Chirality timeline

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Chirality timeline presents a timeline of landmark events that unfold the developments happened in the field of chirality.

Many molecules come in two forms that are mirror images of each other, just like our hands. This type of molecule is called chiral. In nature, one of these forms is usually more common than the other. In our cells, one of these mirror images of a molecule fits "like a glove," while the other may be harmful.[1][2]

In nature, molecules with chirality include hormones, DNA, antibodies, and enzymes. For example, (R)-limonene smells like oranges, while (S)-limonene smells like lemons. Both molecules have the same chemical formula, but their spatial orientations are different, which makes a big difference in their biological properties. Chiral molecules in the receptors in our noses can tell the difference between these things. Chirality affects biochemical reactions, and the way a drug works depends on what kind of enantiomer it is. Many drugs are chiral and it is important that the shape of the drug matches the shape of the cell receptor it is meant to affect. Mismatching will make the drug less effective, which could be a matter of life and death, as happened with thalidomide in the 1960s.[3][4]

Pasteur and Molecular Asymmetry

It has long been known that structural factors, particularly chirality and stereochemistry, have a big impact on pharmacological efficacy and pharmacokinetic behavior. Since more than a century ago, pertinent information pertaining to chirality has been accumulating in numerous fields, in particular, physics, chemistry and biology, at an accelerated rate, giving rise to more comprehensive and in-depth reasoning, conceptions, and ideas.[5][6][7][8] This page offers a chronology of significant contributions that have been made in the journey of chirality [1809 to 2021].


Chirality timeline[edit]

Timeline of contributions in the field of chirality
Year Image Name Country Contribution/Achievement Ref
1809 Étienne-Louis Malus France Discovery of plane polarized light; Origin of stereochemistry [9]
1811 Dominique François Jean Arago France Showed how cut crystals change the plane of polarized light [10]
1812 Jean-Baptiste Biot France Found that a quartz plate cut at a right angle to its crystal axis rotates the plane of polarized light by an angle that is proportional to the thickness of the plate. This is the phenomenon of optical rotation [11]
1815 Jean-Baptiste Biot France Applied these ideas to organic substances, like oil of turpentine, sugar, camphor, and tartaric acid (solutions of solids) [12]
1820 Eilhard Mitscherlich German Discovery of the phenomenon of crystallographic isomorphism. Correlated the similarity of crystal shapes with an analogy in chemical composition, reported that sodium ammonium salts of (+)-tartaric acid and racemic acids are completely isomorphous and are identical in all aspects except in optical activity [13]
1848 Louis Pasteur France The racemic sodium ammonium salt of tartaric acid was crystallized, and two different types of crystals were found. First, enantiomers were physically separated [14]
1857 Louis Pasteur France Made the first observation of enantioselectivity in living things [15]
1874 Jacobus Henricus van't Hoff Netherlands Outlined the connection between a molecule's three-dimensional structure, its optical activity, and the idea of asymmetric carbon. Proposed a stereochemical theory of isomerism based on the three-dimensional structure of molecules. Van't Hoff, who won the first Nobel Prize in Chemistry in 1901, for discovery of the laws of chemical dynamics and osmotic pressure in solutions" [16]
1874 Joseph Achille Le Bel France Used asymmetry arguments and talked about the asymmetry of the molecules as a whole instead of the asymmetry of each carbon atom. Le Bel's thought could be considered as the general theory of stereoisomerism. [17]
1875 Jacobus Henricus van't Hoff Netherlands Predicted allenes' stereoisomerism, but it wasn't seen in the lab until 1935 [18]
1890 Hermann Emil Louis Fischer German Imagined the fit between the enzyme and the substrate as a lock and key mechanism. He made Fischer projections to show their three-dimensional structures. He was awarded the second Nobel Prize in chemistry, 1902 "in recognition of the extraordinary services he has rendered by his work on sugar and purine syntheses.". [19][20]
1890 Poulson Contributions to the knowledge of the pharmacological group of cocaine [21]
1894 Ehrlich  and Einhorn. Physiological and toxicological significance of chiral compounds; found (+)-cocaine was more active, started working faster, and lasted less time than (-)-cocaine. [22]
1903 Arthur Robertson Cushny United Kingdom Described how atropine and (-)-hyoscyamine work differently on the papillary, cardiac, and salivary systems and how they affect the spinal cord of a frog; First, gave clear examples of how the biological activity of two enantiomers of a chiral molecule can be different. [23]
1904 Pictet. and Rotschy Described the differences in nicotine isomers' toxic doses [24]
1904 William Thomson British The term "chiral" was first used and introduced. Later, Lord Kelvin was made a peer. [25]
1908 Abderhalden. and Müller Described (-)- and (+)-epinephrine have very different effects on blood pressure. [26]
1910 Grove Nicotine isomers have different levels of toxicity. [27]
1918 Frey Reported the isomer of quinine - quinidine, to be more effective in treating dysrhythmias. [28]
1933 Easson and Stedman Advanced a thee-point attachment model to explain chiral recognition process between the drug (with a single center of asymmetry) and the receptor or enzyme active site [29]
1957

1958

Lancelot Law Whyte Scotland Rediscovered term chiral ,[30][31]
1965 Kurt Martin Mislow United States Firmly reintroduced the term chirality into stereochemical  literature; German-born American organic chemist [32]
1956/1966 Robert Sidney Cahn British Devised  R/S and E/Z notations; Cahn–Ingold–Prelog priority rules [33]
1956/1966 Christopher Kelk Ingold British Co-author of Cahn–Ingold–Prelog priority rules; Did groundbreaking work (between 1920-30s) on reaction mechanisms and the electronic structure of organic compounds [33]
1956/1966 Vladimir Prelog Sarajevo Co-author of the Cahn–Ingold–Prelog priority rules [33]
1975 Vladimir Prelog Sarajevo Nobel prize in chemistry for his research into the stereochemistry of organic molecules and reaction [34]
1975 John Cornforth Australia Awarded Nobel prize for his work on the stereochemistry of enzyme-catalyzed reactions [35]
2001 William Standish Knowles United States Won Nobel prize in chemistry in 2001 for his work on the development of catalytic asymmetric synthesis (chirally catalyzed hydrogenation reactions [36]
2001 Ryōji Noyori Japan Won Nobel prize in chemistry in 2001 for his work on the development of catalytic asymmetric synthesis (chirally catalyzed hydrogenation reactions) [36]
2001 Karl Barry Sharpless United States Won Nobel prize in chemistry in 2001 for his work on the development of catalytic asymmetric synthesis (chirally catalyzed oxidation reactions) [36]
2021 Benjamin List German Awarded  Nobel Prize in Chemistry in 2021 for his work on the development of asymmetric organocatalysis [37]
2021 David MacMillan United Kingdom United States Awarded  Nobel Prize in Chemistry in 2021 for his work on the development of asymmetric organocatalysis [37]

See also[edit]

References[edit]

  1. ^ Crossley R (1992). "The relevance of chirality to the study of biological activity". Tetrahedron. 48 (38): 8155–8178. doi:10.1016/S0040-4020(01)80486-5.
  2. ^ "The Nobel Prize in Chemistry 2001". NobelPrize.org. Retrieved 2022-09-19.
  3. ^ Sheldon RA (1993). Chirotechnology : industrial synthesis of optically active compounds. New York: Marcel Dekker. ISBN 0-8247-9143-6. OCLC 27897833.
  4. ^ Browne MW (1991). "'Mirror Image' Chemistry Yielding New Products". The New York Times. pp. Section C, Page 1.
  5. ^ Busch KW, Marianna A, Busch MA (2006). Chiral Analysis. Elsevier. pp. 3–24. doi:10.1016/b978-0-444-51669-5.x5000-5. ISBN 978-0-444-51669-5.
  6. ^ Eliel EL (1994). Stereochemistry of organic compounds. Samuel H. Wilen, Lewis N. Mander. New York: Wiley. pp. 1–10. ISBN 0-471-01670-5. OCLC 27642721.
  7. ^ Smith SW (2009). "Chiral Toxicology: It's the Same Thing…Only Different". Toxicological Sciences. 110 (1): 4–30. doi:10.1093/toxsci/kfp097. ISSN 1096-6080. PMID 19414517.
  8. ^ Gal J (2013). "Molecular Chirality: Language, History, and Significance". In Schurig V (ed.). Differentiation of Enantiomers I. Topics in Current Chemistry. Vol. 340. Cham: Springer International Publishing. pp. 1–20. doi:10.1007/128_2013_435. ISBN 978-3-319-03238-2. PMID 23666078.
  9. ^ Malus EL (1809). "Sur une propriété de la lumière réfléchie" [On a property of reflected light.]. Mémoires de physique et de chimie de la Société d'Arcueil. (in French). 2: 143–158.
  10. ^ Arago F (1811). "Me´moire sur une modification remarquablequ'e´prouvent les rayons lumineux dans leur passage a' travers certains corps diaphanes, et sur quelquesautres nouveaux phe´nome'nesd'optique" [On an interesting effect shown by light rays on their passage through certain transparent materials and some other new optical phenomena]. Mém. Classe Sci. Math. Phys. Inst. Impérial France (in French). 1: 93–134.
  11. ^ Biot JB (1812). "Sur de nouveaux rapports qui existent entre la réflexion et la polarisation de la lumière des corps cristallisés" [On new relations which exist between the reflection and the polarization of the light of crystallized bodies.]. Mémoires de la classe des sciences mathématiques et physiques (in French). 13: 1.
  12. ^ Biot JB (1815). "Unknown". Bulletin de la Société philomathique de Paris: 190.
  13. ^ Mitscherlich E (1820). "Isomorphous Acid, Ostwald's Klassiker No. 94". Annales de Chimie et de Physique. 14: 172.
  14. ^ Pasteur L (1857). "Me´moire sur la fermentation alcoolique [Memoir on alcoholic fermentation]". Comptes rendus de l'Académie des Sciences. 45: 1032–1036.
  15. ^ Pasteur L (1857). "Me´moire sur la fermentation alcoolique" [Memoir on alcoholic fermentation]. Comptes rendus de l'Académie des Sciences (in French). 45: 1032–1036.
  16. ^ van't Hoff JH (1874). "Voorstel tot Uitbreiding der Tegenwoordige in de Scheikunde gebruikte Structuurformules in de Ruimte, benevens een daarmee samenhangende Opmerking omtrent het Verband tusschen Optisch Actief Vermogen en chemische Constitutie van Organische Verbindingen" [Proposal for the extension of current chemical structural formulas into space, together with related observation on the connection between optically active power and the chemical constitution of organic compounds.]. Archives Neerlandaises des Sciences Exactes et Naturelles (in Dutch). 9: 445–454.
  17. ^ Le Bel JA (1874). "Sur des relation qui existent entre les formules atomiques des corps organiques et le pouvoir rotatoire des leurs dissolutions" [On the relations which exist between the atomic formulas of organic compounds and the rotatory power of their solutions.]. Bulletin de la Société Chimique de France (in French). 22: 337–347.
  18. ^ van't Hoff JH (1875). La Chimie dans L'Espace [Chemistry in Space] (in French). Rotterdam, The Netherlands: P.M. Bazendijk. pp. 13–14.
  19. ^ Fischer E (1891). "Uber die Configuration des Traubenzuckers. und seiner Isomeren" [On the configuration of grape sugar and its isomers.]. Berichte der Deutschen Chemischen Gesellschaft (in German). 24: 1836–1845. doi:10.1002/cber.189102401311.
  20. ^ "The Nobel Prize in Chemistry 1902". NobelPrize.org. Retrieved 2022-09-25.
  21. ^ Poulson E (1890). "Beitra¨ge zur Kenntniss der pharmakologischen Gruppe des Cocains" [Contributions to the knowledge of the pharmacological group of cocaine.]. Berichte der Deutschen Chemischen Gesellschaft (in German). 27: 301–313. doi:10.1002/cber.189402702138.
  22. ^ Ehrlich P, Einhorn A (1894). "Ueber die physiologische Wirkung der Verbindungen der Cocaı¨nreihe" [About the physiological effect of the compounds of the cocaine series.]. Berichte der Deutschen Chemischen Gesellschaft (in German). 27 (2): 1870–1873. doi:10.1002/cber.189402702138.
  23. ^ Cushny AR (November 1903). "Atropine and the hyoscyamines-a study of the action of optical isomers". The Journal of Physiology. 30 (2): 176–194. doi:10.1113/jphysiol.1903.sp000988. PMC 1540678. PMID 16992694.
  24. ^ Pictet A, Rotschy A (March 1904). "Synthese des nicotins" [Synthesis of nicotine]. Berichte der Deutschen Chemischen Gesellschaft (in German). 37 (2): 1225–1235. doi:10.1002/cber.19040370206.
  25. ^ Kelvin LW (1904). Baltimore Lectures on Molecular Dynamics and the Wave Theory of Light. London: C. J. Clay & Sons. The lectures were given in 1884 and 1893.
  26. ^ Abderhalden E, Müller F. "Über das Verhalten des Blutdruckes nach intravenöser Einführung von l-, d-und dl-Suprarenin" [On the behavior of the blood pressure after intravenous administration of l-, d- and dl-suprarenin]. Hoppe-Seyler's Zeitschrift für Physiologische Chemie (in German). 58: 185–189. doi:10.1515/bchm2.1909.58.3.185.
  27. ^ Grove WE (1910). "On the toxicity of dextro-, laevo- and inactive camphor". Journal of Pharmacology and Experimental Therapeutics. 1: 445–456.
  28. ^ Frey W (1918). "Uber Vorhofflimern beim Menschen und seine Beseitigung durch Chiniden" [On atrial fibrillation in humans and its elimination by quiniods.]. Berliner Klinische Wochenschrift (in German). 55: 417–450, 450–452.
  29. ^ Easson LH, Stedman E (January 1933). "Studies on the relationship between chemical constitution and physiological action: Molecular dissymmetry and physiological activity". The Biochemical Journal. 27 (4): 1257–1266. doi:10.1042/bj0271257. PMC 1253018. PMID 16745220.
  30. ^ Whyte LL (1957). "Chirality". Nature. 180 (4584): 513. Bibcode:1957Natur.180..513W. doi:10.1038/180513b0. ISSN 0028-0836.
  31. ^ Whyte LL (1958). "Chirality". Nature. 182 (4629): 198. Bibcode:1958Natur.182..198W. doi:10.1038/182198a0. ISSN 0028-0836.
  32. ^ Mislow K (1965). Introduction to Stereochemistry. New York: Benjamin. p. 52. ISBN 978-1-62198-592-1.
  33. ^ a b c Cahn RS, Ingold C, Prelog V (1966). "Specification of Molecular Chirality". Angewandte Chemie International Edition in English. 5 (4): 385–415. doi:10.1002/anie.196603851. ISSN 0570-0833.
  34. ^ "The Nobel Prize in Chemistry 1975". NobelPrize.org. Retrieved 2022-09-15.
  35. ^ "The Nobel Prize in Chemistry 1975". NobelPrize.org. Retrieved 2022-09-15.
  36. ^ a b c "The Nobel Prize in Chemistry 2001". NobelPrize.org. Retrieved 2022-09-15.
  37. ^ a b "The Nobel Prize in Chemistry 2021". NobelPrize.org. Retrieved 2022-09-15.

External links[edit]

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