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TITLE
DEDICATION
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
LIST OF ABBREVIATIONS
CONTENTS
1. INTRODUCTION
2. ACTIVATION OF CARBOXYL GROUPS IN PEPTIDE SYNTHESIS - A REVIEW
1. Introduction
2. Acid chlorides
3. Acid azides
4. Anhydrides
5. Esters
6. Coupling Reagents
7. Photochemical Activation
i) Nitroindolines
ii) 2-Thionothiazolidines
iii) 5-Azido-1.3.4-oxadiazoles
iv) Oxazole triamide rearrangement
3. ACTIVATION OF CARBOXYL GROUPS USING 2-MERCAPTOBENZOTHIAZQLE
1. Introduction
2. Results and Discussion
2.1 Synthesis of 3-benzoyl benzo thiazoline-2-thione
2.1 (i) Reaction of 3-benzoyl benzo thiazoline-2-thione with amines
2.1 (ii) Reaction of 3-benzoyl benzo thiazoline-2-thione with alcohols
2.1 (iii) Reaction of 3-benzoyl benzo thiazoline-2-thione with amino alcohols
2.2 Synthesis of 3- (phenylacetyl) benzothiazoline-2-thione
2.2 (i) Reaction of 3- (phenylacetyl) benzothiazoline-2-thione with amines
2.2 (ii) Reaction of 3-. (phenylacetyl) benzothiazoline-2-thione with alcohols
2.2 (iii) Reaction of 3- (phenylacetyl) benzothiazoline-2-thione with amino alcohols
2.3 Synthesis of 3-acetyl benzothiazoline-2-thione
2.3 (i) Reaction of 3-acetyl benzothiazoline-2-thione with amines
2.3 (ii) Reaction of 3-acetyl benzothiazoline-2-thione with alcohols
2.3 (iii) Reaction of 3-acetyl benzothiazoline-2-thione with amino alcohols
2.4 Synthesis of 3-propionyl benzothiazoline-2-thione
2.4 (i) Reaction of 3-propionyl benzothiazoline-2-thione with amines
2.4 (ii) Reaction of 3-propionyl benzothiazoline-2-thione with alcohols
2.4 (iii) Reaction of 3-propionyl benzothiazoline-2-thione with amino alcohols
3. Experimental
3.1 General
3.2 Synthesis of 3-benzoyl benzothiazoline-2-thione
3.2. (i) Reaction of 3-benzoyl benzothiazoline-2-thione (ha) with amines: Formation of amides
3.2 (ii) Reaction of 3-benzoyl benzothiazoline-2-thione (4a) with amino alcohols
3.3 Synthesis of 3- (phenylacetyl) benzothiazoline-2-thione
3.3. (i) Reaction of 3- (phenylacetyl) benzothiazoline-2-thione (4b) with amines: Formation of amides
3.3 (ii) Irradiation of 3- (phenylacetyl) benzothiazoline-2-thione (4b) with alcohols: Formation of esters
3.3 (iii) Reaction of 3- (phenylacetyl) benzothiazoline-2-thione (4b) with amino alcohols: Formation ofhydroxy amides
3.4 Synthesis of 3-acetyl benzothiazoline-2-thione
3.4 (i) Reaction of 3-acetyl benzothiazoline - 2 - thione (4c) with amines: Formation of amides
3.4 (ii) Irradiation of 3-acetyl benzothiazoline-2-thione (4c) in presence of alcohols: Formation of esters
3.4 (iii) Reactions of 3-acetyl benzothiazoline-2-thione (4c) with amino alcohols: Formation of hydroxyamides
3.5 Synthesis of 3-propionyl benzothiazoline-2-thione
3.5 (i) Reaction of 3-propionyl benzothiazoline-2-thione (4d) with amines: Formation of amides
3.5 (ii) Irradiation of 3-propionyl benzothiazoline-2-thione (4d) in presence of alcohols
3.5 (iii) Reaction of 3-propionyl benzothiazoline-2-thione (4d) with amino alcohols: Selective aminolysis
4. ACTIVATION OF CARBOXYL GROUPS USING 2-MERCAPTOBENZOXAZOLE
1. Introduction
2. Results and Discussion
2.1 Synthesis of 3-benzoyl benzoxazoline-2-thione
2.2 Reaction of 3-aryl benzoxazoline 2-thiones with amines
2.3 Reaction of 3-acyl benzoxazoline 2-thiones with alcohols under photochemical conditions
2.4 Reaction of 3-acyl benzoxazoline 2-thione with amino alcohols
3. Experimental
3.1 Synthesis of 3-acyl benzoxazoline-2-thiones (5a-e): General procedure
3.2. Reaction of 3-acyl benzoxazoline-2-thiones withamines: General procedure
3.3. Reaction of 3-acyl benzoxazoline-2-thione withalcohols: General procedure
3.4. Reaction of 3-acyl benzoxazoline-2-thione with aminoalcohols: General procedure
5. MONITORING OF AMINOLYSIS REACTIONS - A SPECTROPHOTOMETRIC INVESTIGATION
1. Introduction
2. Results and Discussion
2.1 UV-visible spectrum of 3-acyl benzothiazoline-2-thione
2.2 UV-visible spectrum of 3-acyl benzothiazoline-2-thione during aminolysis
2.3 UV-visible spectrum of 3-acyl benzoxazoline-2-thione
2.4 UV-visible spectrum of 3-acyl benzoxazoline-2-thione during aminolysis
3. Experimental
6. PEPTIDE SYNTHESIS
1. Introduction
2. Solid phase peptide synthesis - An overview
3. Synthesis of peptides
3.1 Synthesis of 3-[ (N-benzoyl) glycyl] benzothiazoline-2-thione
3.2 Synthesis of protected model peptides
3.3 Synthesis of 3-[ (Boc) glycyl] benzothiazoline-2-thione
3.4 Synthesis of dipeptide Boc-Gly-Phe-OMe (21e)
3.5 Synthesis of 3-[ (N-benzoyl!g1ycyl] benzoxazoline-2-thione
3.6 Synthesis of protected peptides
4. Peptide synthesis using solid phase strategy
4.1 Synthesis of dipeptide Ala-Gly
4.1 (i) Attachment of first amino acid - (Boc-Ala) on the resin
4.1 (ii) Preparation of activated Boc-Gly (4g)
4. (iii) Synthesis of dipeptide Ala-Gly (22a)
4.2 Synthesis of dipeptide Ala-Ala,
4.3 Synthesis of tripeptide Ala-Ala-Ala
4.4 Synthesis of tetrapeptide Ala-Gly-Gly-Gly
5. Materials and Methods
7. SUMMARY AND OUTLOOK
REFERENCES