Abstract
Nucleosides and nucleotides are important biomolecules. Following Gilbert’s (Nature 319:618, 1986) proposal of an “RNA world,” various processes for the formation of nucleosides (from nucleobases and ribose) and the polymerization of nucleotides have been suggested. Problems associated with the formation of RNA have also been pointed out. The constituents of RNA are nucleobases, ribose, and phosphate. Ribose has five conformational isomers or conformers, each of which can react with a nucleobase. In life, however, only the β-furanose form of ribose is used. Curiously, when a nucleobase reacts with ribose in an aqueous solution, only a small amount of nucleoside with a β-ribofuranose component is detectable in the total products. Thus, the RNA world hypothesis has reached a deadlock. Here, we summarize the important points in the synthesis of nucleobases and ribose. We also describe the selective formation of nucleosides and touch on the one-pot synthesis of nucleotides.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Akouche M, Jaber M, Maurel M-C, Lambert J-F, Georgelin T (2017) Phosphoribosyl pyrophosphate: a molecular vestige of the origin of life on minerals. Angew Chem Int Ed 56:7920–7923. https://doi.org/10.1002/anie201702633
Akouche M, Jaber M, Zins E-M, Maurel M-C, Lambert J-F, Georgelin T (2016) Thermal behavior of d-ribose adsorbed on silica: effect of inorganic salt coadsorption and significance for prebiotic chemistry. Chem Eur J 22:15834–15846
Amaral AF, Marques MM, da Silva JAL, da Silva JJRF (2008) Interactions of d-ribose with polyatomic anions, and alkaline and alkaline-earth cations: possible clues to environmental synthesis conditions in the pre-RNA world. New J Chem 32:2043–2049
Becker S, Thoma I, Deutsch A, Gehrke T, Mayer P, Zipse H, Carell T (2016) A high-yielding strictly regioselective prebiotic purine nucleoside formation pathway. Science 352:833–836
Becker S, Schneider C, Okamura H, Crisp A, Amatov T, Dejmek A, Carell T (2018) Wet-dry cycles enable the parallel origin of canonical and non-canonical nucleosides by continuous synthesis. Nat. Com 9:163. https://doi.org/10.1038/s41467-017-02639-1
Benner SA, Kim H-J, Carrigan MA (2012) Asphalt, water and the prebiotic synthesis of ribose, ribonucleoside and RNA. Acc Chem Res 45:2025–2034
Cech TR (1986) A model for the RNA-catalyzed replication of RNA. Proc Natl Acad Sci USA 83:4360–4363
Chittenden GJF, Schwartz A (1976) Possible pathway for prebiotic uracil synthesis by photodehydrogenation. Nature 263:350–351
Civiš S, Szabla R, Szyja BM, Smykowski D, Ivanek O, Knížek A, Kubelik P, Šponer J, Ferus M, Šponer JE (2016) TiO2-calayzed synthesis of sugars from formaldehyde in extraterrestrial impacts on the early Earth. Sci Rep 6:23199. https://doi.org/10.1038/srep23199
Cortes SJ, Mega TL, Van Etten RL (1991) The 18O isotope shift in 13C nuclear magnetic resonance spectroscopy. 14. kinetics of oxygen exchange at the anomeric carbon of D-ribose and D-2-deoxyribose. J Org Chem 56:943–947
Ferus M, Nesvorný D, Šponer J, Kubelík P, Michalcíková R, Shestivská V, Šponer JE, Civiš S (2015) High-energy chemistry of formamide: a unified mechanism of nulcoebase formation. PNAS 112:657–662. https://doi.org/10.1073/pnas.1412072111
Fiore M, Strazewski P (2016) Bringing prebiotic nucleosides and nucleotides down to Earth. Angew Chem Int Ed 55:13930–13933. https://doi.org/10.1002/anie.201606232
Fuller WD, Sanchez RA, Orgel LE (1972) Studies in prebiotic synthesis VI. Synthesis of purine nucleosides. J Mol Biol 67:25–33
Furukawa Y, Kakegawa T (2017) Borate and the origin of RNA: a model for the precursors to life. Elements 13:261–265
Furukawa Y, Horiuchi M, Kakegawa T (2013) Selective stabilization of ribose by borate. Origins Life Evol Biosph 43:353–361
Furukawa Y, Kim HJ, Hutter D, Benner SA (2015) Abiotic regioselective phosphorylation of adenosine with borate in formamide. Astrobiology 15:259–267
Gabel NW, Ponnamperuma C (1967) Model of origin of monosaccharides. Nature 216:453–455
Gilbert W (1986) The RNA world. Nature 319:618
Hu H, Xue J, Wen X, Li W, Zhang C, Yang L, Xu Y, Zhao G, Bu X, Liu K, Chen J, Wu J (2013) Sugar-metal ion interactions: the complicated coordination structures of Cesium ion with D-ribose and myo-inositol. Inorg Chem 52:13132–13145
Kim H-J, Kim J (2019) A prebiotic synthesis of canonical pyrimidine and purine ribonucleotides. Astrobiology. https://doi.org/10.1089/ast.2018.1935
Lambert JB, Lu G, Singer SR, Kolb VM (2004) Silicate complexes of sugars in aqueous solution. J Am Chem Soc 126:9611–9625
Larralde R, Robertson MP, Miller SL (1995) Rates of decomposition of ribose and other sugars: implications for chemical evolution. Proc Natl Acad Sci USA 92:8158–8160
Maurel M-C, Leclerc F (2016) From foundation stones to life: Concepts and results. Elements 12:407–412
Menor-Salván C, Marín-Yaseli MR (2013) A new route for the prebiotic synthesis of nucleobases and hydantoins in water/ice solutions involving the photochemistry of acetylene. Chem Eur J 19:6488–6497
Miyawaki S, Murasawa K, Kobayashi K, Sawaoka AB (2000) Abiotic synthesis of guanine with high-temperature plasma. Origin Life Evol Biosph 30:557–566
Nam I, Nam HG, Zare RN (2018) Abiotic synthesis of purine and pyrimidine ribonucleosides in aqueous microdroplets. PNAS 115:36–40. https://doi.org/10.1073/pnas.1718559115
Orgel LE (2004) Prebiotic chemistry and the origin of the RNA world. Crit Rev Biochem Mol Biol 39:99–123
Powner MW, Gerland B, Sutherland JD (2009) Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature 459:239–242
Quesada-Moreno MM, Azofra LM, Avilés-Moreno JR, Alkorta I, Elguero J, López-González JJ (2013) Conformational preference and chiroptical response of carbohydrates D-ribose and 2-deoxy-D-ribose in aqueous and solid phases. J Phys Chem B 117:14599–14614
Ricardo A, Carrigan MA, Olcott AN, Benner SA (2004) Borate minerals stabilize ribose. Science 303:196
Rich A (1962) On the problems of evolution and biochemical information transfer. In: Kasha M, Pullman B (eds) Horizons in biochemistry. Academic Press, New York, pp 103–126
Robertson MP, Miller SL (1995) An efficient prebiotic synthesis of cytosine and uracil. Nature 375:772–774
Robertson MP, Joyce GF (2012) The origins of the RNA world. Cold Spring Harb Perspect Biol 4:a003608. https://doi.org/10.1101/cshperspect.a003608
Saladino R, Bizzarri BM, Botta L, Šponer J, Šponer JE, Georgelin T, Jaber M, Rigaud B, Kapralov M, Timoshenko GN, Rozanov A, Krasavin E, Timperio AM, Mauro ED (2017) Proton irradiation: a key to the challenge of N-glycosidic bond formation in a prebiotic context. Sci Rep 7:14709. https://doi.org/10.1038/s41598-017-15392-8
Saladino R, Carota E, Botta G, Kapralov M, Timoshenko GN, Rozanov AY, Krasavin E, Mauro ED (2015) Meteorite-catalyzed syntheses of nucleosides and of otherprebiotic compounds from formamide under proton irradiation. PNAS 112:E2746–E2755. https://doi.org/10.1073/pnas.1422225112
Saladino R, Neri V, Crestini C (2010) Role of clays in the preobiotic synthesis of sugar derivatives from formamide. Phil Mag 90:2329–2337
Sanchez RA, Ferris JP, Orgel LE (1966a) Conditions for purine synthesis: did prebiotic synthesis occur at low temperature? Science 153:72–73
Sanchez RA, Ferris JP, Orgel LE (1966b) Cyanoacetylene in prebiotic synthesis. Science 154:784–785
Šišak D, McCusker LB, Zandomeneghi G, Meier BH, Bläser D, Boese R, Schweizaer WB, Gilmour R, Dunitz JD (2010) The crystal structure of D-ribose- At last! Angew Chem Int Ed 49:4503–4505
Theng BKG (2018) Clay mineral catalysis of organic reactions. CRC Press, Boca Raton (FL)
Wang W, Huang F, Sun C, Liu J, Sheng X, Chen D (2017) A theoretical insight into the formation mechanisms of C/N-ribonucleosides with pyrimidine and ribose. Phys Chem Chem Phys 19:10413–10426
Xu J, Tsanakopoulou M, Magnani CJ, Szabla R, Šponer JE, Šponer J, Góra RW, Sutherland JD (2017) A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization. Nat Chem 9:303–309. https://doi.org/10.1038/NCHEM.2664
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Hashizume, H., Theng, B.K.G., van der Gaast, S., Fujii, K. (2019). Formation of Nucleosides and Nucleotides in Chemical Evolution. In: Pontarotti, P. (eds) Evolution, Origin of Life, Concepts and Methods. Springer, Cham. https://doi.org/10.1007/978-3-030-30363-1_2
Download citation
DOI: https://doi.org/10.1007/978-3-030-30363-1_2
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-30362-4
Online ISBN: 978-3-030-30363-1
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)