Mechanisms of Autocatalysis

Bissette, Andrew J.; Fletcher, Stephen P.

doi:10.1002/anie.201303822

Cited by 403Origins and Evolution of LifeCellular Automata and ApplicationsSupramolecular Self-Assembly in Materials

Mechanisms of Autocatalysis

Bissette, Andrew J., Fletcher, Stephen P.·2013·Angewandte Chemie International Edition

DOI 10.1002/anie.201303822

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Abstract

Self‐replication is a fundamental concept. The idea of an entity that can repeatedly create more of itself has captured the imagination of many thinkers from von Neumann to Vonnegut. Beyond the sciences and science fiction, autocatalysis has found currency in economics and language theory, and has raised ethical fears memorably summed up by the “gray goo” trope. Autocatalysis is central to the propagation of life and intrinsic to many other biological processes. This includes the modern conception of evolution, which has radically altered humanity’s image of itself. Organisms can be thought of as imperfect self‐replicators which produce closely‐related species, allowing for selection and evolution. Hence, any consideration of self‐replication raises one of the most profound questions of all: what is life? Minimal self‐replicating systems have been studied with the aim of understanding the principles underlying living systems, allowing us to refine our concepts of biological fitness and chemical stability, self‐organization and emergence, and ultimately to discover how chemistry may become biology.

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Autocatalysis out-of-equilibrium, in its different forms (autocatalytic reactions, cyclic or network autocatalysis, and template replication), is a fundamental feature for chemical evolution to proceed towards protometabolic systems with the capacity to self-sustain and replicate themselves.
“Interestingly, we have seen that autocatalysis out-of-equilibrium, in its different forms (autocatalytic reactions, cyclic or network autocatalysis, and template replication),199 is a fundamental feature for chemical evolution to proceed towards protometabolic systems with the capacity to self-sustain and replicate themselves.”
From The protometabolic nature of prebiotic chemistry (2023) · cites this paper as [199]

Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085 · see citing works
A self-replicating peptide
Lee, D. H., Granja, J. R., Martinez, J. A., Severin, K., & Ghadiri, M. R. (1996) · Nature · doi:10.1038/382525a0 · Cited by 677 · see citing works
The Lipid World
Segré, D., Ben-Eli, D., Deamer, D. W., & Lancet, D. (2001) · Origins of life and evolution of the biosphere · doi:10.1023/a:1006746807104 · Cited by 620 · see citing works
The Origin of Biological Homochirality
Blackmond, D. G. (2010) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a002147 · Cited by 408 · see citing works
Spontaneous network formation among cooperative RNA replicators
Vaidya, N., Manapat, M. L., Chen, I. A., Xulvi-Brunet, R., Hayden, E. J., & Lehman, N. (2012) · Nature · doi:10.1038/nature11549 · Cited by 383 · see citing works
Autocatalytic synthesis of a tetranucleotide analogue
Zielinski, W. S., & Orgel, L. E. (1987) · Nature · doi:10.1038/327346a0 · Cited by 310 · see citing works
A chiroselective peptide replicator
Saghatelian, A., Yokobayashi, Y., Soltani, K., & Ghadiri, M. R. (2001) · Nature · doi:10.1038/35057238 · Cited by 310 · see citing works
Absolute Asymmetric Synthesis: A Commentary
Mislow, K. (2003) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc20030849 · Cited by 286 · see citing works
Crystalline Architectures as Templates of Relevance to the Origins of Homochirality
Weissbuch, I., & Lahav, M. (2011) · Chemical Reviews · doi:10.1021/cr1002479 · Cited by 284 · see citing works
Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis
Soai, K., Sato, I., Shibata, T., Komiya, S., Hayashi, M., Matsueda, Y., Imamura, H., Hayase, T., Morioka, H., Tabira, H., et al. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(02)00791-7 · Cited by 266 · see citing works
Amplification of Chirality from Extremely Low to Greater than 99.5 % ee by Asymmetric Autocatalysis
Sato, I., Urabe, H., Ishiguro, S., Shibata, T., & Soai, K. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200390105 · Cited by 232 · see citing works
Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality
Kawasaki, T., Matsumura, Y., Tsutsumi, T., Suzuki, K., Ito, M., & Soai, K. (2009) · Science · doi:10.1126/science.1170322 · Cited by 223 · see citing works
Sub-exponential growth and coexistence of non-enzymatically replicating templates
Szathmáry, E., & Gladkih, I. (1989) · Journal of Theoretical Biology · doi:10.1016/s0022-5193(89)80177-8 · Cited by 165 · see citing works
Matrix effect in the size distribution of fatty acid vesicles
Blöchliger, E., Blocher, M., Walde, P., & Luisi, P. L. (1998) · The Journal of Physical Chemistry B · doi:10.1021/jp981234w · Cited by 152 · see citing works
Asymmetric self-catalytic reaction. Self-production of chiral 1-(3-pyridyl)alkanols as chiral self-catalysts in the enantioselective addition of dialkylzinc reagents to pyridine-3-carbaldehyde
Soai, K., Niwa, S., & Hori, H. (1990) · Journal of the Chemical Society, Chemical Communications · doi:10.1039/c39900000982 · Cited by 146 · see citing works
Reflections on spontaneous asymmetric synthesis by amplifying autocatalysisThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
Gridnev, I. D., Serafimov, J. M., Quiney, H., & Brown, J. M. (2003) · Organic & Biomolecular Chemistry · doi:10.1039/b307382n · Cited by 140 · see citing works
Approaching Exponential Growth with a Self-Replicating Peptide
Issac, R., & Chmielewski, J. (2002) · Journal of the American Chemical Society · doi:10.1021/ja026024i · Cited by 134 · see citing works
Robust self-replication of combinatorial information via crystal growth and scission
Schulman, R., Yurke, B., & Winfree, E. (2012) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1117813109 · Cited by 132 · see citing works
Causation and the Origin of Life. Metabolism or Replication First?
Pross, A. (2004) · Origins of life and evolution of the biosphere · doi:10.1023/b:orig.0000016446.51012.bc · Cited by 122 · see citing works
Spontaneous absolute asymmetric synthesis in the presence of achiral silica gel in conjunction with asymmetric autocatalysis
Kawasaki, T., Suzuki, K., Shimizu, M., Ishikawa, K., & Soai, K. (2006) · Chirality · doi:10.1002/chir.20273 · Cited by 109 · see citing works
Functional RNAs exhibit tolerance for non-heritable 2’-5’ versus 3’-5’ backbone heterogeneity
Engelhart, A. E., Powner, M. W., & Szostak, J. W. (2013) · Nature Chemistry · doi:10.1038/nchem.1623 · Cited by 107 · see citing works
Evidence of Asymmetric Autocatalysis in Organocatalytic Reactions
Mauksch, M., Tsogoeva, S. B., Martynova, I. M., & Wei, S. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200603517 · Cited by 103 · see citing works
Unraveling the Mechanism of the Soai Asymmetric Autocatalytic Reaction by First‐Principles Calculations: Induction and Amplification of Chirality by Self‐Assembly of Hexamolecular Complexes
Schiaffino, L., & Ercolani, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802450 · Cited by 100 · see citing works
Observation of a Transient Intermediate in Soai’s Asymmetric Autocatalysis: Insights from 1H NMR Turnover in Real Time
Gehring, T., Quaranta, M., Odell, B., Blackmond, D. G., & Brown, J. M. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203398 · Cited by 99 · see citing works
Unusual Inverse Temperature Dependence on Reaction Rate in the Asymmetric Autocatalytic Alkylation of Pyrimidyl Aldehydes
Quaranta, M., Gehring, T., Odell, B., Brown, J. M., & Blackmond, D. G. (2010) · Journal of the American Chemical Society · doi:10.1021/ja103204w · Cited by 99 · see citing works
Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions
Mauksch, M., Tsogoeva, S. B., Wei, S., & Martynova, I. M. (2007) · Chirality · doi:10.1002/chir.20474 · Cited by 89 · see citing works
Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality
Kawasaki, T., Shimizu, M., Nishiyama, D., Ito, M., Ozawa, H., & Soai, K. (2009) · Chemical Communications · doi:10.1039/b908754k · Cited by 83 · see citing works
Oscillatory Symmetry Breaking in the Soai Reaction
Micskei, K., Rábai, G., Gál, E., Caglioti, L., & Pályi, G. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp803334b · Cited by 80 · see citing works
Asymmetric Autocatalysis: Triggered by Chiral Isotopomer Arising from Oxygen Isotope Substitution
Kawasaki, T., Okano, Y., Suzuki, E., Takano, S., Oji, S., & Soai, K. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102263 · Cited by 79 · see citing works
Excess mutual catalysis is required for effective evolvability
Markovitch, O., & Lancet, D. (2012) · Artificial Life · doi:10.1162/artl_a_00064 · Cited by 68 · see citing works
The design of self-replicating helical peptides
Issac, R. (2001) · Current Opinion in Structural Biology · doi:10.1016/s0959-440x(00)00233-5 · Cited by 65 · see citing works
Amplification of enantiomeric excess, mirror-image symmetry breaking and kinetic proofreading in Soai reaction models with different oligomeric orders
Micheau, J.-C., Coudret, C., Cruz, J.-M., & Buhse, T. (2012) · Physical Chemistry Chemical Physics · doi:10.1039/c2cp42041d · Cited by 62 · see citing works
Mechanism-Based Chemical Understanding of Chiral Symmetry Breaking in the Soai Reaction. A Combined Probabilistic and Deterministic Description of Chemical Reactions
Dóka, É., & Lente, G. (2011) · Journal of the American Chemical Society · doi:10.1021/ja207408y · Cited by 60 · see citing works
Evolution and self-assembly of protocells
Solé, R. V. (2009) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2008.10.004 · Cited by 59 · see citing works
Asymmetric autocatalytic Mannich reaction in the presence of water and its implication in prebiotic chemistry
Amedjkouh, M., & Brandberg, M. (2008) · Chemical Communications · doi:10.1039/b804142n · Cited by 54 · see citing works
Enantioselective Synthesis Induced by Compounds with Chirality Arising from Partially Deuterated Methyl Groups in Conjunction with Asymmetric Autocatalysis
Kawasaki, T., Ozawa, H., Ito, M., & Soai, K. (2011) · Chemistry Letters · doi:10.1246/cl.2011.320 · Cited by 45 · see citing works
Discrimination of cryptochirality in chiral isotactic polystyrene by asymmetric autocatalysis
Kawasaki, T., Hohberger, C., Araki, Y., Hatase, K., Beckerle, K., Okuda, J., & Soai, K. (2009) · Chemical Communications · doi:10.1039/b912813a · Cited by 41 · see citing works
Determination of absolute configurations of amino acids by asymmetric autocatalysis of 2-alkynylpyrimidyl alkanol as a chiral sensor
Sato, I., Ohgo, Y., Igarashi, H., Nishiyama, D., Kawasaki, T., & Soai, K. (2007) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2006.11.042 · Cited by 38 · see citing works

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Authors: Bissette, A. J., & Fletcher, S. P.
Affiliations: University of Oxford (GB)
Corresponding author: Fletcher, Stephen P.
ORCID: Bissette, Andrew J.
Fletcher, Stephen P.
Venue: Angewandte Chemie International Edition
Publisher: Wiley
Published: 2013-10-11
Volume: 52
Issue: 49
Pages: 12800-12826
ISSN: 1433-7851 (ISSN-L)
1521-3773
DOI: 10.1002/anie.201303822
OpenAlex: W2078033380
Cited by: 403
References: 38
Citations by year: 2026: 12 · 2025: 36 · 2024: 30 · 2023: 27 · 2022: 38 · 2021: 38 · 2020: 42 · 2019: 31 · 2018: 30 · 2017: 33 · 2016: 39 · 2015: 24 · 2014: 22 · 2013: 1
FWCI: 15.46
Type: journal article
Language: en
Open access: closed
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations: Angewandte Chemie International Edition (publishedVersion)
PubMed (publishedVersion)
Funders: Engineering and Physical Sciences Research Council (EP/H003711/1, 984961)
Topics: Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
Physical Sciences › Computer Science › Computational Theory and Mathematics › Cellular Automata and Applications
Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
Keywords: autocatalysis, self-replication, origin of life, evolution, concept of life, self-organization, emergence, chemical stability, biological fitness

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Mechanisms of Autocatalysis

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