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Review
. 2015 Jun 11;20(6):10781-92.
doi: 10.3390/molecules200610781.

Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes

Henry B Wedler  1 , Ryan P Pemberton  2 , Dean J Tantillo  3
Affiliations
Review

Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes

Henry B Wedler et al. Molecules. .

Abstract

Computational chemistry approaches for studying the formation of terpenes/terpenoids in wines are presented, using five particular terpenes/terpenoids (1,8-cineole, α-ylangene, botrydial, rotundone, and the wine lactone), volatile compounds (or their precursors) found in wine and/or wine grapes, as representative examples. Through these examples, we show how modern computational quantum chemistry can be employed as an effective tool for assessing the validity of proposed mechanisms for terpene/terpenoid formation.

Keywords: aroma; biosynthesis; mechanism; quantum chemistry; terpene; wine.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Overview of chemical transformations in terpene biosynthesis.
Scheme 1
Scheme 1
1,8-Cineole-forming carbocation cascade.
Scheme 2
Scheme 2
α-Ylangene-forming carbocation cascade.
Scheme 3
Scheme 3
Presilphiperfolanol-forming carbocation cascade.
Scheme 4
Scheme 4
Proposed biosynthetic formation of rotundone: α-guaiene-forming carbocation cascade followed by radical-initiated oxidation.
Scheme 5
Scheme 5
Proposed mechanism for formation of the wine lactone.
See this image and copyright information in PMC

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