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Thesis for Printing Chemistry of Hydroxycinnamate Esters and their Role as Precursors to Dekkera Produced Off-flavour in Wine A thesis presented in fulfilment of the requirements for the degree of Doctor of Philosophy Josh L. Hixson BTech (Forens&AnalytChem), BSc (Hons) School of Agriculture, Food and Wine March 2012 Table of Contents Abstract ................................................................................................................................ iv Declaration ......................................................................................................................... vii Acknowledgements ........................................................................................................... viii Publications and Symposia ................................................................................................ xi Abbreviations .................................................................................................................... xiii Figures, Schemes and Tables ........................................................................................... xvi Chapter 1: Introduction ...................................................................................................... 1 1.1 General Introduction ........................................................................................................ 1 1.2 Dekkera/Brettanomyces bruxellensis ............................................................................... 1 1.3 Volatile Phenols ............................................................................................................... 5 1.3 Introduction to Tartrate Esters ....................................................................................... 11 1.4 Introduction to Glucose Esters ....................................................................................... 16 1.5 Introduction to Ethyl Esters ........................................................................................... 18 1.5 Research Aims ............................................................................................................... 20 Chapter 2: Synthesis of Hydroxycinnamoyl Esters ........................................................ 22 2.1 Synthesis of Hydroxycinnamic Acids and Derivatives ................................................. 22 2.2 Synthesis of Hydroxycinnamoyl Tartrate Esters ........................................................... 24 2.2.1 Introduction to Tartrate Ester Synthesis ............................................................. 24 2.2.2 Synthesis of Hydroxycinnamoyl Tartrate Esters ................................................ 26 2.3 Synthesis of Hydroxycinnamoyl Glucose Esters ........................................................... 34 2.3.1 Introduction to Glucose Ester Synthesis ............................................................. 34 2.3.2 Synthesis of Hydroxycinnamoyl Glucose Esters ................................................ 37 2.4 Conclusions .................................................................................................................... 47 i Chapter 3: Acyl Migration of Hydroxycinnamoyl Glucose Esters ............................... 50 3.1 Introduction. ................................................................................................................... 50 3.2 Research Aims ............................................................................................................... 54 3.3 Theoretical Studies into Acyl Migration of Hydroxycinnamoyl Glucoses ................... 55 3.3.1 Thermodynamics of Migration ........................................................................... 55 3.3.2 Kinetics of Migration .......................................................................................... 60 3.4 Liquid Chromatography of Wine. .................................................................................. 67 3.5 Conclusions. ................................................................................................................... 76 Chapter 4: Photoisomerisation of Hydroxycinnamic Acids .......................................... 79 4.1 Introduction. ................................................................................................................... 79 4.1.1 Hydroxycinnamate Photoisomerisation .............................................................. 79 4.1.2 cis -Hydroxycinnamate content in grapes and wine ............................................ 81 4.1.3 Enzymatic Specificity ......................................................................................... 83 4.2 Research Aims ............................................................................................................... 86 4.3 Synthesis of cis -Hydroxycinnamic Acids. ..................................................................... 87 4.4 Theoretical Studies into the Isomerisation of Hydroxycinnamic Acids ........................ 91 4.5 Conclusions .................................................................................................................. 105 Chapter 5: Bioconversion of Hydroxycinnamates by D. bruxellensis ......................... 107 5.1 Bioconversion of trans -Hydroxycinnamate Esters ...................................................... 107 5.1.1 Ethyl Esters ....................................................................................................... 107 5.1.2 Ethyl Esterase Substrate Selectivity ................................................................. 110 5.1.3 Tartrate Esters ................................................................................................... 111 5.1.4 Glucose Esters ................................................................................................... 113 5.1.5 Conclusions for Chapter 5.1 ............................................................................. 114 5.2 Stereoselectivity of D. bruxellensis Enzyme Activities ............................................... 115 5.2.1 Decarboxylase Stereoselectivity ....................................................................... 115 ii 5.2.2 Ethyl Esterase Stereoselectivity ........................................................................ 121 5.2.3 Conclusions for Chapter 5.2 ............................................................................. 125 5.3 Thesis Conclusions and Future Directions .................................................................. 126 Chapter 6: Experimental ................................................................................................. 130 6.1 General Experimental .................................................................................................. 130 6.2 Experimental Procedures for Chapter 2 ....................................................................... 133 6.2.1 Hydroxycinnamoyl Derivatives ........................................................................ 133 6.2.2 Synthesis of Hydroxycinnamoyl Tartrate Esters .............................................. 142 6.2.3 Synthesis of Hydroxycinnamoyl Glucose Esters .............................................. 157 6.3 Experimental Procedures for Chapter 3 ....................................................................... 172 6.4 Experimental Procedures for Chapter 4 ....................................................................... 175 6.5 Experimental Procedures for Chapter 5 ....................................................................... 180 6.5.1 General Procedures for Chapter 5 ..................................................................... 180 6.5.2 Fermentation of trans -Hydroxycinnamate Esters ............................................. 184 6.5.3 Stereoselectivity of D. bruxellensis Enzyme Activities .................................... 184 Appendix 1: Data for Migration Thermodynamics ...................................................... 186 Appendix 2: Data for Migration Kinetics ...................................................................... 188 Appendix 3: Data for Energy Profiles ............................................................................ 190 Appendix 4: Data for Vertical Excitations and HOMO-LUMO Gaps ....................... 192 Appendix 5: Data from Ethylphenol Analyses .............................................................. 196 References ......................................................................................................................... 198 iii Abstract The potential for malodour in wine caused by the accumulation of ethylphenols has been widely studied with respect to the breakdown of the hydroxycinnamic acids, p-coumaric and ferulic acid, by D. bruxellensis . The presence of esterified hydroxycinnamate conjugates in grapes and wine is well established and they account for a large proportion of the hydroxycinnamate content. There exists the possibility that these conjugates could also provide the potential for spoilage, though they have never been linked to the direct formation of ethylphenols. The research highlighted within this thesis examines the potential role of a number of esterified conjugates in the production of ethylphenols by D. bruxellensis . Two classes of berry derived esters, the tartaric acid and glucose bound hydroxycinnamates, as well as the vinification formed ethyl esters, were synthesised and used for model fermentation experiments. Chapter 2 describes the preparation of a number of protected hydroxycinnamic acid
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