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TITLE
CERTIFICATE
DECLARATION
ABBREVIATIONS
ACKNOWLEDGEMENT
CONTENTS
1. Introduction and Objectives
1.1 Objectives of the Present Work
1.2 Organization of the thesis
2. Solid Phase Peptide Synthesis: An Overview.
2.1 Principles of solid phase peptide synthesis
The Essential Advantages Associated with SPPS
The Limitations Associated with the Solid Phase Synthesis
2.2 Insoluble supports and anchoring linkages in SPPS
2.3 Use of Fmoc groups in peptide chemistry
2.4 Solvents in SPPS
2.5 New methods of protection and deprotection in SPPS
2.6 Coupling reagents in SPPS
2.7 Cleavage of the peptide-resin bond
2.8 Purification and characterization of cleaved peptides
2.9 S-S bridging in peptides
2.10 Synthesis of hydrophobic peptides
3. Results and Discussion
3. 1 Preparation of polymer supports and functionalization
3. 1. a Preparation of tetraethyleneglycol diacrylate crosslinked polystyrene support for solid phase peptide synthesis
3. 1. b Polymer synthesis
3. 1. c Functionalization of TTEGDA-cross linked polystyrene by chloromethylation
3. 1. d Functional group analysis
3. 2 Peptide synthesis using 2 mol% TTEGDA-crosslinked chloromethyl polystyrene
3. 2. a Details of the synthesized peptides
3. 2. b Solid phase synthesis of peptides using TTEGDA- crosslinked chloromethyl polystyrene
(i) Synthesis of model peptides
(a) Ala-Phe-Gly
(b) Gly-Gly-Gly
(c) Gly-Ala Ala
(d) Ac.Ala-Ala-Ala
(e) Asn-Ala-Gly-Ala
(f) Val-Gly-Val-Ala-Pro-Gly
(ii) Synthesis of hydrophobic peptides
(a) Ala-Cvs-Leu-Phe-Val-Dpro-Gly-Leu- Val- Val-Cys-Ala
(b) Val-Leu-Gly-Phe-Leu-Gly-Phe-Leu-Ala-Thr-A la-Gl- Ser-Ala-Met-Gly-Ala Ala-Ser-Leu
(c) Glu-Thr-Thr-Ala-Leu-Val-Ala Asp-Asn-Gly
(d) Tyr-Ala-GlyAla-Val-Val-Asn-Asp-Leu-Tyr-Gly-Ala-Val-Val-Asn-Asp-Leu
(iii) Synthesis of cystine peptides
(a) Cys-Pro-Leu-Cys-Gly-Ala
(b) Cys-Tvr-Ile-Gln-Asn-Cys-Pro-Leu-Gly
4. Experimental
4.1 Preparation of polymer supports and functionalization
4.1.a Materials and methods
4.1.b Source of chemicals
4.1.c Polymer synthesis
4.1.d Functionalization of PS- TTEGDA support with chloromethyl groups: General procedure
4.2 Peptide synthesis
4.2.a Source of chemicals
4.2.b Purification of reagents and solvents
4.2.c Physical measurements
4.2.d Detection
4.2.e Identification of plates on TLC
4.2.f Visualization
4.2.g Preparation of reagents and amino acid derivatives
4.2. h Preparation of 1-Hydroxybenzotriazole (HOBt)
4.2.i General procedure for solid phase peptide synthesis
4.2.j Attachment of first amino acid onto the resin
4.2.k Estimation of first amino acid substitution: Picric acid test
4.2.l Removal of t-butyloxycarbonyl group
4.2.m Methods of activation and coupling
4.2.n Cleavage of peptide from the resin: TFA / Thioanisole method
4.2.o Purification
4.2.p Synthesis of model peptides
4.2.q Synthesis of hydrophobic peptides
4.2.r Synthesis of cystine peptides
5. Summary and Outlook
References