Cited by 28Asymmetric Synthesis and CatalysisOrigins and Evolution of LifeCrystallization and Solubility Studies

Achiral amino acid glycine acts as an origin of homochirality in asymmetric autocatalysis

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Matsumoto, Arimasa, Ozaki, Hanae, Tsuchiya, Sumeru, Asahi, Toru, Lahav, Meir, Kawasaki, Tsuneomi, Soai, Kenso·2019·Organic & Biomolecular Chemistry

Abstract

Achiral glycine acts as the origin of chirality in conjunction with asymmetric autocatalysis to afford highly enantioenriched compound.

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Crossref · 10.1039/c9ob00345b

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56 of 56 references verified0 citation errors · 0 not checkable

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  • Enantio-enriched or enantiopure pyrimidine alcohol was generated with determined configuration when the autocatalytic Soai reaction was initiated with chiral crystals such as quartz, gamma-glycine, cinnabar, anhydrous cytosine, triglycine sulfate, or with enantiotopic faces of achiral crystals such as gypsum.

    “Enantio-enriched or enantiopure pyrimidine alcohol was generated with determined configuration when the auto-catalytic reaction was initiated with chiral crystals, such as (a)-quartz, 406 g-glycine, 407 N-(2-thienylcarbonyl)glycine, 408 cinnabar, 409 anhydrous cytosine, 292 or triglycine sulfate, 410 or with enantiotopic faces of achiral crystals such as CaSO 4 Á2H 2 O (gypsum).411”

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Authors
Matsumoto, A., Ozaki, H., Tsuchiya, S., Asahi, T., Lahav, M., Kawasaki, T., & Soai, K.
Affiliations
  • Tokyo University of Science (JP)
  • Waseda University (JP)
  • Weizmann Institute of Science (IL)
Corresponding author
Soai, Kenso
Venue
Organic & Biomolecular Chemistry
Published
2019
Volume
17
Issue
17
Pages
4200-4203
ISSN
  • 1477-0520 (ISSN-L)
  • 1477-0539
OpenAlex
W2934370561
Cited by
28
References
56
Citations by year
2026: 2 · 2025: 1 · 2024: 3 · 2023: 7 · 2022: 6 · 2021: 7 · 2019: 2
FWCI
1.47
Type
journal article
Language
en
Open access
Locations
  • Organic & Biomolecular Chemistry (publishedVersion, cc-by-nc)
  • PubMed (publishedVersion)
Funders
  • Japan Society for the Promotion of Science (15H03781)
  • Ministry of Education, Culture, Sports, Science and Technology (S1201005)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Physical Sciences › Materials Science › Materials Chemistry › Crystallization and Solubility Studies
Keywords
glycine, homochirality, asymmetric autocatalysis, enantiomeric excess amplification, chiral crystals, γ-glycine, circular dichroism, Cotton effect, origin of homochirality

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