article

Chirality known and unknown (part one)

Jaromír Literák

information

volume: 32
year: 2023
issue: 4
fulltext: PDF

online publishing date: 13/3/2024
DOI: 10.14712/25337556.2023.4.3
ISSN (Online): 2533-7556

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abstract

The existence of an object, non-superimposable on its mirror image, constitutes the phenomenon of chirality. This phenomenon is often treated as a curiosity without broader practical consequences. This paper aims to show the significant implications of chirality for chemistry and biology. Chirality is inherent to all living organisms and is essential for their functioning. For instance, biomolecules are composed of chiral building blocks (amino acids, monosaccharides), which are chiral and occur predominantly with one sense of handedness (homochirality of life). The explanation of the evolution of the homochirality of life is therefore one of the important questions connected with the origin of life. The paper also shows why asymmetry with respect to mirror reflection is a general attribute of our world. Historical milestones in the scientific reflection on chirality are also presented, starting with the French crystallographers of the late 18th century, through the work of Pasteur, the fundamentals of organic stereochemistry postulated by van 't Hoff and Le Bel, the elucidation of a structure of monosaccharides by Fischer, and ending with the discovery of the absolute configuration of a molecule and the confirmation of parity violation of weak interaction.


keywords

chirality, homochirality of life, optical activity, history of stereochemistry

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References

Barron, L. D. (2008). Chirality and Life. Space Science Reviews, 135(2008), 187. https://doi.org/10.1007/s11214-007-9254-7

Barron, L. D. (2021). Symmetry and Chirality: Where Physics Shakes Hands with Chemistry and Biology. Israel Journal of Chemistry, 61(9-10), 517. https://doi.org/10.1002/ijch.202100044

Brown, A. H. (1993). Circumnutation: From Darwin to Space Flights. Plant Physiology, 101(2), 345. https://doi.org/10.1104/pp.101.2.345

Cintas, P. (2007). Tracing the Origins and Evolution of Chirality and Handness in Chemical Language. Angewandte Chemie, International Edition, 46(22), 4016. https://doi.org/10.1002/anie.200603714

Constable, E. C. (2021). Through a Glass Darkly – Some Thoughts on Symmetry and Chemistry. Symmetry, 13(10), 1891. https://doi.org/10.3390/sym13101891

Da Camara, C. A. G. (2021). Construction of a Low-Cost Polarimeter for Educational Purposes. Química Nova, 44(3), 361. https://doi.org/10.21577/0100-4042.20170661

Eliel, E. L., Wilen, S. H., & Mander, L. N. (1994). Stereochemistry of Organic Compounds. Hoboken: Wiley.

Gal, J. (2013). Molecular Chirality in Chemistry and Biology: Historical Milestones. Helvetica Chimica Acta, 96(9), 1617. https://doi.org/10.1002/hlca.201300300

Gal, J. (2019). Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids. Helv. Chim. Acta, 102(3), 1. https://doi.org/10.1002/hlca.201800226

Grossman, R. B. (1989). Van't Hoff, Le Bel, and the Development of Stereochemistry: A Reassessment. Journal of Chemical Education, 66(1), 30. https://doi.org/10.1021/ed066p30

Hashimoto, T. (2002). Molecular genetic analysis of left-right handness in plants. Philosophical Transactions of the Royal Society B: Biological Sciences, 357(1422), 799. https://doi.org/10.1098/rstb.2002.1088

Inaki, M., Liu, J., & Matsuno, K. (2016). Cell chirality: its origin and roles in left-right asymmetric development. Philosophical Transactions of the Royal Society B: Biological Sciences, 371(1710), 1. https://doi.org/10.1098/rstb.2015.0403

Katsoprinakis, G. E., & Rakitzis, T. P. (2019). Cavity-based chiral polarimetry: parity nonconserving optical rotation in Cs, Dy, and HgH. Journal of Physics B: Atomic, Molecular and Optical Physics, 52(21), 213501. https://doi.org/10.1088/1361-6455/ab410b

Lichtenthaler, F. W. (2002). Emil Fischer, His Personality, His Achievements, and His Scientific Progeny. European Journal of Organic Chemistry, 2002(24), 4095. https://doi.org/10.1002/1099-0690(200212)2002:24<4095::AID-EJOC4095>3.0.CO;2-2

McBryde, W. A. E. (1987). J. H. van't Hoff. Journal of Chemical Education, 64(7), 573. https://doi.org/10.1021/ed064p573

Quack, M. (2002). How Important is Parity Violation for Molecular and Biomolecular Chirality? Angewandte Chemie, International Edition, 41(24), 4618. https://doi.org/10.1002/anie.200290005

Schilthuizen, M., & Davison, A. (2005). The convoluted evolution of snail chirality. Naturwissenschaften, 92(11), 504. https://doi.org/10.1007/s00114-05-0045-2

Suh, I.-H., Park, K. H., Jensen, W. P., & Lewis, D. E. (1997). Molecules, Crystals, and Chirality. Journal of Chemical Education, 74(7), 800. https://doi.org/10.1021/ed074p800

Tobe, Y. (2003). The reexamination of Pasteur's experiment in Japan. Mendeleev Communications, 13(3), 93. https://doi.org/10.1070/MC2003v013n03ABEH001803

Vantomme, G., & Crassous, J. (2021). Pasteur and chirality: A story of how serendipity favors the prepared minds. Chirality, 33(10), 597. https://doi.org/10.1002/chir.23349

What is Chirality (2017, červenec 4) In ChemistryViews, The Magazine of Chemistry Europe. https://doi.org/10.1002/chemv.201700044


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