Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality
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Achiral meteoritic amino acids, glycine and alpha-methylalanine, with hydrogen isotope (D/H) chirality, acted as the source of chirality in asymmetric autocatalysis with amplification of ee to afford highly enantioenriched 5-pyrimidyl alkanols.
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Chiral isotopomers of glycine-α-d 12 used as chiral triggers in the reaction of i-Pr2Zn with pyrimidine-5-carbaldehyde 2c gave alkanol 1c with high ee.
“Chiral isotopomers of glycine-α-d 12 were used as chiral triggers in an asymmetric autocatalysis in the reaction between i-Pr2Zn and pyrimidine-5-carbaldehyde 2c to afford alkanol 1c with high ee.101)”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [101]
The absolute configuration of the produced alkanol 1c was controlled by the chirality of the trigger from hydrogen isotope substitution.
“The absolute configuration of the produced alkanol 1c was controlled by the chirality of the trigger resulting from hydrogen isotope substitution.”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [101]
Using (R)-glycine-α-d 12 as trigger gave the opposite (R)-1c.
“By contrast, in the presence of (R)-glycine-α-d 12, the opposite (R)-1c was formed.”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [101]
Using (S)-glycine-α-d 12 as trigger gave (S)-pyrimidyl alkanol 1c with high ee.
“When i-Pr2Zn was reacted with aldehyde 2c using a chiral trigger of (S)-glycine-α-d 12, (S)-pyrimidyl alkanol 1c with high ee was formed.”
From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [101]
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Deuterium‐ and Tritium‐Labelled Compounds: Applications in the Life Sciences
Atzrodt, J., Derdau, V., Kerr, W. J., & Reid, M. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201704146 · Cited by 808 · see citing works
Bissette, A. J., & Fletcher, S. P. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201303822 · Cited by 403 · 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
Soai, K., Kawasaki, T., & Matsumoto, A. (2014) · Accounts of Chemical Research · doi:10.1021/ar5003208 · Cited by 181 · see citing works
Self-citationDeuterium‐ und tritiummarkierte Verbindungen: Anwendungen in den modernen Biowissenschaften
Atzrodt, J., Derdau, V., Kerr, W. J., & Reid, M. (2017) · Angewandte Chemie · doi:10.1002/ange.201704146 · Cited by 117 · see citing works
Ercolani, G., & Schiaffino, L. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo102525t · Cited by 86 · see citing works
The Origins of Homochirality Examined by Using Asymmetric Autocatalysis
Soai, K., Kawasaki, T., & Matsumoto, A. (2014) · The Chemical Record · doi:10.1002/tcr.201300028 · Cited by 90 · see citing works
Self-citationAsymmetric 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
Self-citationMatsumoto, A., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201508036 · Cited by 75 · see citing works
Self-citationBissette, A. J., & Fletcher, S. P. (2013) · Angewandte Chemie · doi:10.1002/ange.201303822 · Cited by 71 · see citing works
Xia, A., Xu, D., Luo, S., Jiang, J., Tang, J., Wang, Y., & Xu, Z. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200902540 · Cited by 70 · see citing works
Stochastic aspects of asymmetric autocatalysis and absolute asymmetric synthesis
Barabás, B., Tóth, J., & Pályi, G. (2010) · Journal of Mathematical Chemistry · doi:10.1007/s10910-010-9680-8 · Cited by 67 · see citing works
Energy threshold for chiral symmetry breaking in molecular self-replication
Hawbaker, N. A., & Blackmond, D. G. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0321-y · Cited by 65 · see citing works
Kawasaki, T., & Soai, K. (2011) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20110120 · Cited by 65 · see citing works
Self-citationSOAI, K. (2019) · Proceedings of the Japan Academy Series B · doi:10.2183/pjab.95.009 · Cited by 63 · see citing works
Self-citationIn Situ Mass Spectrometric and Kinetic Investigations of Soai's Asymmetric Autocatalysis
Trapp, O., Lamour, S., Maier, F., Siegle, A. F., Zawatzky, K., & Straub, B. F. (2020) · Chemistry - A European Journal · doi:10.1002/chem.202003260 · Cited by 60 · see citing works
The Role of Stochastic Models in Interpreting the Origins of Biological Chirality
Lente, G. (2010) · Symmetry · doi:10.3390/sym2020767 · Cited by 58 · see citing works
Matsumoto, A., Ozaki, H., Harada, S., Tada, K., Ayugase, T., Ozawa, H., Kawasaki, T., & Soai, K. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201608955 · Cited by 53 · see citing works
Self-citationMechanism of the Asymmetric Autocatalytic Soai Reaction Studied by Density Functional Theory
Schiaffino, L., & Ercolani, G. (2010) · Chemistry - A European Journal · doi:10.1002/chem.200902543 · Cited by 50 · see citing works
Mills, M. D., Sonstrom, R. E., Vang, Z. P., Neill, J. L., Scolati, H. N., West, C. D., Pate, B. H., & Clark, J. R. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202207275 · Cited by 48 · see citing works
Matsumoto, A., Kaimori, Y., Uchida, M., Omori, H., Kawasaki, T., & Soai, K. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201610099 · Cited by 46 · see citing works
Self-citationSuzuki, K., Hatase, K., Nishiyama, D., Kawasaki, T., & Soai, K. (2010) · Journal of Systems Chemistry · doi:10.1186/1759-2208-1-5 · Cited by 46 · see citing works
Self-citationAmino Acid Ligand Chirality for Enantioselective Syntheses
Micskei, K., Patonay, T., Caglioti, L., & Pályi, G. (2010) · Chemistry & Biodiversity · doi:10.1002/cbdv.200900325 · Cited by 46 · see citing works
Soai, K., Kawasaki, T., & Matsumoto, A. (2018) · Tetrahedron · doi:10.1016/j.tet.2018.02.040 · Cited by 47 · see citing works
Self-citationKawasaki, T., Ozawa, H., Ito, M., & Soai, K. (2011) · Chemistry Letters · doi:10.1246/cl.2011.320 · Cited by 45 · see citing works
Self-citationAsymmetric autocatalysis triggered by oxygen isotopically chiral glycerin
Matsumoto, A., Oji, S., Takano, S., Tada, K., Kawasaki, T., & Soai, K. (2013) · Organic & Biomolecular Chemistry · doi:10.1039/c3ob40293b · Cited by 45 · see citing works
Self-citationKawasaki, T., & Soai, K. (2012) · Israel Journal of Chemistry · doi:10.1002/ijch.201100155 · Cited by 44 · see citing works
Self-citationRole of Asymmetric Autocatalysis in the Elucidation of Origins of Homochirality of Organic Compounds
Soai, K., Kawasaki, T., & Matsumoto, A. (2019) · Symmetry · doi:10.3390/sym11050694 · Cited by 44 · see citing works
Self-citationHawbaker, N., & Blackmond, D. G. (2018) · ACS Central Science · doi:10.1021/acscentsci.8b00297 · Cited by 42 · see citing works
Amplification of chirality as a pathway to biological homochirality
Kawasaki, T., & Soai, K. (2009) · Journal of Fluorine Chemistry · doi:10.1016/j.jfluchem.2009.12.014 · Cited by 42 · see citing works
Self-citationSugahara, H., Meinert, C., Nahon, L., Jones, N. C., Hoffmann, S. V., Hamase, K., Takano, Y., & Meierhenrich, U. J. (2018) · Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics · doi:10.1016/j.bbapap.2018.01.004 · Cited by 38 · see citing works
Fletcher, S. P., Solà, J., Holt, D., Brown, R. A., & Clayden, J. (2011) · Beilstein Journal of Organic Chemistry · doi:10.3762/bjoc.7.152 · Cited by 32 · see citing works
Achiral amino acid glycine acts as an origin of homochirality in asymmetric autocatalysis
Matsumoto, A., Ozaki, H., Tsuchiya, S., Asahi, T., Lahav, M., Kawasaki, T., & Soai, K. (2019) · Organic & Biomolecular Chemistry · doi:10.1039/c9ob00345b · Cited by 28 · see citing works
Self-citationElucidation of the Structures of Asymmetric Autocatalyst Based on X-ray Crystallography
Matsumoto, A., Fujiwara, S., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K. (2016) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20160160 · Cited by 24 · see citing works
Self-citationOrigin of Chirality in the Molecules of Life
Cowan, J. A., & Furnstahl, R. J. (2022) · ACS Earth and Space Chemistry · doi:10.1021/acsearthspacechem.2c00032 · Cited by 24 · see citing works
Kawasaki, T., Sato, I., Mineki, H., Matsumoto, A., & Soai, K. (2013) · Journal of Synthetic Organic Chemistry Japan · doi:10.5059/yukigoseikyokaishi.71.109 · Cited by 23 · see citing works
Self-citationAsymmetric Autocatalysis of Pyrimidyl Alkanol
Soai, K., & Kawasaki, T. (2012) · Topics in organometallic chemistry · doi:10.1007/3418_2012_48 · Cited by 22 · see citing works
Self-citationOba, Y., Watanabe, N., Osamura, Y., & Kouchi, A. (2015) · Chemical Physics Letters · doi:10.1016/j.cplett.2015.05.070 · Cited by 21 · see citing works
Chiral rotational spectroscopy
Cameron, R. P., Götte, J. B., & Barnett, S. M. (2016) · Physical Review A · doi:10.1103/physreva.94.032505 · Cited by 19 · see citing works
Natural Abundance Isotopic Chirality in the Reagents of the Soai Reaction
Barabás, B., Kurdi, R., & Pályi, G. (2016) · Symmetry · doi:10.3390/sym8010002 · Cited by 18 · see citing works
Matsumoto, A., Abe, T., Hara, A., Tobita, T., Sasagawa, T., Kawasaki, T., & Soai, K. (2015) · Angewandte Chemie · doi:10.1002/ange.201508036 · Cited by 18 · see citing works
Self-citationSoai, K., Matsumoto, A., & Kawasaki, T. (2021) · Israel Journal of Chemistry · doi:10.1002/ijch.202100047 · Cited by 16 · see citing works
Self-citationAsymmetric 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 · doi:10.1002/ange.201102263 · Cited by 16 · see citing works
Self-citationXu, S., Oda, A., & Negishi, E. (2014) · Chemistry - A European Journal · doi:10.1002/chem.201405053 · Cited by 12 · see citing works
Isotope chirality in long‐armed multifunctional organosilicon (“<scp>Cephalopod</scp>”) molecules
Barabás, B., Kurdi, R., Zucchi, C., & Pályi, G. (2018) · Chirality · doi:10.1002/chir.22865 · Cited by 10 · see citing works
Pytlarczyk, M., Herman, J., Czerwiński, M., Arakawa, Y., Tsuji, H., & Kula, P. (2022) · Liquid Crystals · doi:10.1080/02678292.2022.2145379 · Cited by 10 · see citing works
Unidirectional Rotary Motion in Isotopically Chiral Molecular Motors: A Computational Analysis
Wang, J., Oruganti, B., & Durbeej, B. (2020) · Organic Letters · doi:10.1021/acs.orglett.0c02436 · Cited by 10 · see citing works
Soai, K., Kawasaki, T., & Matsumoto, A. (2022) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-022-09626-7 · Cited by 9 · see citing works
Self-citationAsymmetric Autocatalysis and the Origins of Homochirality of Organic Compounds. An Overview
Soai, K., Matsumoto, A., & Kawasaki, T. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00001-0 · Cited by 8 · see citing works
Self-citationMatsumoto, A., Kaimori, Y., Uchida, M., Omori, H., Kawasaki, T., & Soai, K. (2016) · Angewandte Chemie · doi:10.1002/ange.201610099 · Cited by 8 · see citing works
Self-citationHelical structures of homo-chiral isotope-labeled α-aminoisobutyric acid peptides
Ueda, A., Oba, M., Izumi, Y., Sueyoshi, Y., Doi, M., Demizu, Y., Kurihara, M., & Tanaka, M. (2016) · Tetrahedron · doi:10.1016/j.tet.2016.08.011 · Cited by 7 · see citing works
Asymmetric Autocatalysis and the Origin of Homochirality
Soai, K., & Matsumoto, A. (2017) · ACS symposium series · doi:10.1021/bk-2017-1258.ch003 · Cited by 6 · see citing works
Self-citationAsymmetric Induction by a Nitrogen 14N/15N Isotopomer in Conjunction with Asymmetric Autocatalysis
Matsumoto, A., Ozaki, H., Harada, S., Tada, K., Ayugase, T., Ozawa, H., Kawasaki, T., & Soai, K. (2016) · Angewandte Chemie · doi:10.1002/ange.201608955 · Cited by 6 · see citing works
Self-citationThe chirality of isotopomers of glycine compared using next‐generation QTAIM
Nie, X., Yang, Y., Xu, T., Biczysko, M., Kirk, S. R., & Jenkins, S. (2022) · International Journal of Quantum Chemistry · doi:10.1002/qua.26917 · Cited by 6 · see citing works
Quantitative Difference in Solubility of Diastereomeric (2H/1H)-Isotopomers
Kawasaki, T., Kubo, H., Nishiyama, S., Saijo, T., Yokoi, R., & Tokunaga, Y. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.1c09253 · Cited by 7 · see citing works
Self-citationAsymmetric Autocatalysis: The Soai Reaction, an Overview
Soai, K., Kawasaki, T., & Matsumoto, A. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00001 · Cited by 4 · see citing works
Self-citationChiral selectivity vs. noise in spontaneous mirror symmetry breaking
Hochberg, D., Buhse, T., Micheau, J. C., & Ribó, J. M. (2023) · Physical Chemistry Chemical Physics · doi:10.1039/d3cp03311b · Cited by 4 · see citing works
Kinetic 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
Robust and Scalable Synthesis of Soai Aldehydes via Improved Barbier‐type Halogen−lithium Exchange
Kenny, R., & Liu, F. (2022) · Asian Journal of Organic Chemistry · doi:10.1002/ajoc.202100787 · Cited by 3 · see citing works
Mills, M. D., Sonstrom, R. E., Vang, Z. P., Neill, J. L., Scolati, H. N., West, C. D., Pate, B. H., & Clark, J. R. (2022) · Angewandte Chemie · doi:10.1002/ange.202207275 · Cited by 2 · see citing works
Barabás, B., Kurdi, R., & Pályi, G. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00014-9 · Cited by 2 · see citing works
Kawasaki, T., Tateishi, D., Matsumoto, A., & Soai, K. (2024) · Tetrahedron · doi:10.1016/j.tet.2024.133835 · Cited by 2 · see citing works
Self-citationDirect determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
Wehrle, R. J., Powell, D. R., & Masterson, D. S. (2021) · Results in Chemistry · doi:10.1016/j.rechem.2021.100114 · Cited by 2 · see citing works
Structural Study of Asymmetric Autocatalysis by X-Ray Crystallography
Matsumoto, A., Kawasaki, T., & Soai, K. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00010-1 · Cited by 2 · see citing works
Self-citationAbsolute Asymmetric Synthesis in the Soai Reaction
Soai, K., Kawasaki, T., & Matsumoto, A. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00065 · Cited by 2 · see citing works
Self-citationModel Equivalency in Interpreting the Stochastic Enantiomer Distribution in the Soai Reaction
Lente, G. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812824-4.00009-5 · Cited by 1 · see citing works
Chiral Rotational Spectroscopy
Cameron, R. P., Götte, J. B., & Barnett, S. M. (2018) · Elsevier eBooks · doi:10.1016/b978-0-444-64027-7.00020-3 · Cited by 2 · see citing works
Lewerenz, H. (2011) · Springer series in optical sciences/SPringer series in optical sciences · doi:10.1007/978-3-642-23749-2_1
Kawasaki, T., Shimizu, M., Nishiyama, D., Ito, M. M. M., Ozawa, H., & Soai, K. (2009) · ChemInform · doi:10.1002/chin.200947027
Self-citationElucidating the Role of Isotopically Chiral Initiators in the Soai Asymmetric Autocatalytic ReactionPreprint
Hawbaker, N., & Blackmond, D. G. (2018) · ChemRxiv · doi:10.26434/chemrxiv.5787984.v1
(2019) · Elsevier eBooks · doi:10.1016/b978-0-12-812212-9.16001-4
(2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839163685-00104
Elucidation of Soai's Asymmetric Autocatalysis
Trapp, O. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00239
Kawasaki, T., Matsumoto, A., & Soai, K. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00033
Self-citationSpontaneous Emergence of Chirality in Autocatalytic Cycle Models of the Soai Reaction
Buhse, T., Noble‐Terán, M. E., Hochberg, D., Ribó, J. M., & Micheau, J. C. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00129
Matsumoto, A., Kawasaki, T., & Soai, K. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00273
Self-citationAsymmetric Autocatalysis Triggered by the Chirality of Minerals, Organic Crystals, and Surfaces
Matsumoto, A., Kawasaki, T., & Soai, K. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00043
Self-citationIsotope Chirality and Cosmochemistry
Barabás, B., Kurdi, R., Maioli, M., & Pályi, G. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00075
Stochastic Modeling of Asymmetric Autocatalysis in the Soai Reaction
Lente, G. (2022) · Royal Society of Chemistry eBooks · doi:10.1039/9781839166273-00179
A Continuing Career in Physical Organic Chemistry: Donna G. Blackmond
Ji, Y., Otte, D. A. L., & Ruck, R. T. (2023) · ACS Catalysis · doi:10.1021/acscatal.3c04565
Avnir, D. (2024) · Frontiers in Astronomy and Space Sciences · doi:10.3389/fspas.2024.1427260
Optical resolution of H/D isotopic chirality via asymmetric C–H amination
Uchida, T., Nakagawa, Y., Watari, N., & Kawasaki, Y. (2026) · Science Advances · doi:10.1126/sciadv.aed4187
- Authors
- Kawasaki, T., Shimizu, M., Nishiyama, D., Ito, M., Ozawa, H., & Soai, K.
- Affiliations
- Tokyo University of Science (JP)
- Corresponding author
- Soai, Kenso
- Venue
- Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2009
- Issue
- 29
- Pages
- 4396
- ISSN
- 1359-7345 (ISSN-L)
- 1364-548X
- PMC
- PMC2898652
- OpenAlex
- W2066137743
- Cited by
- 83
- References
- 70
- Citations by year
- 2026: 1 · 2024: 3 · 2023: 2 · 2022: 17 · 2021: 4 · 2020: 2 · 2019: 5 · 2018: 6 · 2017: 8 · 2016: 8 · 2015: 3 · 2014: 3 · 2013: 4 · 2012: 2
- FWCI
- 2.85
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- other-oa
- Locations
- Chemical Communications (publishedVersion, other-oa)
- Europe PMC (PubMed Central) (publishedVersion, cc-by-nc)
- PubMed Central (publishedVersion, cc-by-nc)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- asymmetric autocatalysis, meteoritic amino acids, glycine, deuterium, origin of homochirality, enantiomeric excess amplification, enantioenrichment
- MeSH terms
- Origin of Life, Amino Acids, Automation, Catalysis, Hydrogen, Stereoisomerism, Molecular Structure, Evolution, Molecular
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