Cited by 120Origins and Evolution of LifeAsymmetric Synthesis and CatalysisChemistry and Stereochemistry Studies

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Large Nonlinear Effect Observed in the Enantiomeric Excess of Proline in Solution and That in the Solid State

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Hayashi, Yujiro, Matsuzawa, Masayoshi, Yamaguchi, Junichiro, Yonehara, Sayaka, Matsumoto, Yasunobu, Shoji, Mitsuru, Hashizume, Daisuke, Koshino, Hiroyuki·2006·Angewandte Chemie International Edition

DOI 10.1002/anie.200601506

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Abstract

A clue to the origin of chirality? A solution of proline with high enantiomeric excess (85–99 % ee) was obtained from solid proline of only 10 % ee through novel dissolution and crystallization processes (see scheme). This observation may be an explanation for the origin of chirality on Earth.

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Purification of Laboratory Chemicals
(2003) · Elsevier eBooks · doi:10.1016/b978-0-7506-7571-0.x5000-5 · Cited by 8,726
Purification of Laboratory Chemicals
Eaborn, C. (1989) · Journal of Organometallic Chemistry · doi:10.1016/0022-328x(89)85446-4 · Cited by 4,353
Proline-Catalyzed Direct Asymmetric Aldol Reactions
List, B., Lerner, R. A., & Barbas, C. F. (2000) · Journal of the American Chemical Society · doi:10.1021/ja994280y · Cited by 2,926
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Dalko, P. I., & Moisan, L. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200400650 · Cited by 2,599
Enantiomers, Racemates, and Resolutions
Jacques, J., Collet, A., & Wilen, S. H. (1981) · Cited by 1,714
Asymmetric Organocatalysis
Berkessel, A., & Gröger, H. (2005) · Wiley eBooks · doi:10.1002/3527604677 · Cited by 1,351
Amino Acid Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon−Carbon Bond-Forming Reactions
Sakthivel, K., Notz, W., Bui, T., & Barbas, C. F. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010037z · Cited by 1,167
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
New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures
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Amino acids from ultraviolet irradiation of interstellar ice analogues
Muñoz, G. M., Meierhenrich, U. J., Schutte, W. A., Barbier, B., Arcones, A., Rosenbauer, H., Thiemann, W., Brack, A., & Greenberg, J. M. (2002) · Nature · doi:10.1038/416403a · Cited by 850

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Kayushina R. L., 1965, Kristallografiya, 10, 834

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Authors: Hayashi, Y., Matsuzawa, M., Yamaguchi, J., Yonehara, S., Matsumoto, Y., Shoji, M., Hashizume, D., & Koshino, H.
Affiliations: Tokyo University of Science (JP)
RIKEN (JP)
ORCID: Hayashi, Yujiro
Yamaguchi, Junichiro
Shoji, Mitsuru
Hashizume, Daisuke
Koshino, Hiroyuki
Venue: Angewandte Chemie International Edition
Publisher: Wiley
Published: 2006-07-03
Volume: 45
Issue: 28
Pages: 4593-4597
ISSN: 1433-7851 (ISSN-L)
1521-3773
DOI: 10.1002/anie.200601506
OpenAlex: W2148937565
Cited by: 120
References: 68
Citations by year: 2025: 1 · 2022: 9 · 2021: 4 · 2020: 3 · 2019: 6 · 2018: 7 · 2017: 3 · 2016: 3 · 2015: 7 · 2014: 4 · 2013: 3 · 2012: 7
FWCI: 8.24
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations: Angewandte Chemie International Edition (publishedVersion)
PubMed (publishedVersion)
Funders: Ministry of Education, Culture, Sports, Science and Technology
University of Tokyo
Toray Science Foundation
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 › Chemistry and Stereochemistry Studies
Keywords: proline, enantiomeric excess, nonlinear optical effects, circular dichroism, enantiomeric excess amplification, amino acids
MeSH terms: Proline, Solutions, Time Factors, Molecular Structure

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Large Nonlinear Effect Observed in the Enantiomeric Excess of Proline in Solution and That in the Solid State

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