The nose as a stereochemist. Enantiomers and odor

Chemical Reviews

Volumn 106, Issue 9, 2006, Pages 4099-4112

  Bentley, Ronald ^a,b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS; ENANTIOSELECTIVITY; NOSE;

NITROGEN COMPOUNDS; ODORS; STEREOCHEMISTRY; SULFUR COMPOUNDS;

SENSORY PERCEPTION;

AMINE; PYRAZINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFUR DERIVATIVE;

CHEMISTRY; CONFORMATION; DRUG EFFECT; HUMAN; NOSE; ODOR; PHYSIOLOGY; REVIEW; STEREOISOMERISM;

AMINES; HUMANS; MOLECULAR CONFORMATION; NOSE; ODORS; PYRAZINES; PYRROLIDINES; SMELL; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 33749863296     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr050049t     Document Type: Review

References (109)

1. McManus, C. Right Hand, Left Hand. The Origins of Asymmetry in Brains, Bodies, Atoms and Cultures; Weidenfeld & Nicolson: London,2002.
2. Bentley, R. In Encyclopedia of Molecular Cell Biology and Molecular Medicine; Meyers, R. A., Ed; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, p 579.
3. Tadros, S. F.; Frisina, S. T.; Mapes, F.; Kim, S.; Frisina, D. R. Audiol. Neuro-Otol. 2005, 10, 44.
4. Sim, T. C.; Martinez, C. Laterality 2005, 10, 149.
5. Greenstein, J. P.; Winitz, M. Chemistry of the Amino Acids; Wiley & Sons: New York, 1961; Vol. 3, p 1860.
6. Morris, C., Ed. Academic Press Dictionary of Science and Technology; Academic Press: San Diego, CA 1992; p 1502.
7. Weyerstahl, P. J. Prakt. Chem., Chem.-Z 1994, 336, 95.
8. Theimer, E, T.; Yoshida, T.; Klaiber, E. M. J. Agric. Food Chem. 1977, 25, 1168.
9. Bernreuther, A.; Epperlein, U.; Koppenhoefer, B.; In Techniques for Analyzing Food Aroma; Marsili, R., Ed.; Dekker: New York, 1997; p 143.
10. Ohloff, G. Scent and Fragrances. The Fascination of Odors and their Chemical Perspectives; Springer-Verlag: Berlin, 1994.
11. Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Angew. Chem., Int. Ed. 2000, 39, 2980.
12. Ohloff, G. Helv. Chim. Acta 1992, 75, 1341, 2041.
13. Brenna, E.; Fugant, C.; Serra, S. Tetrahedron: Asymmetry 2003, 14, 1.
14. Abate, A.; Brenna, E.; Fugant, C.; Gatti, F. G.; Serra, S. Chem. Biodiversity 2004, 1, 1888.
15. Sell, C. S. Chem. Biodiversity 2004, 1, 1899.
16. Leffingwell, J. C. http://www.lefingwell.com/chirality/chirality.htm. Accessed 4/25/2005.
17. Pfaffmann, C. Encyclopedia Brittanica Online; http://search.eb.com/eb/ article 9109526.
18. Ache, B. W.; Young, J. M. Neuron 2005, 48, 417 and references therein.
19. Axel, R. Nobel Lecture in Physiology and Medicine, 2004. Angew. Chem., Int. Ed. 2005, 44, 6110.
20. Buck, L. B. Nobel Lecture in Physiology and Medicine, 2004. Angew. Chem., Int. Ed. 2005, 44, 6128.
21. Vosshall, L. B. Trends Neurosci. 2003, 26, 169.
22. Bentley, R. Molecular Asymmetry in Biology; Academic Press: New York, 1969: Vol. 1, p 222.
23. Pasteur, L. Alembic Club Reprint, No. 14; reissued by Livingstone: Edinburgh, 1948.
24. König, W. A.; Hochmuth, D. H. J. Chromatogr. Sci. 2004, 42, 423.
25. Bentley, R. Arch. Biochem. Biophys. 2003, 424, 1.
26. Demole, E.; Wuest, H. Helv. Chim. Acta 1967, 50, 1314.
27. Bruch, R. C.; Kalinoski, D. L.; Kare, M. R. Annu. Rev. Nutr. 1988, 8, 21.
28. Ma, M.; Shepherd, G. M. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 12869.
29. Messiha, A.; Leon, M. J. Neurosci. 2001, 21, 9937.
30. Rubin, B. D.; Katz, L. C. Nat. Neurosci. 2001, 4, 355.
31. Slotnick, B.; Bisulco, S. Neuroscience 2003, 121, 451.
32. Hamana, H.; Hirono, J.; Kizumi, M.; Sato, T. Chem. Senses 2003, 28, 87.
33. Reisemnan, C. E.; Christensen, T. A.; Francke, W.; Hildebrand, J. G. J. Neurosci. 2004, 24, 2602.
34. Kay, L. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 17569.
35. Turin, L. Chem. Senses 1996, 21, 773.
36. Turin, L. J. Theor. Biol. 2002, 216, 367.
37. Keller, A.; Vosshall, L. B. Nat. Neurosci. 2004, 7, 337.
38. Burr, C. The Emperor of Scent: A Story of Perfume, Obsession, and the Last Mystery of the Senses; Random House: New York, 2002.
39. Russell, G. F.; Hills, J. I. Science 1971, 172, 1043.
40. Leiteregg, T. J.; Guadagni, D. G.; Harris, J.; Mon, T. R.; Teranishi, R. Nature 1971, 230, 456;
41. Leiteregg, T. J.; Guadagni, D. G.; Harris, J.; Mon, T. R.; Teranishi, R. J. Agric. Food Chem. 1971, 19, 785.
42. Friedman, L.; Miller, J. G. Science 1971, 172, 1044.
43. Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 1346.
44. Wysocki, C. J.; Beauchamp, G. K. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 4899.
45. Wysocki, C. J.; Derries, K. M.; Beauchamp, G. K. Proc. Natl. Acad Sci. U.S.A. 1989, 86, 7976.
46. Case, T. I.; Stevenson, R. J.; Dempsey, R. A. Perception 2004, 33, 113.
47. Laska, M.; Teubner, P. Chem. Senses 1999, 24, 161.
48. Laska, M. Chem. Senses 2004, 29, 143.
49. Polak, E. H.; Fombon, A. M.; Tilquin, C.; Punter, P. H. Behav. Brain Res. 1989, 31, 199.
50. Pickenhagen, W.; Brönner-Schindler, H. Helv. Chim. Acta 1984, 67, 947.
51. Haring, H. G.; Rijkens, F.; Boelens, H.; van der Gen, A. J. Agric. Food Chem 1972, 20, 1018.
52. Kraft, P.; Fráter, G. Chirality 2001, 13, 388.
53. Demole, E.; Enggist, P.; Ohloff, G. Helv. Chim. Acta 1982, 65, 1785.
54. Lehmann, D.; Dietrich, A.; Hener, U.; Mosandl, A. Phytochem. Anal. 1995, 6, 255.
55. Giersch, W.; Farris, I. Helv. Chim. Acta 2004, 87, 1601.
56. Lüntzel, C. S.; Widder, S.; Vössing, T.; Pickenhagen, W. J. Agric. Food Chem. 2000, 48, 424.
57. Braun, N. A.; Meier, M.; Schmaus, G.; Hölscher, B.; Pickenhagen, W. Helv. Chim. Acta 2003, 86, 2698.
58. Guth, H. Heiv. Chim. Acta 1996, 79, 1559.
59. Guth, H. J. Agric. Food Chem. 1997, 45, 3022.
60. Mihara, G.; Masuda, H.; Nishimura, O.; Tateba, H. J. Agric. Food Chem. 1990, 38, 465.
61. Masuda, H.; Mihara, S. Agric. Biol. Chem. 1989, 53, 3367.
62. Tachihara, T.; Ishizaki, S.; Ishikawa, M.; Kitahara, T. Chem. Biodiversity 2004, 1, 2024.
63. Tachihara, T.; Ishizaki, S.; Kurobayashi, Y.; Tamura, H.; Ikemoto, Y.; Onuma, A.; Yoshikawa, K.; Yanai, T.; Kitahara, T. Helv. Chim Acta 2003, 86, 274.
64. Jameson, S. B. In Chemistry and Technology of Flavors and Fragrances; Rowe, D. J., Ed.; Blackwell: Oxford, U.K., 2005, p116.
65. Goeke, A. Sulfur Rep. 2002, 23, 243.
66. Werkhoff, P.; Güntert, M.; Krammer, G.; Sommer. H.; Kaulen, J. J. Agric. Food Chem. 1998, 46, 1076.
67. Van der Waal, M.; Niclass, Y.; Snowden, R. L.; Bernardinelli, G.; Escher, S. Helv. Chim. Acta 2002, 85, 1246.
68. Heusinger, G.; Mosandl, A. Tetrahedron Lett. 1984, 25, 507.
69. Weber, B.; Maas, B.; Mosandl, A. J. Agric. Food Chem. 1995, 43, 2438.
70. Mosandl, A.; Heusinger, G. Liebigs Ann. Chem. 1985, 1185.
71. Singer, G.; Heusinger, G.; Fröhlich, O.; Schreier, P.; Mosandl. A. J. Agric. Food Chem. 1986, 34, 1029.
72. Bentley, R. Chem. Soc. Rev. 2005, 34, 609.
73. Mosandl, A.; Deger, W.; Gessner, M.; Günther, C.; Heusinger, G.; Singer, G. Lebensmittelchem. Gerichtl. Chem. 1987, 41, 35.
74. Bentley, R.; Meganathan, R. FEBS Lett. 1981, 125, 220 and references therein.
75. Darriel, P.; Lamy, S.; La Guerche, S.; Pons, M.; Dubourdieu, D.; Balncard, D., Steliopoulos, P.; Mosandl, A. Eur. Food Res. Technol. 2001, 213, 122.
76. Ômura, H.; Kawahara, Y.; Tanabe, T. J. Chem. Ecol. 2002, 28, 2601.
77. Polak, E. H.; Provasi, J. Chem. Senses 1992, 17, 23.
78. Lu, G.; Edwards, C. G.; Fellman, J. K.; Mattinson, D. S.; Navazio, J. J. Agric. Food Chem. 2003, 51, 1026.
79. www.afchemicals.com/products/geosmin-dpg.html. Accessed 5/20/2005.
80. Huber, U.; Boland, W.; König, W. A.; Gehrcke, B. Helv. Chim. Acta 1993, 76, 1949.
81. Rieck, A.; Bülow, N.; König, W. A. Phytochemistry 1995, 40, 847.
82. Kimer, A.; Deutsch, S.; Weiler, E.; Polak, E. H.; Apfelbach, R. Behav. Brain Res. 2003, 138, 201,
83. Lehnikuhle, M.; Normann, R.; Maynard, E. Chem. Senses 2003, 28, 499.
84. Laska, M.; Liesen, A.; Teubner, P. Am. J. Physiol. 1999, 277, R1098.
85. Brand, J. G.; Bryant, B. P.; Cagan, R. H.; Kalinoski, D. L. Brain Res. 1987, 416, 119.
86. Alifimoff, J. K.; Bugge, B.; Forman, S. A.; Miller, K. W. Anesthesiology 1993, 79, 122.
87. Lipschitz, D. L.; Michel, W. C. J. Neurophysiol. 1999, 82, 3160.
88. Rolen, S. H.; Sorensen, P. W., Mattson, D.; Caprio, J. J. Exp. Biol, 2003, 206, 1683.
89. Fuss, S. H.; Korsching, S. I. J. Neurosci. 2001, 21, 8396.
90. Nikonov, A. A.; Caprio, J. J. Neurophysiol. 2001, 86, 1869.
91. Laska, M.; Galizia, C. G.; Giurfa, M.; Menzel, R. Chem. Senses 1999, 24, 429.
92. Laska, M.; Galizia, C. G. Behav. Neurosci. 2001, 115, 632.
93. Mori, K. Chirality 1998, 10, 578.
94. Eisner, T. For Love of Insects; Belknap Press of Harvard University Press: Cambridge, MA, 2003.
95. Stranden, M.; Borg-Karlson, A.-K.; Mustaparta, H. Chem. Senses 2002, 27, 143.
96. Wibe, A.; Borg-Karlson, A.-K.; Persson, M.; Norin, T.; Mustaparta, H. J. Chem. Ecol. 1998, 24, 273.
97. Hull, C. D.; Cunningham, J. P.; Moore, C. J.; Zalucki, M. P.; Cribb, B. W. J. Chem. Ecol. 2004, 30, 2071.
98. Mosandl, A. J. Chromatogr. Sci. 2004, 42, 440.
99. Kreis, P.; Mosandl, A. Flavour Fragrance J. 1992, 7, 187.
100. Steffen, A.; Pawliszyn, J. J. Agric. Food Chem. 1996, 44, 2187.
101. Ruiz del Castillo, M. L.; Caja, M. M.; Herraiz, M. J. Agric. Food Chem. 2003, 51, 1284.
102. Siano, F.; Catalfamo, M.; Cantela, D.; Servillo, L.; Castaldo, D. Food Addit. Contam. 2005, 22, 197.
103. Demirci, B.; Tabanca, N.; Başer, K. H. C. Flavour Fragrance J. 2002, 17, 54.
104. Wüst, M.; Reindl, J.; Fuchs, S.; Beek, T.; Mosandl, A. J. Agric. Food Chem. 1999, 47, 3145.
105. Culp, R. A.; Noakes, J. E. J. Agric. Food Chem. 1992, 40, 1892.
106. Hör, K.; Ruff, C.; Weckerle, B.; König, T.; Schreier, P. J. Agric. Food Chem. 2001, 49, 21.
107. Bilke, S.; Mosandl, A. Eur. Food Res. Technol. 2002, 214, 532.
108. Sewenig, S.; Bullinger, D.; Hener, U.; Mosandl, A. J. Agric. Food Chem. 2005, 53, 838.
109. Sybilska, D.; Asztemborska, M. J. Biochem. Biophys. Methods 2002, 54, 187.