Selectivity of montmorillonite catalyzed prebiotic reactions of D, L-nucleotides
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The montmorillonite-catalyzed reactions of the 5'-phosphorimidazolides of D, L-adenosine (D, L-ImpA) (Figure 1a. N = A, R = H) and D, L-uridine (Figure 1a., N = U, R = H) yields oligomers that were as long as 7 mers and 6 mers, respectively. The reactions of dilute solutions of D-ImpA and D-ImpU under the same conditions gave oligomers as long as 9 and 8 mers respectively. This demonstrated that oligomer formation is only partially inhibited by incorporation of both the D- and L-enantiomers. The structures of the dimers, trimers and tetramer fractions formed from D, L-ImpA was investigated by selective enzymatic hydrolysis, comparison with authentic samples and mass spectrometry. Homochiral products were present in greater amounts than would be expected if theoretical amounts of each were formed. The ratio of the proportion of homochiral products to that of the amount of each expected for the dimers (cyclic and linear), trimers and tetramers, was 1.3, 1.6, and 2.1, respectively. In the D, L-ImpU reaction homochiral products did not predominate with ratios of dimers (cyclic and linear), trimers and tetramers 0.8, 0.44, and 1.4, respectively. The proportions of cyclic dimers in the dimer fraction were 52-66% with D, L-ImpA and 44-69% with D, L-ImpU. No cyclic dimers were formed in the absence of montmorillonite. The differences in the reaction products of D, L-ImpA and D, L-ImpU are likely to be due to the difference in the orientations of the activated monomers when bound to the catalytic sites on montmorillonite. The consequences of the selectivity of montmorillonite as a prebiotic catalyst are discussed.
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Deeper investigation confirmed important and modest chiral selection in the oligomerization of activated adenosine and uridine, respectively.
“Deeper investigation of these reactions confirmed important and modest chiral selection in the oligomerization of activated adenosine [535][536][537] and uridine, respectively.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [537]
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- Authors
- Joshi, P. C., Pitsch, S., & Ferris, J. P.
- Affiliations
- Rensselaer Polytechnic Institute (US)
- École Polytechnique Fédérale de Lausanne (CH)
- Corresponding author
- Ferris, James P.
- Venue
- Origins of Life and Evolution of Biospheres
- Published
- 2006-12-08
- Volume
- 37
- Issue
- 1
- Pages
- 3-26
- ISSN
- 0169-6149 (ISSN-L)
- 1573-0875
- OpenAlex
- W2075189114
- Cited by
- 43
- References
- 38
- Citations by year
- 2025: 2 · 2024: 1 · 2023: 1 · 2022: 4 · 2020: 3 · 2019: 2 · 2018: 1 · 2017: 3 · 2016: 1 · 2014: 1 · 2013: 4 · 2012: 2
- FWCI
- 1.15
- Type
- journal article
- Language
- en
- Open access
- green
- infoscience.epfl.ch
- Licence
- Locations
- Origins of Life and Evolution of Biospheres (publishedVersion)
- PubMed (publishedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion, cc-by-nc-nd)
- Funders
- National Science Foundation
- National Aeronautics and Space Administration
- 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
- montmorillonite, prebiotic catalysis, homochirality, enantioselectivity, clay mineral catalysis
- MeSH terms
- Bentonite, Biopolymers, Catalysis, Chromatography, High Pressure Liquid, Nucleotides, Mass Spectrometry
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