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From Optical Activity in Quartz to Chiral Drugs: Molecular Handedness in Biology and Medicine

1995/12/01 by Ronald Bentley · 1 citation
Chemistry · #Analytical Chemistry and Chromatography #Molecular spectroscopy and chirality #Chemistry and Stereochemistry Studies

paper · doi:10.1353/pbm.1995.0069

openalex publication_date 1995/12/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/15

Abstract

From Optical Activity in Quartz to Chiral Drugs:Molecular Handedness in Biology and Medicine Ronald Bentley, Professor Emeritus Ronald Bentley, Professor Emeritus Department of Biological Sciences, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 References 1. BROWNE, M. W. "Mirror image" chemistry yielding new products. The New York Times, 13 Aug. 1991, sect. B: 5, 8. Google Scholar 2. FDA's policy statement for the development of new stereoisomeric drugs. Chirality 4:338-340, 1992. Google Scholar 3. FEDER, B. J. Separating "mirror" molecules for better drugs. The New York Times, 12 Feb. 1992, sect. C: 7. Google Scholar 4. LEWIN, R. Chemistry in the image of biology. Science 238:611-612, 1987. Google Scholar 5. CHAIKEN, I.; CHIANCONE, E.; FONTANA, A.; and NERI, P., eds. Macromolecular Biorecognition: Principles and Methods. Clifton, N.J.: Humana Press, 1987. Google Scholar 6. ROBERTS, S. M., ed. Molecular Recognition: Chemical and Biochemical Problems. Vols. I, II. Cambridge: Royal Society of Chemistry, 1989, 1992. Google Scholar 7. HOLMSTEDT, B.; FRANK, H.; and TESTA, B., eds. Chirality and Biological Activity. New York: A. R. Liss, 1990. Google Scholar 8. BROWN, C., ed. Chirality in Drug Design and Synthesis. San Diego: Academic Press, 1991. Google Scholar 9. WILSON, K., and WALKER, J. Chirality and its importance in drug development. Biochem. Soc. Trans. 19:443-474, 1991. Google Scholar 10. SHELDON, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds. New York: M. Dekker, 1993. Google Scholar 11. AMATO, I. Looking glass chemistry. Science 256:964-966, 1992. Google Scholar 12. CAHN, R. S.; INGOLD, C.; and PRELOG, V. Specification of molecular chirality. Angew. Chem. Internat. Edit. 5:385-415, 1966. Google Scholar 13. MISLOW, K. Introduction to Stereochemistry. New York: W. A. Benjamin, 1965. Google Scholar 14. BIELLMANN, J.-F. Chiralité du diptérocarpol en C-20. Tetrahedron Letters, 4803-4805, 1966. Google Scholar 15. MACDERMOTT, A. J. Distinguishing true chirality from its accidental imitators. Nature 323:16-17, 1986. Google Scholar 16. BARRON, L. D. True and false chirality and absolute asymmetric synthesis. J. Amer. Chem. Soc. 108:5539-5542, 1986. Google Scholar 17. KYBA, E. P.; SIEGEL, M. G.; SOUSA, L. R.; et al. Chiral, hinged, and functionalized multiheteromacrocycles. J. Amer. Chem. Soc. 95:2691-2692, 1973. Google Scholar 18. KYBA, E. P.; KOGA, K.; SOUSA, L. R.; et al. Chiral recognition in molecular complexing. J. Amer. Chem. Soc. 95:2692-2693, 1973. Google Scholar 19. JOB, R., and BRUICE, T. C. Chiral recognition of a prochiral (meso-carbon) centre by Λ(—)436-α-l,l-2,9-diamino-4,7-diazadecanecobaltate. J. Chem. Soc. Chem. Comm. 332-333, 1973. Google Scholar 20. HERSCHEL, J. F. W. On the rotation impressed by plates of rock crystal on the planes of polarization of the rays of light, as connected with certain peculiarities in its crystallization. Trans. Camb. Phil. Soc. 1:43-52, 1822. Google Scholar 21. PASTEUR, L. Researches on the Molecular Asymmetry of Natural Organic Products. Reissue edition published for the Alembic Club. Edinburgh: E. & S. Livingstone, 1948. Google Scholar 22. JAPP, F. R. Stereochemistry and vitalism. Nature 58:452-460, 1898. Google Scholar 23. HANEIN, D.; GEIGER, B.; and ADDADI, L. Differential adhesion of cells to enantiomorphous crystal surfaces. Science 263:1413-1416, 1994. Google Scholar 24. FRANKLAND, P. Pasteur Memorial Lecture. J. Chem. Soc. Trans. 71:683-743, 1897. Google Scholar 25. FISCHER, E. Ueber die Spaltung einiger racemischer Amidosäuren in die optisch-activen Componenten. Ber. dtsch. chem. Ges. 32:2451-2471, 1899. Google Scholar 26. FISCHER, E. Synthesen in der Zuckergruppe. Ber. dtsch. chem. Ges. 23:2114-2141, 1890. Google Scholar 27. FISCHER, E. Einfluss der Configuration auf die Wirkung der Enzyme. Ber. dtsch. chem. Ges. 27:2985-2993, 1894. Google Scholar 28. FISCHER, E., and BERGELL, P. Ueber die Derivate einiger Dipeptide und ihr Verhalten gegen Pankreasfermente. Ber. dtsch. chem. Ges. 33:2592-2608, 1903. Google Scholar 29. DAKIN, H. D. The hydrolysis of optically inactive esters...

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