......................................................................................................................................... ii List of Figures ............................................................................................................................... ix List of Tables .............................................................................................................................. xiii List of Abbreviations ................................................................................................................. xiv Chapter 1 Dissertation Overview ................................................................................................ 1 Chapter 2 Literature Review ....................................................................................................... 3 2.1 Pullulan ............................................................................................................................ 3 2.1.1 Pullulan properties .................................................................................................... 4 2.1.2 Pullulan from A. pullulans ........................................................................................ 5 2.1.3 Commercial production of pullulan .......................................................................... 6 2.1.4 Pullulan biosynthesis ................................................................................................ 7 2.1.5 Food industry and pharmaceutical applications ........................................................ 8 2.1.6 Chemical modifications and biomedical applications .............................................. 9 2.2 Drug Delivery ................................................................................................................. 20 2.3 References ...................................................................................................................... 24 Chapter 3 Synthesis of Amphiphilic 6-Carboxypullulan Ethers ............................................ 30 3.1 Abstract .......................................................................................................................... 30 3.2 Introduction .................................................................................................................... 30 3.3 Experimental .................................................................................................................. 33 3.3.1 Materials and methods ............................................................................................ 33 3.3.2 Oxidation of pullulan with TEMPO and NaOCl/NaBr........................................... 35 3.3.3 Etherification of 6-carboxypullulan TBA salt ........................................................ 36 3.3.4 General procedure for the etherification of 6-carboxypullulan TBA salt ............... 37 3.3.5 Synthesis of 6-carboxypullulan ethers by reaction with iodomethane and iodoethane .............................................................................................................................. 37 3.4 Results and Discussion ................................................................................................... 38 3.4.1 Pullulan oxidation ................................................................................................... 38 3.4.2 Synthesis and characterization of 6-carboxypullulan ethers ................................... 39 3.4.3 Determination of critical micelle concentration of 6-carboxypullulan ethers ........ 48 3.5 Conclusions .................................................................................................................... 50