Prebiotic stereoselective synthesis of purine and noncanonical pyrimidine nucleotide from nucleobases and phosphorylated carbohydrates

Proceedings of the National Academy of Sciences of the United States of America
Hyo-Joong Kim, Steven A Benner

Abstract

According to a current "RNA first" model for the origin of life, RNA emerged in some form on early Earth to become the first biopolymer to support Darwinism here. Threose nucleic acid (TNA) and other polyelectrolytes are also considered as the possible first Darwinian biopolymer(s). This model is being developed by research pursuing a "Discontinuous Synthesis Model" (DSM) for the formation of RNA and/or TNA from precursor molecules that might have been available on early Earth from prebiotic reactions, with the goal of making the model less discontinuous. In general, this is done by examining the reactivity of isolated products from proposed steps that generate those products, with increasing complexity of the reaction mixtures in the proposed mineralogical environments. Here, we report that adenine, diaminopurine, and hypoxanthine nucleoside phosphates and a noncanonical pyrimidine nucleoside (zebularine) phosphate can be formed from the direct coupling reaction of cyclic carbohydrate phosphates with the free nucleobases. The reaction is stereoselective, giving only the β-anomer of the nucleotides within detectable limits. For purines, the coupling is also regioselective, giving the N-9 nucleotide for adenine as a major produc...Continue Reading

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Citations

Nov 2, 2017·ELife·Razvan Cojocaru, Peter J Unrau
Nov 15, 2018·Chemical Communications : Chem Comm·Mikołaj J JanickiRafał Szabla
Jan 31, 2019·Astrobiology·Hyo-Joong Kim, Justin Kim
May 28, 2019·Angewandte Chemie·Jennifer S TeichertOliver Trapp
Oct 2, 2019·Angewandte Chemie·Hidenori OkamuraThomas Carell
Sep 19, 2019·Nature Chemistry·Subhendu Bhowmik, Ramanarayanan Krishnamurthy
May 20, 2020·Chemistry : a European Journal·Florian M KruseOliver Trapp
Nov 30, 2018·Life·Ulysse Pedreira-SegadeIsabelle Daniel
Jun 28, 2019·Scientific Reports·Laura E RodriguezMichael P Callahan
Feb 1, 2020·Emerging Topics in Life Sciences·Long-Fei Wu, John D Sutherland
Dec 2, 2017·Chemistry : a European Journal·Hyo-Joong Kim, Steven A Benner
Dec 13, 2018·Nature Communications·Ramanarayanan Krishnamurthy
Oct 1, 2020·Angewandte Chemie·Ana Franco, José Armando L da Silva
Nov 11, 2019·Emerging Topics in Life Sciences·Kristian Le Vay, Hannes Mutschler
Jan 10, 2020·Chemical Reviews·Mahipal YadavRamanarayanan Krishnamurthy
Dec 20, 2020·Life·Quoc Phuong TranAlbert C Fahrenbach
Feb 27, 2021·Journal of the American Chemical Society·Seohyun Chris KimJack W Szostak
Jul 21, 2020·Chemical Reviews·Kamila B MuchowskaJoseph Moran
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Aug 17, 2021·Journal of the American Chemical Society·David M FialhoNicholas V Hud
May 19, 2020·Chemical Reviews·David M FialhoNicholas V Hud
Sep 2, 2021·Journal of the American Chemical Society·Jianfeng XuJohn D Sutherland
Sep 12, 2021·Nature Communications·Tobias Dürr-MayerHenning J Jessen
Oct 12, 2021·Journal of Molecular Evolution·Harold S Bernhardt, Warren P Tate

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