TY - JOUR
T1 - Selective prebiotic conversion of pyrimidine and purine anhydronucleosides into Watson-Crick base-pairing arabino-furanosyl nucleosides in water
AU - Roberts, Samuel J.
AU - Szabla, Rafał
AU - Todd, Zoe R.
AU - Stairs, Shaun
AU - Bučar, Dejan Krešimir
AU - Šponer, Jiří
AU - Sasselov, Dimitar D.
AU - Powner, Matthew W.
N1 - Funding Information:
This work was supported in part by the Simons Foundation (318881 to M.W.P., 494188 to R.S. and 290360 to D.D.S.) and the Engineering and Physical Sciences Research Council (EP/K004980/1 to M.W.P.). The authors thank Dr. K. Karu for assistance with mass spectrometry and Dr. A.E. Aliev for assistance with NMR spectroscopy. Z.R.T. and D.D.S. would like to thank D. Bucher, and to acknowledge the Harvard Origins of Life Initiative.
Publisher Copyright:
© 2018, The Author(s).
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2018/10/4
Y1 - 2018/10/4
N2 - Prebiotic nucleotide synthesis is crucial to understanding the origins of life on Earth. There are numerous candidates for life’s first nucleic acid, however, currently no prebiotic method to selectively and concurrently synthesise the canonical Watson–Crick base-pairing pyrimidine (C, U) and purine (A, G) nucleosides exists for any genetic polymer. Here, we demonstrate the divergent prebiotic synthesis of arabinonucleic acid (ANA) nucleosides. The complete set of canonical nucleosides is delivered from one reaction sequence, with regiospecific glycosidation and complete furanosyl selectivity. We observe photochemical 8-mercaptopurine reduction is efficient for the canonical purines (A, G), but not the non-canonical purine inosine (I). Our results demonstrate that synthesis of ANA may have been facile under conditions that comply with plausible geochemical environments on early Earth and, given that ANA is capable of encoding RNA/DNA compatible information and evolving to yield catalytic ANA-zymes, ANA may have played a critical role during the origins of life.
AB - Prebiotic nucleotide synthesis is crucial to understanding the origins of life on Earth. There are numerous candidates for life’s first nucleic acid, however, currently no prebiotic method to selectively and concurrently synthesise the canonical Watson–Crick base-pairing pyrimidine (C, U) and purine (A, G) nucleosides exists for any genetic polymer. Here, we demonstrate the divergent prebiotic synthesis of arabinonucleic acid (ANA) nucleosides. The complete set of canonical nucleosides is delivered from one reaction sequence, with regiospecific glycosidation and complete furanosyl selectivity. We observe photochemical 8-mercaptopurine reduction is efficient for the canonical purines (A, G), but not the non-canonical purine inosine (I). Our results demonstrate that synthesis of ANA may have been facile under conditions that comply with plausible geochemical environments on early Earth and, given that ANA is capable of encoding RNA/DNA compatible information and evolving to yield catalytic ANA-zymes, ANA may have played a critical role during the origins of life.
U2 - 10.1038/s41467-018-06374-z
DO - 10.1038/s41467-018-06374-z
M3 - Article
C2 - 30287815
AN - SCOPUS:85054448955
VL - 9
JO - Nature Communications
JF - Nature Communications
SN - 2041-1723
M1 - 4073
ER -