Abstract
In 1990, Brown [1] described the present situation as follows: “Lack of appreciation (but not of knowledge) of the facts that stereoisomers are different compounds and that enantiomers often exert different biological effects has been one factor leading to failure to recognise the significance of chirality in assuring safety, quality and efficacy for medicinal products”. Public concern about chiral environmental pollutants can be stated at least since the “Thalidomide/Contergan® case” (see Sect. 4.1). However, adequate regulatory steps have only been taken so far for chiral drugs, while the application of chiral pesticides still needs corresponding regulations both at national and international levels. This lack of regulation seems to be world-wide and results in case-by-case judgments. A survey of the legal implications of chirality is given in several review papers and monographs [1–5]. With regard to the registration of chiral drugs, Witte et al. attempted an overview of the situation in three of the world’s most important pharmaceutical areas [4], the most important issues of which are as dealt with in the following sections.
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References
Brown JR (1990) Drug chirality. Impact on pharmaceutical regulation. Legal Studies and Services Limited, Healthcare & Regulatory Affairs Division, The London Press Centre, London, UK
Ariëns EJ (1993) Nonchiral, homochiral and composite chiral drugs. Trends Pharmacol Sci 14: 68–75
Landoni MF, Soraci AL, Delatour P, Lees P (1997) Enantioselective behaviour of drugs used in domestic animals: a review. J Vet Pharmacol Therap 20: 1–16
Witte DT, Kees E, Franke J-P, De Zeeuw RA (1993) Development and registration of chiral drugs. Pharmacy World & Science 15: 10–11
Hutt AJ (1991) Drug chirality: impact on pharmaceutical regulation. Chirality 3: 161164
Ariëns E (1986) Stereochemistry: a source of problems in medicinal chemistry. Med Res Rev 6: 451–466
Hoffmann F, Hühnerfuss H, Stine KJ (1998) Temperature dependence of chiral discrimination in monolayers of N-acylamino acids as inferred from 17/A measurements and infrared reflection-absorption spectroscopy. Langmuir 14: 4525–4534
Krempaskÿ J, Krejèíovâ E (1993) On the origin of “pure” chirality of amino acids and saccharides at the prebiotical stage. Gen Pysiol Biophys 12: 85–91
Schwartz AW (1994) The origin of macromolecular chirality. Curr Biol 4: 758–760
Bredig B, Mangold P, Williams TG (1923) Über “absolute” asymmetrische Synthese. Angew Chem 36: 456–458
Bailey J, Chrysostomou A, Hough JH, Gledhill TM, McCall A, Clark S, Ménard F, Tamura M (1998) Circular polarization in star-formation regions: implications for bio-molecular homochirality. Science 281: 672–674
Deutsch DH (1991) A mechanism for molecular asymmetry. J Mol Evol 33: 295–296
Bernstein WJ, Calvin M, Buchardt 0 (1972) Absolute asymmetric synthesis. I. On the mechanism of the photochemical synthesis of nonracemic helicenes with circularly polarized light. Wavelength dependence of the optical yield of octahelicene. J Am Chem Soc 94: 494–498
Bernstein WJ, Calvin M, Buchardt 0 (1973) Absolute asymmetric synthesis. III. Hindered rotation about aryl-ethylene bonds in the excited states of diaryl ethylenes. Structural effects on the asymmetric synthesis of 2- and 4-substituted hexahelicenes. J Am Chem Soc 95: 527–532
Kagan H, Moradpour A, Nicoud JF, Balavoine G, Martin RH, Cosyn JP (1971) Photochemistry with circularly polarised light. II. Asymmetric synthesis of octa-and nonahelicene. Tetrahedron Lett 1971: 2479–2482
Zadel G, Eisenbraun C, Wolff G-J, Breitmaier E (1994) Enantioselektive Reaktionen im statischen Magnetfeld. Angew Chem 106:460–463; Angew Chem Int Ed Eng1 33: 454
Feringa BL, Kellogg RM, Hulst R, Zondervan C, Kruizinga WH (1994) Attempts to carry out enantioselective reactions in a static magnetic field. Angew Chem 106: 15261527
Kaupp G, Marquardt T (1994) Absolute asymmetrische Synthese allein durch ein statisches Magnetfeld? Angew Chem 106: 1527–1529
Quack M (1989) Struktur and Dynamik chiraler Moleküle. Angew Chem 101: 588–604
Van House J, Rich A, Zitzewitz PW (1984) Beta decay and the origin of biological chirality: new experimental results. Origin of Life 14: 413–420
Podlech J (1999) Neue Einblicke in den Ursprung der Homochiralität biologisch relevanter Moleküle–Grundstoffe des Lebens aus dem All? Angew Chem 111:501–502; Angew Chem Int Ed 38: 477–478
Cronin JR, Pizzarello S (1997) Enantiomeric excesses in meteoritic amino acids. Science 275: 951–955
Flores JJ, Bonner WA, Massey GA (1977) Asymmetric photolysis of ( RS)-leucine with circularly polarised ultraviolet light. J Am Chem Soc 99: 3622–3625
Rubenstein E, Bonner WA, Noyes HP, Brown GS (1983) Supernovae and life. Nature 306: 118
Green MM, Selinger JV (1998) Cosmic chirality. Science 282: 880–881
Wittung P, Nielson PE, Buchardt O, Edholm M, Norden B (1994) DNA-like double helix formed by peptide nucleic acid. Nature: 368: 561–563
Kaupp G, Haak M (1993) Absolute Synthese durch Belichtung chiraler Kristalle. Angew Chem 105: 727–728
Ushio T, Tamura R, Takahashi H, Azuma N, Yamamoto K (1996) Ungewöhnliche Phänomene bei der Racematspaltung durch Umkristallisation einer racemischen Verbindung. Angew Chem 108: 2544–2546
Hanein D, Geiger B, Addadi L (1994) Differential adhesion of cells to enantiomorphous crystal surfaces. Science 263: 1413–1416
Neumann V, Gericke A, Hühnerfuss H (1995) Comparison of enantiomeric and racemic monolayers of 2-hydroxyhexadecanoic acid by external infrared reflection-absorption spectroscopy. Langmuir 11: 2206–2212
Hühnerfuss H, Neumann V, Stine KJ (1996) The role of hydrogen bond and metal complex formation for chiral discrimination in amino acid monolayers studied by infrared reflection-absorption spectroscopy. Langmuir 12: 2561–2569
Hühnerfuss H, Gericke A, Neumann V, Stine KJ (1996) The determination of the molecular order of chiral monolayers at the air/water interface by infrared reflection-absorption spectroscopy “IRRAS”–a bridge between physico-and biochemistry. Thin Solid Films 284: 694–697
Hoffmann F, Hühnerfuss H, Stine KJ (1998) Temperature dependence of chiral discrimination in monolayers of N-acyl amino acids as inferred from 17/A-measurements and infrared reflection-absorption spectroscopy. Langmuir 14: 4525–4534
Gericke A, Hühnerfuss H (1994) Infrared spectroscopic comparison of enantiomeric and racemic N-octadecanoylserine methyl ester monolayers at the air/water interface. Langmuir 10: 3782–3786
Stine KJ, Uang JY-J, Dingman SD (1993) Comparison of enantiomeric and racemic monolayers of N-stearoylserine methyl ester by fluorescence microscopy. Langmuir 9: 2112–2118
Stine KJ, Whitt SA, Uang JY-J (1994) Fluorescence microscopy study of Langmuir monolayers of racemic and enantiomeric N-stearoyltyrosine. Chem Phys Lipids 69: 4150
Parazak DP, Uang JY-J, Turner B, Stine KJ (1994) Fluorescence microscopy study of chiral discrimination in Langmuir monolayers of N-acylvaline and -alanine amphiphiles. Langmuir 10:3787-
Bringezu F, Brezesinski G, Nuhn P, Möhwald H (1996) Chiral discrimination in a mono-layer of a triple-chain phosphatidylcholine. Biophys J 70: 1789–1795
Groves JT, McConnell HM (1996) Chiral discrimination in two dimensions. Biophys J 70: 1573–1574
Bodenhöfer K, Hierlemann, Seemann J, Gauglitz G, Koppenhoefer B, Göpel W (1997) Chiral discrimination using piezoelectric and optical gas sensors. Nature 387: 577–580
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Kallenborn, R., Hühnerfuss, H. (2001). Perspectives of Enantioselective Analyses. In: Chiral Environmental Pollutants. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-06243-2_5
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DOI: https://doi.org/10.1007/978-3-662-06243-2_5
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-08569-7
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