Kinetic analysis of artificial peptide self-replication. Part II: The heterochiral case
Abstract
A kinetic model has been designed to describe and to analyze the stereoselective behavior of a recently discovered heterochiral template-directed peptide self-replicator by Ghadiri and co-workers [Nature 409 (2001) 797-801]. It turned out that previous assumptions stating that exclusively homochiral species participate in a stereoselective and autocatalytic pathway and that heterochiral species originate only from uncatalyzed background reactions could not be validated by our model. On the contrary, excellent fitting of experimental data indicated that the whole combinatorial variety of possible cross-catalytic processes involving L- and D- peptide species play an important role and need to be taken into account. The system shows no net creation of chiral matter but only a redistribution of the initially present chiral material. Both, the separation of an optically inactive meso-type template dimer and a slight chiroselective autocatalytic effect, contribute to a predicted amplification of enantiomeric excess that, in some cases, can simultaneously result in a substantial amount of optically active matter.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The replicator entails a stereoselective autocatalytic cycle, for which all bimolecular steps are faster for matched versus unmatched pairs of substrate enantiomers.
“The replicator entails a stereoselective autocatalytic cycle, for which all bimolecular steps are faster for matched versus unmatched pairs of substrate enantiomers”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [542]
Cites
Chiral Symmetry Breaking in Sodium Chlorate Crystallization
Kondepudi, D. K., Kaufman, R. J., & Singh, N. (1990) · Science · doi:10.1126/science.250.4983.975 · Cited by 965 · see citing works
On spontaneous asymmetric synthesis
Frank, F. C. (1953) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(53)90082-1 · Cited by 905 · see citing works
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 origin and amplification of biomolecular chirality
Bonner, W. A. (1991) · Origins of life and evolution of the biosphere · doi:10.1007/bf01809580 · Cited by 557 · see citing works
Orgel, L. E. (1992) · Nature · doi:10.1038/358203a0 · Cited by 535 · see citing works
Weak neutral currents and the origin of biomolecular chirality
Kondepudi, D. K., & Nelson, G. W. (1985) · Nature · doi:10.1038/314438a0 · Cited by 375 · see citing works
Chiral Autocatalysis, Spontaneous Symmetry Breaking, and Stochastic Behavior
Kondepudi, D. K., & Asakura, K. (2001) · Accounts of Chemical Research · doi:10.1021/ar010089t · Cited by 363 · see citing works
Enantioselective Automultiplication of Chiral Molecules by Asymmetric Autocatalysis
Soai, K., Shibata, T., & Sato, I. (2000) · Accounts of Chemical Research · doi:10.1021/ar9900820 · Cited by 333 · 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
Minimal Replicator Theory I: Parabolic Versus Exponential Growth
von Kiedrowski, G. (1993) · Bioorganic Chemistry Frontiers · doi:10.1007/978-3-642-78110-0_4 · Cited by 212 · see citing works
Nonlinear stereochemical effects in asymmetric reactions
Ávalos, M., Babiano, R., Cintas, P., Jiménez, J., & Palacios, J. C. (1997) · Tetrahedron Asymmetry · doi:10.1016/s0957-4166(97)00375-3 · Cited by 166 · see citing works
From parity to chirality: chemical implications revisited
Ávalos, M., Babiano, R., Cintas, P., Jiménez, J. L., & Palacios, J. C. (2000) · Tetrahedron Asymmetry · doi:10.1016/s0957-4166(00)00265-2 · Cited by 161 · see citing works
Minimal self-replicating systems
Robertson, A., Sinclair, A. J., & Philp, D. (2000) · Chemical Society Reviews · doi:10.1039/a803602k · Cited by 131 · see citing works
Origin of the homochirality of biomolecules
Keszthelyi, L. (1995) · Quarterly Reviews of Biophysics · doi:10.1017/s0033583500003309 · Cited by 128 · see citing works
Peptide Self‐Replication Via Template‐Directed Ligation
Severin, K., Lee, D. H., Martinez, J. A., & Ghadiri, M. R. (1997) · Chemistry - A European Journal · doi:10.1002/chem.19970030706 · Cited by 110 · see citing works
Templates, autocatalysis and molecular replication
Bag, B. G., & von Kiedrowski, G. (1996) · Pure and Applied Chemistry · doi:10.1351/pac199668112145 · Cited by 98 · see citing works
(1999) · Elsevier eBooks · doi:10.1016/b978-0-08-043404-9.x5000-1 · Cited by 97 · see citing works
Kinetic Analysis of the Rebek Self-Replicating System: Is There a Controversy?
Reinhoudt, D. N., Rudkevich, D. M., & de Jong, F. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960324g · Cited by 83 · 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
Helical peptide and protein design
Micklatcher, C., & Chmielewski, J. A. (1999) · Current Opinion in Chemical Biology · doi:10.1016/s1367-5931(99)00031-9 · Cited by 55 · see citing works
Crystallization of Calcite Spherules around Designer Nuclei
Küther, J., Seshadri, R., & Tremel, W. (1998) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(19981116)37:21 · Cited by 53 · see citing works
Review Chiral resolutions, asymmetric synthesis and amplification of enantiomeric excess
de Min., M., Lévy, G., & Micheau, J. C. (1988) · Journal de Chimie Physique · doi:10.1051/jcp/1988850603 · Cited by 27 · see citing works
Self-citationKinetics of chiral resolution in stirred crystallization of D/L-glutamic acid
Buhse, T., Kondepudi, D. K., & Hoskins, B. J. (1999) · Chirality · doi:10.1002/(sici)1520-636x(1999)11:4 · Cited by 27 · see citing works
Self-citationChiral symmetry breaking: Experimental results and computer analysis of a liquid‐phase autoxidation
Buhse, T., Lavabre, D., Micheau, J. C., & Thiemann, W. (1993) · Chirality · doi:10.1002/chir.530050512 · Cited by 22 · see citing works
Self-citationConglomerate crystallization and chiral discrimination phenomena: In vivo and in vitro
Bernal, I. (1992) · Journal of Chemical Education · doi:10.1021/ed069p468 · Cited by 16 · see citing works
Kinetic analysis of artificial peptide self-replication. Part I: The homochiral case
Rivera-Islas, J., Pimienta, V., Micheau, J. C., & Buhse, T. (2003) · Biophysical Chemistry · doi:10.1016/s0301-4622(02)00248-x · Cited by 14 · see citing works
Self-citation
Flagged first, then by citations
Cited by
Sorted by citations
Wang, F., Lü, C., & Willner, I. (2014) · Chemical Reviews · doi:10.1021/cr400354z · Cited by 647 · see citing works
Buhse, T., Cruz, J.-M., Noble-Terán, M. E., Hochberg, D., Ribó, J. M., Crusats, J., & Micheau, J.-C. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00819 · Cited by 189 · see citing works
Self-citationPossible chemical and physical scenarios towards biological homochirality
Sallembien, Q., Bouteiller, L., Crassous, J., & Raynal, M. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01179k · Cited by 186 · see citing works
The Road to Non‐Enzymatic Molecular Networks
Dadon, Z., Wagner, N., & Ashkenasy, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200702552 · Cited by 141 · see citing works
Systems Chemistry: Logic Gates, Arithmetic Units, and Network Motifs in Small Networks
Wagner, N., & Ashkenasy, G. (2008) · Chemistry - A European Journal · doi:10.1002/chem.200801850 · Cited by 109 · see citing works
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
Self-citationSymmetry and order in systems chemistry
Wagner, N., & Ashkenasy, G. (2009) · The Journal of Chemical Physics · doi:10.1063/1.3118649 · Cited by 45 · see citing works
C−H Bond Activation of Benzene by Unsaturated η2-Cyclopropene and η2-Benzyne Complexes of Niobium
Boulho, C., Oulie, P., Vendier, L., Étienne, M., Pimienta, V., Locati, A., Bessac, F., Maseras, F., Pantazis, D. A., & McGrady, J. E. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1061505 · Cited by 42 · see citing works
Self-citationDer Weg zu nichtenzymatischen molekularen Netzwerken
Dadon, Z., Wagner, N., & Ashkenasy, G. (2008) · Angewandte Chemie · doi:10.1002/ange.200702552 · Cited by 35 · see citing works
Kinetic Insight into Specific Features of the Autocatalytic Soai Reaction
Lavabre, D., Micheau, J.-C., Islas, J. R., & Buhse, T. (2007) · Topics in Current Chemistry · doi:10.1007/128_2007_149 · Cited by 34 · see citing works
Self-citationOpen Prebiotic Environments Drive Emergent Phenomena and Complex Behavior
Wagner, N., Hochberg, D., Peacock-López, E., Maity, I., & Ashkenasy, G. (2019) · Life · doi:10.3390/life9020045 · Cited by 24 · see citing works
Byrne, L., Solà, J., & Clayden, J. (2015) · Chemical Communications · doi:10.1039/c5cc01790d · Cited by 14 · see citing works
Kinetic Analysis of Self-Replicating Peptides: Possibility of Chiral Amplification in Open Systems
Rivera-Islas, J., Micheau, J. C., & Buhse, T. (2004) · Origins of Life and Evolution of Biospheres · doi:10.1023/b:orig.0000043115.95561.23 · Cited by 13 · see citing works
Self-citationKinetic and Structural Aspects of Mirror-Image Symmetry Breaking in the Soai Reaction
Buhse, T., Noble‐Terán, M. E., Cruz, J., Micheau, J. C., & Coudret, C. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00004-6 · Cited by 4 · see citing works
Self-citationSelf‐Replication in Chemistry and Biology
Holliger, P., & Loakes, D. (2009) · Wiley eBooks · doi:10.1002/9780470437988.ch13
- Authors
- Rivera Islas, J., Pimienta, V., Micheau, J.-C., & Buhse, T.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Universidad Autónoma del Estado de Morelos (MX)
- Corresponding author
- Buhse, Thomas
- Venue
- Biophysical Chemistry
- Publisher
- Elsevier BV
- Published
- 2003-03
- Volume
- 103
- Issue
- 3
- Pages
- 201-211
- ISSN
- 0301-4622 (ISSN-L)
- OpenAlex
- W4250931849
- Cited by
- 15
- References
- 26
- Citations by year
- 2022: 1 · 2021: 1 · 2019: 1 · 2017: 1 · 2015: 1 · 2014: 1 · 2012: 1
- FWCI
- 0.19
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biophysical Chemistry (publishedVersion)
- Funders
- Consejo Nacional de Ciencia y Tecnología
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
- Keywords
- kinetic modeling, stereoselectivity, autocatalysis, cross-catalysis, enantiomeric excess amplification, chiral amplification
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review