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Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol. Qiang Tan Louisiana State University and Agricultural & Mechanical College

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Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol. Qiang Tan Louisiana State University and Agricultural & Mechanical College Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1996 Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol. Qiang Tan Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Tan, Qiang, "Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol." (1996). LSU Historical Dissertations and Theses. 6312. https://digitalcommons.lsu.edu/gradschool_disstheses/6312 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand comer and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book. Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6” x 9” black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. UMI A Bell & Howell Information Company 300 North Zeeb Road, Ann Arbor MI 48106-1346 USA 313/761-4700 800/521-0600 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. IMMOBILIZATION OF P.DIGITATUM AND BIOCONVERSION OF LIMONENE TO ALPHA-TERPINEOL A Dissertation Summitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Food Science by Qiang Tan B.S.. Southwest Agricultural University, P. R. China. 1984 M.S. Louisiana State University. Baton Rouge. 1992 December. 1996 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number: 9712860 UMI Microform 9712860 Copyright 1997, by UMI Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. UMI 300 North Zeeb Road Ann Arbor, MI 48103 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGMENT The author wishes to express his sincere and deepest appreciation to his present advisor, Dr. D. Day, for his continued support throughout the project his insightful advice as well as his encouragement and patience throughout the years. Appreciation is also extended to his former advisor, Dr. Keith R. Cadwallader, for his help in initiating this research topic and tremendous technical support during his tenure in the Food Science Department. Appreciation is expressed to Dr. Auttis Mullins, former Head, and Dr. Douglas L. Park, current Head, Department of Food Science, for their support of this research. Appreciation is extended to the Audubon Sugar Institute for providing the facilities and chemicals to conduct this research. Sincere thanks are given to Drs. Robert M. Grodner, Paul W. Wilson, Joseph A. Liuzzo, and E. William Wischusen (Dean’s Representative) for serving on the dissertation committee and for their valuable assistance and advice. The author would like to thank his lab colleges, Ms. D. Sarka, Mr. M. Ott. Mr. Sunkyun Yoo, Dr. Hau Yin Chung, and Ms. Narumol Thongwai for valuable discussions. Finally the author dedicates this work to his wife, Yu Yang, his daughter Jacqueline S. Tan and his families. Their encouragement, love, patience and understanding have made this work possible. ii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS ACKNOWLEDGMENT...................................................................................................... ii LIST OF TABLES............................................................................................................... vi LIST OF FIGURES............................................................................................................. vii ABSTRACT.......................................................................................................................... x INTRODUCTION.................................................................................................................. 1 REVIEW OF LITERATURE............................................................................................... 3 I. Terpenes and terpinoids ................................................................................ 3 1. Background ............................................................................................... 3 2. Classification ............................................................................................. 4 3. Industrial uses of terpenes ........................................................................ 7 4. Monoterpenes ............................................................................................ 7 5. Limonene ................................................................................................ 10 6. a-Terpineol ............................................................................................. 11 II. Microbial bioconversion of monoterpenes ............................................... 12 1. Definition of bioconversion or biotransformation ............................... 12 2. Methods for bioconversion ................................................................... 13 3. Bacterial and fungal bioconversion of monoterpenes ......................... 15 IE. Microbial systems for hydroxylation reactions ......................................... 27 1. Microbiological hydroxylations ............................................................ 27 2. Microbial hydroxylation of aliphatic and aromatic compounds 27 3. Microbial hydroxylation of terpinoids .................................................. 30 4. Enzymatic systems and mechanisms related to microbial hydroxylation ......................................................................... 31 5. Stereochemistry of microbial hydroxylation ........................................ 39 IV. Fungal immobilization ................................................................................ 41 V. Whole-cell bioconversions in aqueous-organic solvent systems 44 1. Use of organic solvents in whole-cell biotransformations .................. 44 2. Solvent selection for whole cell biotransformations ........................... 45 3. Biotransformations on aqueous two-phase systems ............................ 49 VI. This study..................................................................................................... 51 MATERIALS AND METHODS........................................................................................ 52 I. Chemicals..................................................................................................... 52 II. Organism and growth conditions .............................................................. 52 III. Growth and bioconversion activity ........................................................... 53 iil Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. IV. Analytical methods ...................................................................................... 54 V. Extraction recovery ...................................................................................... 56 VI. Substrate induction ....................................................................................... 57 VII. Enzyme inhibition ........................................................................................ 57 Vm. Determination of the Michaelis-Menten constant ..................................... 58 IX. Determination of product stereochemistry ................................................. 58 X. Immobilization of P.digitatum on calcium alginate .................................. 59 XI. Separation of the calcium alginate beads from cell m ass ......................... 60 XII. Calcium alginate beads storage stability .................................................... 60 Xm. Optimization of limonene bioconversion ................................................... 60 1. Aeration ..................................................................................................
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