Prebiotically plausible oligoribonucleotide ligation facilitated by chemoselective acetylation.

@article{Bowler2013PrebioticallyPO,
  title={Prebiotically plausible oligoribonucleotide ligation facilitated by chemoselective acetylation.},
  author={Frank R. Bowler and Christopher K. W. Chan and Colm D. Duffy and B{\'e}atrice Gerland and Saidul Islam and Matthew W. Powner and John D. Sutherland and Jianfeng Xu},
  journal={Nature chemistry},
  year={2013},
  volume={5 5},
  pages={
          383-9
        }
}
The recent synthesis of pyrimidine ribonucleoside-2',3'-cyclic phosphates under prebiotically plausible conditions has strengthened the case for the involvement of ribonucleic acid (RNA) at an early stage in the origin of life. However, a prebiotic conversion of these weakly activated monomers, and their purine counterparts, to the 3',5'-linked RNA polymers of extant biochemistry has been lacking (previous attempts led only to short oligomers with mixed linkages). Here we show that the 2… Expand
The Emergence of RNA from the Heterogeneous Products of Prebiotic Nucleotide Synthesis.
TLDR
The kinetic superiority of RNA synthesis suggests that nonenzymatic copying served as a chemical selection mechanism that allowed relatively homogeneous RNA to emerge from a complex mixture of prebiotically synthesized nucleotides and oligonucleotides. Expand
Prebiotically Plausible ‘Patching’ of RNA Backbone Cleavage Through a 3′-5′ Pyrophosphate Linkage
TLDR
It is shown here that cleavage of the phosphodiester backbone is not an endpoint for RNA replication, and 3′ -phosphate terminated RNA strands are able to participate in template-directed copying reactions with activated ribonucleotide monomers, suggesting a plausible non-enzymatic pathway for the salvage and recovery of genetic information following strand cleavage. Expand
A Mechanistic Explanation for the Regioselectivity of Nonenzymatic RNA Primer Extension
TLDR
It is found that fast and high yielding reactions selectively form 3′-5′ linkages, and in all cases with high 3′ -5′ regioselectivity, Watson–Crick base pairing between the RNA monomers and the template is observed at the extension site and at the adjacent downstream position. Expand
Selective aqueous acetylation controls the photoanomerization of α-cytidine-5'-phosphate.
TLDR
It is reported that prebiotic acetylation of the non-natural, but prebiotically plausible, ribonucleotide α-cytidine-5'-phosphate, selectively protects the vicinal diol moiety. Expand
Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides
TLDR
A divergent synthesis of pyrimidine and 8-oxo-purine nucleotides starting from a common prebiotic precursor that yields the β-ribo-stereochemistry found in the sugar phosphate backbone of biological nucleic acids is presented. Expand
Prebiotically Plausible “Patching” of RNA Backbone Cleavage through a 3′–5′ Pyrophosphate Linkage
TLDR
It is shown here that cleavage of the phosphodiester backbone is not an end point for RNA replication, and it is suggested that primer extension of 3′-phosphate-terminated RNA followed by template-directed copying represents a plausible nonenzymatic pathway for the salvage and recovery of genetic information following strand cleavage. Expand
Selective prebiotic conversion of pyrimidine and purine anhydronucleosides into Watson-Crick base-pairing arabino-furanosyl nucleosides in water
TLDR
The 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 might have played a critical role during the origins of life. Expand
Studies towards the prebiotic synthesis and phosphorylation of ribonucleotides
TLDR
The discovery of a generational node in the network of prebiotic chemistry that links the syntheses of amino acids with nucleotides 5'-phosphates suggests that these different groups of metabolites need not have arisen from separate chemistries, helping to get a better understanding of the processes governing the chemical evolution of life. Expand
Phosphorylation, Oligomerization and Self-assembly in Water Under Potential Prebiotic Conditions
TLDR
It is demonstrated that diamidophosphate (DAP), a plausible prebiotic agent produced from trimetaphosphate, efficiently (amido)phosphorylates a wide variety of (pre)biological building blocks under aqueous conditions, without the need of a condensing agent. Expand
Solid-Phase Synthesis and Hybrization Behavior of Partially 2′/3′-O-Acetylated RNA Oligonucleotides
TLDR
Two 17nt oligon nucleotides, which were synthesized possessing one specific internal 2′- or 3′-acetyl group, were used as synthetic standards in a recent report from this laboratory detailing the prebiotically plausible ligation of RNA oligonucleotides. Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 46 REFERENCES
Nonenzymatic, template-directed ligation of oligoribonucleotides is highly regioselective for the formation of 3'-5' phosphodiester bonds.
TLDR
Compared with previously characterized single nucleotide primer extension reactions, it is found that the strong preference for 3'-5'-linkages in oligonucleotide ligation is primarily due to occurence of ligation within the context of an extended Watston-Crick duplex. Expand
Pyranosyl‐RNA: Further Observations on Replication
Replication (single-turnover) of pyranosyl-RNA (p-RNA) sequences can be accomplished reliably by template-directed ligation of 2',3'-cyclophosphates of short oligomers. The ligation process wasExpand
Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions
TLDR
It is shown that activated pyrimidine ribonucleotides can be formed in a short sequence that bypasses free ribose and the nucleobases, and instead proceeds through arabinose amino-oxazoline and anhydronucleoside intermediates. Expand
Hydrolytic stability of helical RNA: a selective advantage for the natural 3',5'-bond.
  • D. A. Usher, A. McHale
  • Chemistry, Medicine
  • Proceedings of the National Academy of Sciences of the United States of America
  • 1976
TLDR
TheUse of the 3', 5'-bond, in combination with a right-handed helix, appears to have had a large selective advantage over the use of the 2', 5',bond for the storage of genetic information. Expand
Intercalation as a means to suppress cyclization and promote polymerization of base-pairing oligonucleotides in a prebiotic world
TLDR
The hypothesis that intercalators (acting as ‘molecular midwives’) could have facilitated the polymerization of the first nucleic acids and possibly helped select the first base pairs, even if only trace amounts of suitable oligomers were available is supported. Expand
Kinetic and mechanistic analysis of nonenzymatic, template-directed oligoribonucleotide ligation.
TLDR
The pH profile and relative ligation rates suggest a mechanism in which a metal-bound hydroxide ion located near the ligation junction promotes catalysis, most likely by deprotonation of the hydroxl nucleophile. Expand
Template-directed polymerization of oligoadenylates using cyanogen bromide.
TLDR
A reaction pathway was proposed in which 1 and 2 are not only intermediates for the production of 3 but also the true condensing agent in the coupling reaction of oligo(A), which increased with increase in the poly(U) concentration. Expand
Energetics of ribonuclease A catalysis. 2. Nonenzymatic hydrolysis of cytidine cyclic 2',3'-phosphate.
TLDR
Studies of the pH dependence of the nonenzymatic reaction reveal mechanisms that are first order in hydroxide concentration and second order in hydrogen ion concentration, in addition to a "water" reaction, suggesting that bifunctional catalysis occurs. Expand
Early chemical evolution of nucleic acids: a theoretical model.
TLDR
A possible cyclical pathway for early prebiotic oligonucleotide formation that involves dry-state (nontemplate) synthesis of random copolymers with mixed 2',5' and 3,5' bonds is suggested. Expand
Studies on polynucleotides
TLDR
In the in vitro amino acid incorporation experiments, however, no polyaspartate synthesis has so far been detected in the presence of poly AAG, and the new codon sequences ApApG for lysine and GpApA for glutamic acid are proposed. Expand
...
1
2
3
4
5
...