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

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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  • An enantiomeric excess amplification process is needed to reach enantiopure organic compounds.

    “Thus, an ee amplification process is needed to reach enantiopure organic compounds (Scheme 1).11–20)”

    From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [16]

    The paper’s Abstract reports amplification from low-ee proline to a sugar intermediate at 96% ee and proposes this as a possible route to homochiral molecules. It does not say amplification is necessary to obtain enantiopure organic compounds, and 96% ee is not enantiopure. (LLM, conf=0.85)

    Experimental — accuracy not yet measured

  • The linkage between the induced small enantioenrichment and enantiopure compounds has remained a puzzle.

    “The linkage between the induced small enantioenrichment and the enantiopure compounds has thus remained a puzzle.11–20)”

    From Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules (2019) · cites this paper as [16]

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Research works printed but not linked: 46

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  46. Note added in proof (June 12, 2006): Since this manuscript was accepted for publication, a paper by Blackmond and co-workers has appeared that describes a similar phenomenon (M. Kluss- mann, H. Iwamura, S. P. Mathew, D. H. Wells, Jr., U. Pandya, A. Armstrong, D. G. Blackmond, Nature 2006, 441, 621). The results in our present Communication explain the greater stability of crystals of dl-proline over those of the separate enantiomers and provide a rationale for the nonlinear effects observed in the ee of proline in solution and hence in the aldol reaction.

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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
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
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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