Cited by 32Origins and Evolution of LifeRNA and protein synthesis mechanismsDNA and Nucleic Acid Chemistry

Homochiral Selectivity in RNA Synthesis: Montmorillonite-catalyzed Quaternary Reactions of D, L-Purine with D, L- Pyrimidine Nucleotides

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Joshi, Prakash C., Aldersley, Michael F., Ferris, James P.·2011·Origins of Life and Evolution of Biospheres

Abstract

Selective adsorption of D, L-ImpA with D, L-ImpU on the platelets of montmorillonite demonstrates an important reaction pathway for the origin of homochirality in RNA synthesis. Our earlier studies have shown that the individual reactions of D, L-ImpA or D, L-ImpU on montmorillonite catalyst produced oligomers which were only partially inhibited by the incorporation of both D- and L-enantiomers. Homochirality in these reactions was largely due to the formation of cyclic dimers that cannot elongate. We investigated the quaternary reactions of D, L-ImpA with D, L-ImpU on montmorillonite. The chain length of these oligomers increased from 9-mer to 11-mer as observed by HPLC, with a concomitant increase in the yield of linear dimers and higher oligomers in the reactions involving D, L-ImpA with D, L-ImpU as compared to the similar reactions carried out with D-enantiomers only. The formation of cyclic dimers of U was completely inhibited in the quaternary reactions. The yield of cyclic dimers of A was reduced from 60% to 10% within the dimer fraction. 12 linear dimers and 3 cyclic dimers were isolated and characterized from the quaternary reaction. The homochirality and regioselectivity of dimers were 64.1% and 71.7%, respectively. Their sequence selectivity was shown by the formation of purine-pyrimidine (54-59%) linkages, followed by purine-purine (29-32%) linkages and pyrimidine-pyrimidine (9-13%) linkages. Of the 16 trimers detected, 10 were homochiral with an overall homochirality of 73-76%. In view of the greater homochirality, sequence- and regio- selectivity, the quaternary reactions on montmorillonite demonstrate an unexpectedly favorable route for the prebiotic synthesis of homochiral RNA compared with the separate reactions of enantiomeric activated mononucleotides.

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Crossref · 10.1007/s11084-010-9222-1

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  • The co-oligomerization reaction of activated adenosine and uridine exhibited greater efficiency (up to 74% homochiral selectivity for the trimers) compared with separate reactions.

    “The co-oligomerization reaction of activated adenosine and uridine exhibited greater efficiency (up to 74% homochiral selectivity for the trimers) compared with the separate reactions of enantiomeric activated monomers.”

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Authors
Joshi, P. C., Aldersley, M. F., & Ferris, J. P.
Affiliations
Rensselaer Polytechnic Institute (US)
Corresponding author
Ferris, James P.
Venue
Origins of Life and Evolution of Biospheres
Published
2010-08-20
Volume
41
Issue
3
Pages
213-236
ISSN
  • 0169-6149 (ISSN-L)
  • 1573-0875
OpenAlex
W2077496877
Cited by
32
References
26
Citations by year
2025: 1 · 2024: 1 · 2023: 2 · 2022: 2 · 2021: 1 · 2020: 1 · 2018: 1 · 2017: 1 · 2016: 3 · 2015: 2 · 2014: 3 · 2013: 7 · 2012: 4
FWCI
2.50
Type
journal article
Language
en
Open access
Locations
  • Origins of Life and Evolution of Biospheres (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • National Science Foundation (0091892)
  • University at Albany
  • Division of Chemistry
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
Keywords
homochirality, RNA synthesis, montmorillonite, clay catalysis, prebiotic synthesis, cyclic dimers, sequence selectivity, regioselectivity, origin of life
MeSH terms
Bentonite, Catalysis, Chromatography, High Pressure Liquid, Hydrolysis, Isomerism, Models, Molecular, Phosphorylation, Purine Nucleotides, Pyrimidine Nucleotides, RNA

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