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Fmoc Solid Phase Peptide Synthesis: A Practical Approach [Pehme köide]

Edited by (School of Pharmaceutical Sciences, University of Nottingham), Edited by (, Calbiochem/Novabiochem (UK), Nottingham)
  • Formaat: Paperback / softback, 370 pages, kõrgus x laius x paksus: 234x157x21 mm, kaal: 573 g, numerous illustrations
  • Sari: Practical Approach Series 222
  • Ilmumisaeg: 16-Dec-1999
  • Kirjastus: Oxford University Press
  • ISBN-10: 0199637245
  • ISBN-13: 9780199637249
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  • Formaat: Paperback / softback, 370 pages, kõrgus x laius x paksus: 234x157x21 mm, kaal: 573 g, numerous illustrations
  • Sari: Practical Approach Series 222
  • Ilmumisaeg: 16-Dec-1999
  • Kirjastus: Oxford University Press
  • ISBN-10: 0199637245
  • ISBN-13: 9780199637249
Teised raamatud teemal:
In the years since the publication of Atherton and Sheppard's volume, the technique of Fmoc solid-phase peptide synthesis has matured considerably and is now the standard approach for the routine production of peptides. The basic problems at the time of publication of this earlier work have now for the most part, been solved. As a result, innovators in the field have focussed their efforts to develop methodologies and chemistry for the synthesis of more complex structures. The focus of this new volume is much broader, and covers the essential procedures for the production of linear peptides and more advanced techniques for preparing cyclic, side-chain modified, phospho- and glycopeptides. Many other methods also deserving attention have been included: convergent peptide synthesis; peptide-protein conjugation; chemoselective ligation; and chemoselective purification. The difficult preparation of cysteine and methionine-containing peptides is also covered, as well as methods for overcoming aggregation during peptide chain assembly. Many of the techniques developed for the production of large arrays of peptides by parallel synthesis, such as t-bag, SPOT and PIN synthesis, have naturally been included. Finally, a survey of available automated instrumentation has also been provided.

Arvustused

'covers the essential procedures for the production of linear peptides, and the techniques for preparing cyclic, side-chain modified, phospho-and glycopeptides' Sciences de la vie '..a completly fresh book.....a goldmine...' European Petide Society

List of Contributors xvii Abbreviations xxi Introduction---a retrospective viewpoint 1(8) R. C. Sheppard Basic principles 9(32) Peter D. White Weng C. Chan The solid phase principle 9(2) Merrifield SPPS 11(1) Fmoc/tBu SPPS 11(30) Resins 13(2) Linkers 15(11) Side-chain protecting groups 26(1) First residue attachment 26(1) Coupling step 27(1) N-Fmoc deprotection reaction 27(3) Aggregation 30(1) Enantiomerization 31(1) Side reactions 32(4) Cleavage reaction 36(1) Limitations 36(1) References 37(4) Basic procedures 41(36) Weng C. Chan Peter D. White Introduction 41(1) Manual synthesis 41(1) Resin handling 41(3) Resin functionalization 44(1) Attachment of the first residue 44(7) Hydroxymethyl-based resins 44(6) Trityl-based linkers 50(1) Aminomethyl-based linkers 51(1) Fmoc removal 51(1) Coupling methods 52(8) DIC/HOBt 53(1) Active esters 54(1) Symmetrical anhydride 55(2) Aminium/phosphonium activation methods 57(2) Acid fluorides 59(1) Assembly of the peptide chain 60(1) Analytical procedures 61(3) Resin tests 61(1) Bromophenol blue monitoring 62(1) Fmoc determination 62(1) HPLC analysis 63(1) TFA-mediated cleavage 64(13) Preparing the resin for cleavage 64(1) Cleavage reactions releasing fully deprotected peptides 65(5) Peptide isolation 70(2) Monitoring the cleavage reaction 72(1) Release of fully protected peptides from hyper-acid labile supports with 1% TFA 73(1) References 74(3) Preparation and handling of peptides containing methionine and cysteine 77(38) Fernando Albericio Ioana Annis Mirian Royo George Barany Introduction 77(1) Methionine 78(3) Cysteine 81(34) Cysteine protection 81(6) Solid phase synthesis of cysteine-containing peptides 87(4) Formation of disulphides 91(18) References 109(6) Difficult peptides 115(22) Martin Quibell Tony Johnson Introduction 115(1) Difficult peptides--an overview 115(4) Background 115(2) Identifying the effects of aggregation 117(1) Effect of resins, solvents, and additives on aggregation 118(1) Predicting difficult peptide sequences 119(3) The N-(2-hydroxy-4-methoxybenzyl) (Hmb) backbone amide protecting group 122(15) Development and preparation of (Hmb) amino acid derivatives 122(3) Incorporation of N-(2-hydroxy-4-methoxybenzyl)amino acid residues 125(2) Site selection for Hmb back bone protection 127(1) Improved difficult peptide syntheses through Hmb backbone protection 128(3) Use of Hmb protection to increase solution solubility 131(1) References 132(5) Synthesis of modified peptides 137(46) Sarah L. Mellor Donald A. Wellings Jean-Alain Fehrentz Marielle Paris Jean Martinez Nicholas J. Ede Andrew M. Bray David J. Evans G. B. Bloomberg C-terminal modifications 137(29) Peptidyl N-alkyl amides 137(4) Use of the 4-hydroxymethylbenzoic acid linkage agent for the synthesis of C-terminal modified peptides 141(8) Peptide hydroxamic acids 149(4) Peptide aldehydes by solid phase synthesis 153(8) Synthesis of C-terminal peptide aldehydes on the Multipin™ system using the oxazolidine linker 161(5) N-terminal modifications 166(3) Biotinylation 167(1) Reductive alkylation 168(1) Side-chain modifications 169(14) Introduction 169(1) Strategy design in the synthesis of atypical peptides 169(9) References 178(5) Phosphopeptide synthesis 183(12) Peter D. White Introduction 183(1) Building block approach 183(4) Introduction 183(1) Practical considerations 184(1) Illustrative examples 185(2) Global phosphorylation 187(5) Introduction 187(2) General protocol for post-synthetic phosphorylation 189(1) Illustrative examples 190(1) Thiophosphorylated peptides 191(1) Analysis of phosphopetides 192(3) HPLC analysis 192(1) Mass spectroscopy 192(1) References 193(2) Glycopeptide synthesis 195(20) Jan Kihlberg Introduction 195(2) Strategic considerations in glycopeptide synthesis 197(1) Formation of glycosidic linkages to amino acids 198(2) Choosing protective groups for glycosylated amino acids 200(3) Protection of the α-amino group 200(1) Protection of the α-carboxyl group 201(1) Protection of the carbohydrate hydroxyl groups 201(1) Suitable linkers and resins 202(1) Preparation of glycosylated amino acids 203(6) Synthesis of a glycopetide from HIV gp120 209(6) References 211(4) Convergent peptide synthesis 215(14) Kleomenis Barlos Dimitrios Gatos Introduction 215(1) Strategy in convergent synthesis 215(1) Solid phase synthesis of protected peptide fragments 216(4) Fragment selection 216(1) Synthesis of protected peptide fragments 216(4) Solid phase fragment condensation 220(3) Esterification of the C-terminal fragment on 2-chlorotrityl chloride resin 220(1) Activation and condensation of protected peptide fragments 221(2) Phase and direction change 223(4) Fragment condensation in solution 223(2) Two-directional synthesis. Attachment of fragments on resins of the trityl-type through an amino acid side chain functional group 225(2) Deprotection, purification, and purity determination of the synthetic peptides 227(2) References 227(2) Methods of preparing peptide---carrier conjugates 229(14) Jan W. Drijfhout Peter Hoogerhout Introduction 229(1) Homobifunctional cross-linking 229(2) Heterobifunctional cross-linking 231(5) Conjugation of thiol-containing peptides to proteins 231(3) Conjugation of peptides to thiolated carriers 234(2) MAP-core constructs as peptide-carriers 236(7) Sequential synthesis of MAPs 237(1) Synthesis of MAPs by fragment condensation 237(2) References 239(4) Chemoselective and orthogonal ligation techniques 243(22) James P. Tam Y.-A. Lu Introduction 243(1) Chemoselective non-amide ligation 244(8) Thiol chemistry 245(2) Carbonyl chemistry 247(5) Orthogonal amide ligation 252(13) Carbonyl chemistry 252(6) Thiol chemistry 258(4) References 262(3) Purification of large peptides using chemoselective tags 265(12) Paolo Mascagni Introduction 265(1) Purification of large polypeptides using Fmoc-based chromatographic probes 266(2) The concept of selective and reversible labelling 266(2) Capping of unreacted polypeptide chains in SPPS 268(1) RP-HPLC using lipophilic chromatographic probes 269(5) Affinity chromatography using biotinylated chromatographic probes 274(3) References 276(1) Instrumentation for automated solid phase peptide synthesis 277(26) Linda E. Cammish Steven A. Kates Introduction 277(2) Batchwise peptide synthesis 279(8) PE Biosystems Model 433A peptide synthesis system 280(3) Protein Technologies, Inc., SONATA/Pilot™ peptide synthesizer 283(1) Protein Technologies Inc., Model PS3™ peptide synthesizer 283(1) Advanced ChemTech Model 90 peptide synthesizer 284(2) Advanced ChemTech Model 400 production-scale synthesizer 286(1) ABIMED EPS 221 synthesizer 287(1) Continuous-flow peptide synthesis 287(4) PE Biosystems Pioneer™ peptide synthesis system 289(2) Multiple peptide synthesis systems 291(8) PE Biosystems Pioneer MPS option 291(1) Protein Technologies, Inc., SYMPHONY/Multiplex™ peptide synthesizer 292(1) Advanced ChemTech Models 348, 396, and 357 bimolecular synthesizers 293(1) ABIMED AMS 422 multiple peptide synthesizer 294(2) ABIMED ASP 222 Auto-Spot Robot 296(1) ZINSSER ANALYTIC SMPS 350 multiple peptide synthesizer 297(1) ZINSSER ANALYTIC SOPHAS solid phase synthesizer 298(1) SHIMADZU PSSM-8 peptide synthesizer 298(1) Conclusions 299(4) References 300(3) Manual multiple synthesis methods 303(26) B. Dorner J. M. Ostresh R. A. Houghten Ronald Frank Andrea Tiepold John E. Fox Andrew M. Bray Nicholas J. Ede Ian W. James Geoffrey Wickham Simultaneous multiple peptide synthesis---the T-bag method 303(2) Introduction 303(1) The T-bag method 303(2) Multiple peptide synthesis with the SPOT-technique 305(9) Introduction 305(3) Synthesis of peptide SPOT-arrays 308(5) Applications of peptide SPOT-arrays 313(1) Manual multipeptide synthesis in block arrays 314(5) Hardware 314(1) Chemistry 315(2) Software 317(2) Synthesis of peptides by the Multipin™ method 319(10) Introduction 319(1) Linkers 320(1) Peptide synthesis 321(4) References 325(4) Appendices 329(12) A1 Equipment and reagents for peptide synthesis 329(2) A2 List of suppliers 331(6) A3 Useful tables 337(4) Index 341