1. Introduction

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1. Introduction Introduction 1. INTRODUCTION........................................................................................ 4 1.1. A BRIEF HISTORY ..........................................................................................................................4 1.2. SOLID PHASE SYNTHESIS ..............................................................................................................6 1.3. SUPPORTS FOR SOLID PHASE SYNTHESIS ....................................................................................7 1.3.1. Styrene-divinylbenzene copolymers................................................................................................8 1.3.2. Polyacrylamides...............................................................................................................................9 1.3.3. Polyethylene glycol (PEG) ............................................................................................................ 10 1.3.4. Silica.............................................................................................................................................. 11 1.3.5. Other Supports............................................................................................................................... 12 1.4. ANALYTICAL METHODS ..............................................................................................................13 1.4.1. Combustion analysis...................................................................................................................... 13 1.4.2. Colorimetric assays........................................................................................................................ 13 1.4.3. Infrared and Raman spectroscopy.................................................................................................. 16 1.4.4. Mass spectrometry......................................................................................................................... 19 1.4.5. Nuclear Magnetic Resonance Spectroscopy.................................................................................. 19 1.5. SOLID PHASE ORGANIC SYNTHESIS ...........................................................................................20 1.6. SOLID PHASE PEPTIDE SYNTHESIS (SPPS)................................................................................21 1.6.1. Linkers........................................................................................................................................... 23 1.6.2. Protecting group strategy............................................................................................................... 29 1.6.3. Coupling reagents.......................................................................................................................... 33 1.6.4. Additives........................................................................................................................................ 40 1.7. MICROWAVE -ENHANCED SOLID PHASE SYNTHESIS ...................................................................41 1.7.1. Microwave application in solid-phase synthesis............................................................................ 41 1.7.2. General microwave physics........................................................................................................... 43 1.7.3. Microwave equipment ................................................................................................................... 46 1.7.4 CEM Liberty Automated Microwave Peptide Synthesizer............................................................ 48 1.8. FROM PRODUCTION OF PEPTIDES IN MILLIGRAM AMOUNTS FOR RESEARCH TO MULTI -TONS ® QUANTITIES FOR DRUGS : THE CASE OF FUZEON ......................................................................49 2. AIM OF THE THESIS .............................................................................. 53 3. RESULTS AND DISCUSSION ................................................................ 54 3.1. A BRIEF HISTORY : SYNBEADS OF FIRST GENERATION ...............................................................54 3.2. DEVELOPMENT OF AMINOMETHYL SYNBEADS ..........................................................................60 3.2.1. Influence of amino spacer.............................................................................................................. 60 3.2.2. Effect of density of functional groups ........................................................................................... 62 3.2.3. Preparation, characterisation, properties of aminomethyl Synbeads A310 ................................... 64 3.2.4. Chemical stability of aminomethyl Synbeads A310...................................................................... 68 Introduction 3.3. PREPARATION AND CHARACTERISATION OF SYNBEADS WITH OTHER FUNCTIONAL GROUPS .70 3.3.1. Preparation and characterisation of chloromethyl Synbeads C310................................................ 71 3.3.2. Preparation and characterisation of bromomethyl Synbeads B310 .............................................. 74 3.3.3. Effect of functional groups on the porosity of Synbeads............................................................... 75 3.3.4. Preparation and characterisation of carboxymethyl Synbeads X310............................................. 76 3.3.5. Preparation and characterisation of hydroxymethyl Synbeads H310 ............................................ 82 3.4. APPLICATION OF SYNBEADS IN SOLID PHASE PEPTIDE SYNTHESIS ...........................................85 3.4.1. Preparation of Wang-Synbeads ..................................................................................................... 85 3.4.2. Preparation of HMPB-Synbeads.................................................................................................... 87 3.4.3. Preparation of Rink Amide-Synbeads ........................................................................................... 88 3.4.4. Preparation of bromoacetal-Synbeads ........................................................................................... 89 3.4.5. Peptide synthesis on Synbeads A310............................................................................................. 91 3.4.6. Microwave assisted synthesis of peptides on Synbeads A310..................................................... 103 3.4.7. Set up of protocols for microwave assisted peptide synthesis on Synbeads................................ 105 3.5. FUNCTIONAL GROUPS DISTRIBUTION ANALYSIS ......................................................................109 3.5.1. Understanding diffusion phenomena in Synbeads....................................................................... 109 3.5.2. ATR analysis ............................................................................................................................... 109 3.5.3. Analysis on grinded Synbeads..................................................................................................... 114 3.5.4. Distribution analysis.................................................................................................................... 116 3.6. UNDERSTANDING FUNCTIONAL GROUPS DISTRIBUTION ON METHACRYLIC POLYMERS ........127 3.6.1. Characteristics of the polymers ................................................................................................... 127 4. METHODS AND MATERIALS ............................................................ 137 4.1. MATERIALS ...............................................................................................................................137 4.2. INSTRUMENTS ...........................................................................................................................137 4.2.1. Particle size distribution .............................................................................................................. 137 4.2.2. B.E.T. analysis and mercury porosimeter.................................................................................... 138 4.2.3. HPLC analysis ............................................................................................................................. 138 4.2.4. Flitration ...................................................................................................................................... 138 4.2.5. UV analysis ................................................................................................................................. 138 4.2.6. IR analysis ................................................................................................................................... 138 4.2.7. Electron microscopy analysis ...................................................................................................... 139 4.2.8. MW assisted peptide synthesis .................................................................................................... 139 4.2.9. MASS spectrometry .................................................................................................................... 139 4.3. ANALYTICAL METHODS ............................................................................................................139 4.3.1. Ninhydrin test .............................................................................................................................. 139 4.3.2. Malachite Green test...................................................................................................................
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