Prebiotic synthesis of nucleic acids and their building blocks at the atomic level – merging models and mechanisms from advanced computations and experiments

2016 ◽  
Vol 18 (30) ◽  
pp. 20047-20066 ◽  
Author(s):  
Judit E. Šponer ◽  
Rafał Szabla ◽  
Robert W. Góra ◽  
A. Marco Saitta ◽  
Fabio Pietrucci ◽  
...  

Main directions for future computational studies on the origin of the first nucleic acids is outlined.

Author(s):  
Taylor J. Santaloci ◽  
Marie E. Strauss ◽  
Ryan C. Fortenberry

Functionalizing deprotonated polycyclic aromatic hydrocarbon (PAH) anion derivatives gives rise to electronically excited states in the resulting anions. While functionalization with −OH and −C2H, done presently, does not result in the richness of electronically excited states as it does with −CN done previously, the presence of dipole-bound excited states and even some valence excited states are predicted in this quantum chemical analysis. Most notably, the more electron withdrawing −C2H group leads to valence excited states once the number of rings in the molecule reaches three. Dipole-bound excited states arise when the dipole moment of the corresponding neutral radical is large enough (likely around 2.0 D), and this is most pronounced when the hydrogen atom is removed from the functional group itself regardless of whether functionalized by a hydroxyl or enthynyl group. Deprotonatation of the hydroxyl group in the PAH creates a ketone with a delocalized highest occupied molecular orbital (HOMO) unlike deprotonation of a hydrogen on the ring where a localized lone pair on one of the carbon atoms serves as the HOMO. As a result, hydroxyl functionlization and subsequent deprotonation of PAHs creates molecules that begin to exhibit structures akin to nucleic acids. However, the electron withdrawing −C2H has more excited states than the electron donating −OH functionalized PAH. This implies that the −C2H electron withdrawing group can absorb a larger energy range of photons, which signifies an increasing likelihood of being stabilized in the harsh conditions of the interstellar medium.


Life ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 19 ◽  
Author(s):  
Harold Bernhardt

A mixture of sugar diphosphates is produced in reactions between small aldehyde phosphates catalysed by layered double hydroxide (LDH) clays under plausibly prebiotic conditions. A subset of these, pentose diphosphates, constitute the backbone subunits of nucleic acids capable of base pairing, which is not the case for the other products of these LDH-catalysed reactions. Not only that, but to date no other polymer found capable of base pairing—and therefore information transfer—has a backbone for which its monomer subunits have a plausible prebiotic synthesis, including the ribose-5-phosphate backbone subunit of RNA. Pentose diphosphates comprise the backbone monomers of pentopyranose nucleic acids, some of the strongest base pairing systems so far discovered. We have previously proposed that the first base pairing interactions were between purine nucleobase precursors, and that these were weaker and less specific than standard purine-pyrimidine interactions. We now propose that the inherently stronger pairing of pentopyranose nucleic acids would have compensated for these weaker interactions, and produced an informational polymer capable of undergoing nonenzymatic replication. LDH clays might also have catalysed the synthesis of the purine nucleobase precursors, and the polymerization of pentopyranose nucleotide monomers into oligonucleotides, as well as the formation of the first lipid bilayers.


ChemInform ◽  
2010 ◽  
Vol 23 (47) ◽  
pp. no-no
Author(s):  
M. BOEHRINGER ◽  
H.-J. ROTH ◽  
J. HUNZIKER ◽  
M. GOEBEL ◽  
R. KRISHNAN ◽  
...  

1997 ◽  
Vol 7 (6) ◽  
pp. 681-686 ◽  
Author(s):  
Stephan Jordan ◽  
Christoph Schwemler ◽  
Winfried Kosch ◽  
Axel Kretschmer ◽  
Eckhardt Schwenner ◽  
...  

2005 ◽  
Vol 2005 (3) ◽  
pp. 167-168 ◽  
Author(s):  
Gui-Rong Qu ◽  
Yong Li ◽  
Su-Hui Han

The synthesis of N1/N9- (Ethoxycarbonylmethyl)pyrimidine/purine using as synthons for peptide nucleic acids has been described. Microwave irradiation provided the desired products by alkylation of the appropriately protected natural and substituted nucleobases with ethyl bromoacetate within 4–7 min in 48–85% yields.


2013 ◽  
Vol 24 (5) ◽  
pp. 832-839 ◽  
Author(s):  
Xavier Elduque ◽  
Albert Sánchez ◽  
Kapil Sharma ◽  
Enrique Pedroso ◽  
Anna Grandas

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