Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light
Open accessAbstract
Circularly polarized light (CPL) emitted from star-forming regions is an attractive candidate as a cause of single chirality in nature. It has remained difficult, however, to translate the relatively small chemical effects observed on irradiation of molecular systems with CPL into high enantiomeric excesses. Here we demonstrate that irradiation of a racemic amino acid derivative with CPL leads to a small amount of chiral induction that can be amplified readily to give an enantiopure solid phase. A racemate composed of equal amounts of left- and right-handed crystals in contact with the irradiated solution is converted completely into crystals of single-handedness through abrasive grinding when racemization is effected in the solution. The rotation sense of the CPL fully determines the handedness of the final solid state. These findings illustrate the potential effectiveness of CPL in the control of molecular asymmetry, which is relevant for the origin of the single chirality inherent to many biological molecules.
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In 2009, Vlieg et al. coupled CPL with Viedma ripening to achieve complete and deterministic mirror-symmetry breaking.
“In 2009, Vlieg et al. coupled CPL with Viedma ripening to achieve complete and deterministic mirror-symmetry breaking.419”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [419]
CPL-controlled complete attrition-enhanced deracemization of rac-1 occurs.
“CPL-controlled complete attrition-enhanced deracemization of rac-1.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [419]
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“Recently, Viedma's technique was extended by some of us to intrinsically chiral molecules that crystallize as separate left- and right-handed crystals to form a racemic conglomerate in the solid phas”
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Symmetry Breaking in Self-Assembled Nanoassemblies
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“description, it can be concluded that a non-racemizable chiral photoproduct may be formed under the effect of the CPL irradiation, while the subsequent grind treatment amplified the small initial chirality [146].”
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- Authors
- Noorduin, W. L., Bode, A. A. C., van der Meijden, M., Meekes, H., van Etteger, A. F., van Enckevort, W. J. P., Christianen, P. C. M., Kaptein, B., Kellogg, R. M., Rasing, T., & Vlieg, E.
- Affiliations
- Radboud University Nijmegen (NL)
- DSM (Netherlands) (NL)
- Corresponding author
- Vlieg, Elias
- Venue
- Nature Chemistry
- Published
- 2009-11-01
- Volume
- 1
- Issue
- 9
- Pages
- 729-732
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- OpenAlex
- W2128295433
- Cited by
- 247
- References
- 7
- Citations by year
- 2026: 8 · 2025: 13 · 2024: 14 · 2023: 15 · 2022: 21 · 2021: 16 · 2020: 18 · 2019: 22 · 2018: 12 · 2017: 14 · 2016: 14 · 2015: 11 · 2014: 13 · 2013: 13 · 2012: 24
- FWCI
- 7.23
- Type
- journal article
- Language
- en
- Open access
- green
- research.rug.nl
- Licence
- other-oa
- www.springer.com/tdm (tdm)
- Locations
- Nature Chemistry (publishedVersion)
- PubMed (publishedVersion)
- University of Groningen research database (University of Groningen / Centre for Information Technology) (submittedVersion, other-oa)
- Radboud Repository (Radboud University) (submittedVersion)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Keywords
- circularly polarized light, chiral induction, chiral symmetry breaking, amino acid derivatives, enantiomeric excess, origin of homochirality, racemic crystals, abrasive grinding, racemization, handedness control, circular dichroism
- MeSH terms
- Amino Acids, Chromatography, High Pressure Liquid, Circular Dichroism, Light, Solutions, Spectrophotometry, Ultraviolet, Stereoisomerism, Time Factors, Bridged Bicyclo Compounds, Heterocyclic
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