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TITLE
DEDICATION
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
LIST OF NOTATIONS AND ABBREVIATIONS
CONTENTS
1. INTRODUCTION AND OBJECTIVES
1.1 Introduction
1.2 Objectives of the present work
1.3 Organisation of the thesis
References
2. CHEMICAL SYNTHESIS OF PEPTIDES
2.1 Introduction
2.2 Methods of peptide synthesis-an overview
2.3 Strategy and tactics in SPPS
2.4. Boc versus Fmoc-chemistry
2.5 Peptide bond formation
2.6 Purification and characterisation
2.7 Solid-phases in SPPS
2.8 Problems in SPPS
2.8.1 Polymer matrix effect
2.8.2 Difficult sequences
2.9 Side reactions in SPPS
References
3. EXPERIMENTAL
3.1. Materials and methods
3.2. Purification of solvents
3.3. Preparation of crosslinked polymers
3.3.1 BDDMA-crosslinked polystyrene
3.3.2 DVB-crosslinked polystyrene
3.4. Swelling studies
3.5. Preparation of variously functionalised BDDMA-PS
3.5.1 Reagents for functionalisation
3.5.2 Functionalisation of BDDMA-PS
3.6. Preparation of amino acid derivatives and reagents for SPPS
3.7. General methods adopted for SPPS
3.7.1 Attachment of carboxy terminal amino acid to the support
3.7.2 Estimation of degree of amino acid incorporation
3.7.3 N
3.7.4 Coupling procedures
3.7.5 Cleavage of peptide from the support
3.7.6 Purification of the crude peptides
3.7.7 Characterisation of the peptides
3.7.8 Monitoring the coupling reactions
3.8. Synthesis of model tripeptides
3.8.1 Synthesis of Val-Ala-Gly
3.8.2 Synthesis of Ala-Ala-Ala
3.8.3 Synthesis of Gly-Ala-Val
3.8.4 Synthesis of Ala-Val-lle
3.8.5 Synthesis of Gly-Phe-Leu
3.8.6 Synthesis of Gly-Ala-Pro
3.8.7 Cleavage of peptides from BDDMA-PS
3.8.8 Characterisation
3.9. Synthesis of p-structured model difficult sequence peptides on2 mol% BDDMA-PS and DVB-PS supports
3.9.1 C-terminal amino acid anchoring to the support
3.9.2 Peptide chain assembly
3.9.3 Cleavage of peptides (i) to (vii) from BDDMA-PS support
3.9.4 Purification of the peptide
3.9.5 Characterisation of peptides
3.9.6 Synthesis of peptides (i) to (vii) on DVB-PS support
3.10. Synthesis of model hydrophobic peptides
3.10.1 Synthesis of decapeptide corresponding to the chemotacticdomain of elastin
3.10.2 Synthesis of bombyx-A fragments
3.10.3 Synthesis of CKS- 17 fragment (6- 17)
3.10.4 Synthesis of pamyloid plaque protein fragment (33-42)
3.11. Synthesis of difficult sequence peptides
3.11.1 Synthesis of ACP (65-74) fragment on BDDMA-PS and Merrifield support, DVB-PS
3.11.2 Synthesis of D-AIa17 analogue of human gonudofropin releasinghormone precursor protein fragment (14-36)
3.11.3 Synthesis of HIV- 1 asaprtyl protease (80-99) fragment
3.12. Synthesis of biologically active peptides
3.12.1 Synthesis of Leu[51]-enkephalin
3.12.2 Synthesis of delta sleep inducing peptide
3.12.3 Synthesis of C3-pepfide in volved in cell-proliferation regulation
3.12.4 Synthesis of CKS- 17
3.12.5 Synthesis of [Thr]3 [Thr]17 [Ser]11-galanine (1-19) analogue
3.12.6 Synthesis of chromostatin
References
4. RESULTS AND DISCUSSION
4.1. Preparation and characterisation of 1.4-butanediol dimethacrylate crosslinked polystyrene (BDDMA-PS)
4.2. Swelllng studias of BDDMA-PS
4.3. Functionalisation of BDDMA-PS
4.4. Stability of the polymer (BDDMA-PS)
4.5. Polymer morphology
4.6. Synthesis of model tripeptides
4.7. Synthesis of model difficult sequence peptides on BDDMA-PS and DVB-PS: A conelation between coupling difficulty and nature of the support
4.8. Synthesis of hydrophobic peptides
4.8.1 A decapeptide corresponding to the chemotactic domain of elastin
4.8.2 Synthesis of a decapeptide corresponding to the Bombyx-A fragment (1 9-28)
4.8.3 Synthesis of [Val24] [Pro28] Bombyx-A fragment (19-28)
4.8.4 Synthesis of CKS- 17 fragment (6- 17)
4.8.5 Synthesis of β-amyloid protein (33-42) fragment on PEG400 grafted copoly (styrene-2% BDDMA) support
4.9. Synthesis of difficult sequence peptides
4.10. Synthesis of biologically active peptides
4.10.1 Synthesis of Leu[5]-enkephalin
4.10.2 Synthesis of delta sleep inducing peptide (DSIP)
4.10.3 Synthesis of C3-peptide involved in the cell proliferation regulation
4.10.4 Synthesis of CKS- 17
4.10.5 Synthesis of [Thr14] [Thr191 galanine fragment (1 - 19)
4.10.6 Synthesis of chromostatin
4.11. Conclusion
References
5. CONFORMATIONAL ANALYSIS OF RESIN BOUND PEPTIDES
References
6. SUMMARY AND OUTLOOK