid alternatives taken from RNA's close structural neighborhood. TNA is an efficient Watson-Crick base-pairing system and has the capability of informational cross-pairing with both RNA and DNA. This property, together with the system's constitutional and (presumed) generational simplicity, warrants special scrutiny of TNA in the context of the search for chemical clues to RNA's origin.
- Schoening, Kai-Uwe,Scholz, Peter,Wu, Xiaolin,Guntha, Sreenivasulu,Delgado, Guillermo,Krishnamurthy, Ramanarayanan,Eschenmoser, Albert
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p. 4111 - 4153
(2007/10/03)
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