Mechanism of wine lactone formation: Demonstration of stereoselective cyclization and 1,3-hydride shift

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 26, 2006, Pages 10245-10252

  Luan, Fang ^a   Degenhardt, Andreas ^a   Mosandl, Armin ^a   Wüst, Matthias ^b  

^a GOETHE UNIVERSITY   (Germany)

^b University of Applied Sciences Valais   (Switzerland)

Author keywords

1,3 hydride shift; Deuterium labeling; Enantioselective gas chromatography; Flavor; Ion trap tandem mass spectrometry; Monoterpenes; Stereoselective cyclization; Wine lactone

Indexed keywords

DEUTERIUM; LACTONE;

ARTICLE; CYCLIZATION; ISOTOPE LABELING; MASS FRAGMENTOGRAPHY; STEREOISOMERISM; SYNTHESIS; WINE;

CYCLIZATION; DEUTERIUM; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ISOTOPE LABELING; LACTONES; STEREOISOMERISM; WINE;

EID: 33846476293     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0625306     Document Type: Article

References (31)

1. Wüst, M.; Mosandl, A. Important chiral monoterpenoid ethers in flavours and essential oils - Enantioselective analysis and biogenesis. Eur. Food Res. Technol. 1999, 209 (1), 3-11.
2. Serra, S.; Fuganti, C.; Brenna, E. Biocatalytic preparation of natural flavours and fragrances. Trends Biotechnol. 2005, 23 (4), 193-198.
3. Winterhalter, P.; Bonnländer, B. Aroma-active benzofuran derivatives: Analysis, sensory properties, and pathways of formation. ACS Symp. Ser. 2001, 794, 21-32.
4. Guth, H. Determination of the configuration of wine lactone. Helv. Chim. Acta 1996, 79 (6), 1559-1571.
5. Guth, H. Identification of character impact odorants of different white wine varieties. J. Agric. Food Chem. 1997, 45 (8), 3022-3026.
6. Guth, H. Quantitation and sensory studies of character impact odorants of different white wine varieties. J. Agric. Food Chem. 1997, 45 (8), 3027-3032.
7. Jagella, T.; Grosch, W. Flavour and off-flavour compounds of black and white pepper (Piper nigrum L.) I. Evaluation of potent odorants of black pepper by dilution and concentration techniques. Eur. Food Res. Technol. 1999, 209 (1), 16-21.
8. Fuhrmann, E.; Grosch, W. Character impact odorants of the apple cultivars Elstar and Cox Orange. Nahrung-Food 2002, 46 (3), 187-193.
9. Buettner, A.; Schieberle, P. Evaluation of aroma differences between hand-squeezed juices from valencia late and navel oranges by quantitation of key odorants and flavor reconstitution experiments. J. Agric. Food Chem. 2001, 49 (5), 2387-2394.
10. Buettner, A.; Schieberle, P. Characterization of the most odoractive volatiles in fresh, hand-squeezed juice of grapefruit (Citrus parodisi Macfayden). J. Agric. Food Chem. 1999, 47 (12), 5189-5193.
11. Hognadottir, A.; Rouseff, R. L. Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry. J. Chromatogr. A 2003, 998 (1-2.), 201-211.
12. Lopez, R.; Ferreira, V.; Hernandez, P.; Cacho, J. F. Identification of impact odorants of young red wines made with Merlot, Cabernet Sauvignon and Grenache grape varieties: A comparative study. J. Sci. Food Agric. 1999, 79 (11), 1461-1467.
13. Grosch, W. Evaluation of the key odorants of foods by dilution experiments, aroma models and omission. Chem. Senses 2001, 26 (5), 533-545.
14. Bonnländer, B.; Baderschneider, B.; Messerer, M.; Winterhalter, P. Isolation of two novel terpenoid glucose esters from Riesling wine. J. Agric. Food Chem. 1998, 46 (4), 1474-1478.
15. Winterhalter, P.; Messerer, M.; Bonnländer, B. Isolation of the glucose ester of (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid from Riesling wine. Vitis 1997, 36 (1), 55-56.
16. Bonnländer, B. Isolierung, Charakterisierung und Synthese von Aromavorläufern aus Wein, Dillkraut und Lindenblüten. Ph.D. Thesis, Technische Universität Braunschweig, Braunschweig, Germany, 2002.
17. Christianson, D. W. Structural biology and chemistry of the terpenoid cyclases. Chem. Rev. 2006, 106, 3412-3442.
18. Whittington, D. A.; Wise, M. L.; Urbansky, M.; Coates, R. M.; Croteau, R. B.; Christianson, D. W. Bornyl diphosphate synthase: Structure and strategy for carbocation manipulation by a terpenoid cyclase. Proc. Natl. Acad. Sci. U.S.A. 2002, 99 (24), 15375-80.
19. Greenhagen, B.; Chappell, J. Molecular scaffolds for chemical wizardry: Learning nature's rules for terpene cyclases. Proc. Natl. Acad. Sci. U.S.A. 2001, 98 (24), 13479-81.
20. Croteau, R. B.; Shaskus, J. J.; Renstrom, B.; Felton, N. M.; Cane, D. E.; Saito, A.; Chang, C. Mechanism of the pyrophosphate migration in the enzymatic cyclization of geranyl and linalyl pyrophosphates to (+)- and (-)-bornyl pyrophosphates. Biochemistry 1985, 24 (25), 7077-85.
21. Cuvigny, T.; Julia, M.; Rolando, M. Stereoselective gamma-cis-vinylic metallation of tertiary alcohols. Chem. Commun. 1984, 8.
22. Hiraga, Y.; Izumi, S.; Hirata, T.; Suga, T. Facile Synthesis of Regioselectively Deuteriated (3R)-(-)-[8,8,8-(H-2)3]Linalool. Chem. Lett. 1991, (1), 49-52.
23. Chaintreau, A. Simultaneous distillation-extraction: From birth to maturity - A review. Flavour Fragrance J. 2001, 16 (2), 136-148.
24. Guth, H. Objectification of white wine aromas. Habilitationschrift, Technical University, Munich, Germany, 1997.
25. Wüst, M.; Fuchs, S.; Rexroth, A.; Beck, T.; Mosandl, A. Fragmentation mechanism of rose oxide in electron impact mass spectrometry. Eur. Mass Spectrom. 1998, 4 (3), 163-166.
26. Starks, C. M.; Back, K.; Chappell, J.; Noel, J. P. Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science 1997, 277 (5333), 1815-20.
27. Godtfredsen, S.; Obrecht, J. P.; Arigoni, D. Cyclization of Linalool to Alpha-Terpineol - Stereochemical Course of Reaction. Chimia 1977, 31 (2), 62-63.
28. Poulter, C. D.; King, C. H. R. Model Studies of Terpene Biosynthesis - Stereospecific Cyclization of N-Methyl-(S)-4-([1′-H-2]Neryloxy)Pyridinium Methyl Sulfate to α-Terpineol. J. Am. Chem. Soc. 1982, 104 (5), 1420-1422.
29. Poulter, C. D.; King, C. H. R. Model Studies of Terpene Biosynthesis - A Stepwise Mechanism for Cyclization of Nerol to α-Terpineol. J. Am. Chem. Soc. 1982, 104 (5), 1422-1424.
30. Moruno, E. G. The chirality of alpha-terpineol in aromatic wines. Detection of chiral or racemic linalool addition in wines. Sci. Aliments 1999, 19 (2), 207-214.
31. Luan, F.; Hampel, D.; Mosandl, A.; Wüst, M. Enantioselective analysis of free and glycosidically bound monoterpene polyols in Vitis vinifera L. Cvs. Morio Muscat and Muscat Ottonel: Evidence for an oxidative monoterpene metabolism in grapes. J. Agric. Food Chem. 2004, 52 (7), 2036-2041.