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Table Of Contents

Basic principles
1. The solid phase principle
2. Merrifield SPPS
3. Fmoc/tBu SPPS
3.3 Side-chain protecting groups
3.4 First residue attachment
3.5 Coupling step
3.6 N-Fmoc deprotection reaction
3.8 Enantiomerization
3.9 Side reactions
3.10 Cleavage reaction
References
Basic procedures
2. Manual synthesis
3. Resin handling
4. Resin functionalization
5. Attachment of the first residue
5.1 Hydroxymethyl-based resins
5.2 Trityl-based linkers
5.3 Aminomethyl-based linkers
6. Fmoc removal
7. Coupling methods
7.2 Active esters
7.3 Symmetrical anhydride
7.4 Aminium/phosphonium activation methods
7.5 Acid fluorides
8. Assembly of the peptide chain
9.2 Bromophenol blue monitoring
9.3 Fmoc determination
9.4 HPLC analysis
10.3 Peptide isolation
10.4 Monitoring the cleavage reaction
1. Introduction
2. Methionine
3. Cysteine
3.1 Cysteine protection
3.3 Formation of disulphides
Difficult peptides
2. Difficult peptides—an overview
2.1 Background
2.2 Identifying the effects of aggregation
2.3 Effect of resins, solvents, and additives on aggregation
3. Predicting difficult peptide sequences
4.1 Development and preparation of (Hmb)amino acid derivatives
4.3 Site selection for Hmb backbone protection
4.5 Use of Hmb protection to increase solution solubility
Synthesis of modified peptides
1. C-terminal modifications
1.1 Peptidyl N-alkyl amides
1.3 Peptide hydroxamic acids
1.4 Peptide aldehydes by solid phase synthesis
2. N-terminal modifications
2.1 Biotinylation
2.2 Reductive alkylation
3. Side-chain modifications
3.2 Strategy design in the synthesis of atypical peptides
Phosphopeptide synthesis
2. Building block approach
2.1 Introduction
2.2 Practical considerations
2.3 Illustrative examples
3. Global phosphorylation
3.2 General protocol for post-synthetic phosphorylation
3.3 Illustrative examples
3.4 Thiophosphorylated peptides
4. Analysis of phosphopeptides
4.1 HPLC analysis
4.2 Mass spectroscopy
Glycopeptide synthesis
2. Strategic considerations in glycopeptide synthesis
3. Formation of glycosidic linkages to amino acids
4. Choosing protective groups for glycosylated amino acids
4.1 Protection of the a-amino group
4.2 Protection of the a-carboxyl group
4.3 Protection of the carbohydrate hydroxyl groups
4.4 Suitable linkers and resins
5. Preparation of glycosylated amino acids
6. Synthesis of a glycopeptide from HIV gp120
Convergent peptide synthesis
1.1 Strategy in convergent synthesis
2. Solid phase synthesis of protected peptide fragments
2.1 Fragment selection
2.2 Synthesis of protected peptide fragments
3. Solid phase fragment condensation
3.2 Activation and condensation of protected peptide fragments
4. Phase and direction change
4.1 Fragment condensation in solution
2. Homobifunctional cross-linking
3. Heterobifunctional cross-linking
3.1 Conjugation of thiol-containing peptides to proteins
4.2 Synthesis of MAPs by fragment condensation
A. Chemoselective nonamide ligation
2. Chemoselective non-amide ligation
2.1 Thiol chemistry
2.2 Carbonyl chemistry
3. Orthogonal amide ligation
3.1 Carbonyl chemistry
3.2 Thiol chemistry
2.1 The concept of selective and reversible labelling
3. Capping of unreacted polypeptide chains in SPPS
4. RP-HPLC using lipophilic chromatographic
2. Batchwise peptide synthesis
2.1 PE Biosystems Model 433A peptide synthesis system
2.2 Protein Technologies, Inc., SONATA/Pilot™ peptide
2.3 Protein Technologies Inc., Model PS3™ peptide
2.4 Advanced ChemTech Model 90 peptide synthesizer
2,5 Advanced ChemTech Model 400 production-scale
2.6 ABIMED EPS 221 synthesizer
3. Continuous-flow peptide synthesis
3.1 PE Biosystems Pioneer™ peptide synthesis system
4. Multiple peptide synthesis systems
4.1 PE Biosystems Pioneer MPS option
4.4 ABIMED AMS 422 multiple peptide synthesizer
4.5 ABIMED ASP 222 Auto-Spot Robot
4.6 ZINSSER ANALYTIC SMPS 350 multiple peptide
4.7 ZINSSER ANALYTIC SOPHAS solid phase synthesizer
4.8 SHIMADZU PSSM-8 peptide synthesizer
5. Conclusions
Manual multiple synthesis methods
1. Simultaneous multiple peptide synthesis—the T-bag method
2.2 Synthesis of peptide SPOT-arrays
2.3 Applications of peptide SPOT-arrays
3.2 Chemistry
4.3 Peptide synthesis
List of suppliers
Index
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Fmoc Solid Phase Peptide Synthesis

Fmoc Solid Phase Peptide Synthesis

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Published by wvickery_1
Solid Phase Peptide Synthesis
Solid Phase Peptide Synthesis

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Published by: wvickery_1 on May 26, 2013
Copyright:Attribution Non-commercial

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08/27/2013

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