RSC Advances
Paper
36 N. Kitadai and S. Maruyama, Origins of Building Blocks of
Life: A Review, Geosci. Front., 2018, 9, 1117–1153.
37 M. J. McKay and H. M. Nguyen, Recent Advances in
Transition Metal-Catalyzed Glycosylation, ACS Catal., 2012,
2, 1563–1595.
Compd., 2019, 55, 552–554; (c) S. Becker, J. Feldmann,
S. Wiedemann, H. Okamura, C. Schneider, K. Iwan,
A. Crisp, M. Rossa, T. Amatov and T. Carell, Unied
prebiotically plausible synthesis of pyrimidine and purine
RNA ribonucleotides, Science, 2019, 366, 76–82.
38 L. Botta, R. Saladino, B. M. Bizzarri, B. Cobucci-Ponzano, 50 (a) Y. Furukawa, H. J. Kim, D. Hutter and S. A. Benner,
R. Iacono, R. Avino, S. Caliro, A. Carandente, F. Lorenzini,
A. Tortora, E. Di Mauro and M. Moracci, Formamide-Based
Prebiotic Chemistry in the Phlegrean Fields, Adv. Space
Res., 2018, 62, 2372–2379.
Abiotic regioselective phosphorylation of adeno- sine with
borate in formamide, Astrobiology, 2015, 15, 1–9; (b)
G. Costanzo, R. Saladino, C. Crestini, F. Ciciriello and
E. Di Mauro, Nucleoside Phosphorylation by Phosphate
Minerals, J. Biol. Chem., 2007, 282, 16729–16735; (c)
B. Burcar, M. Pasek, M. Gull, B. J. Cafferty, F. Velasco,
39 (a) S. N. Mikhailov and E. V. Emtseva, Synthesis of
enantiomers of 3',4'-seco-2'-desoxythymidine, Chem.
Heterocycl. Compd., 1988, 24, 778–782; (b) Y. M. Ying,
W. G. Shan, W. H. Liu and Z. J. Zhan, Alkaloids and
´
N. V. Hud and C. Menor-Salvan, Darwin's Warm Little
Pond: A One-Pot Reaction for Prebiotic Phosphorylation
and the Mobilization of Phosphate from Minerals in
a Urea-Based Solvent, Angew. Chem., Int. Ed., 2016, 55,
13249–13253; (d) Y. Yamagata, H. Watanabe, M. Saitoh and
T. Namba, Volcanic Production of Polyphosphates and Its
Relevance to Prebiotic Evolution, Nature, 1991, 352, 516–551.
Nucleoside Derivatives from
a Fungal Endophyte of
Huperzia serrata, Chem. Nat. Compd., 2013, 49, 184–186; (c)
R. Huang, X. Zhou, Y. Peng, X. Yang, T. Xu and Y. Liu,
Nucleosides from the Marine Sponge Callyspongia SP,
Chem. Nat. Compd., 2011, 46, 1010–1011.
40 A. M. Downey, C. Richter, R. Pohl, R. Mahrwald and 51 (a) L. E. Orgel, Prebiotic Chemistry and the Origin of the RNA
M. Hocek, Direct One-Pot Synthesis of Nucleosides from
Unprotected or 5-O-Monoprotected D-Ribose, Org. Lett.,
2015, 17, 4604–4607.
World, Crit. Rev. Biochem. Mol. Biol., 2004, 39, 99–123; (b)
J. P. Ferris, Catalysis and Prebiotic RNA Synthesis, Origins
Life Evol. Biospheres, 1993, 23, 307–315.
41 B. Pullmann, Electronic structure, chemical reactivity, and 52 A. Biscans, Exploring the Emergence of RNA Nucleosides
basicity of purines and pyrazolopyrimidines, J. Chem. Soc.,
1959, 1621–1623.
and Nucleotides on the Early Earth, Life, 2018, 8, 57.
´
53 J. Pereto, Out of Fuzzy Chemistry: From Prebiotic Chemistry
42 A. Eschenmoser and E. Loewenthal, Chemistry of Potentially
to Metabolic Networks, Chem. Soc. Rev., 2012, 41, 5394–5403.
Prebiological Natural Products, Chem. Soc. Rev., 1992, 21, 1– 54 R. Saladino, L. Botta and E. Di Mauro, The Prevailing
16.
Catalytic Role of Meteorites in Formamide Prebiotic
43 G. T. Rogers, R. S. Shadbolt and T. L. V. Ulbricht,
Processes, Life, 2018, 8, 6.
Nucleosides. Part VII. The Reaction of Metal Salts of 55 B. M. Bizzarri, P. Manini, V. Lino, M. d'Ischia, M. Kapralov,
ˇ
ˇ
´
´
Thymine and Uracil with Tetra-Acetyl-a-Glucopyranosyl
Bromide, J. Chem. Soc. C, 1969, 2, 203–208.
E. Krasavin, K. Mrazikova, J. Sponer, J. E. Sponer, E. Di
Mauro and R. Saladino, High-Energy Proton-Beam-Induced
Polymerization/Oxygenation of Hydroxynaphthalenes on
Meteorites and Nitrogen Transfer from Urea: Modeling
Insoluble Organic Matter?, Chem.–Eur. J., 2020, 26, 14919–
14928.
¨
¨
44 H. Vorbruggen and G. Hoe, Nucleoside Syntheses, XXIII1)
On the Mechanism of Nucleoside Synthesis, Chem. Ber.,
1981, 114, 1256–1268.
45 T. Ukita, H. Hayatsu and Y. Tomita, Reinvestigation of the
Condensation Reaction of Acetobromoglucose with 56 (a) E. B. Bauer, Transition metal catalyzed glycosylation
Chloromercuri-4-Ethoxy-2(1H)-Pyrimidinone to 1-(Tetra-O-
Acetyl-b-D-Glucopyranosyl)-4-Ethoxy-2(1H)-Pyrimidinone,
Chem. Pharm. Bull., 1963, 11, 1068–1073.
reaction- an overview, Org. Biomol. Chem., 2020, 18, 9160–
9180; (b) B. M. Bizzarri, R. Saladino, I. Delno,
´
J. M. Garcıa-Ruiz and E. Di Mauro, Prebiotic organic
¨
46 H. Vorbruggen, U. Niedballa, K. Krolikiewicz, B. Bennua and
chemistry of formamide and the origin of life in planetary
conditions: What we know and what is the future, Int. J.
Mol. Sci., 2021, 22, 917.
¨
G. Hoe, in Chemistry and Biology of Nucleosides and
Nucleotides, ed. R. Harmon, R. K. Robins and L. B.
Towsend, Academic Press, New York, 1978, pp. 251–265.
57 J. Boryski, Transglycosylation Reactions of Purine
Nucleosides, 1996 Nucleosides. A Review, Nucleosides and
Nucleotides, 1996, 15, 771–791.
´
ˇ
ˇ
47 M. Ferus, A. Knızek and S. Civis, Meteorite-Catalyzed
Synthesis of Nucleosides and Other Prebiotic Compounds,
Proc. Natl. Acad. Sci. U. S. A., 2015, 112, 7109–7110.
48 H. S. Bernhardt, The RNA World Hypothesis: The Worst
Theory of the Early Evolution of Life (except for All the
Others)a, Biol. Direct, 2012, 7, 23.
49 (a) U. Kang, S. M. Ryu, D. Lee and E. K. Seo, Chemical
Constituents of the Leaves of Brassica oleracea Var.
Acephala, Chem. Nat. Compd., 2018, 54, 1023–1026; (b)
J. Ren, Y. G. Xie, Y. G. Guo, S. K. Yan and H. Z. Jin,
Chemical Constituents of Liparis viridiora, Chem. Nat.
58 (a) M. Pfaffe and R. Mahrwald, Direct glycosylation of
unprotected and unactivated carbohydrates under mild
conditions, Org. Lett., 2012, 14, 792–795; (b) X. Li and
J. Zhu, Recent Advances in Transition Metal–Catalyzed O-
Glycosylations, J. Carbohydr. Chem., 2012, 31, 284–324; (c)
G. Zhang, Q. Liu, L. Shi and J. Wang, Ferric sulfate hydrat-
catalyzed O-glycosilation using glycals with or without
microwave irradiation, Tetrahedron, 2008, 64, 339–344.
19264 | RSC Adv., 2021, 11, 19258–19264
© 2021 The Author(s). Published by the Royal Society of Chemistry