Amino Acids, Peptides and Proteins in Organic Chemistry, Building Blocks, Catalysis and Coupling Chemistry E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Serie: Amino Acids, Peptides and Proteins in Organic Chemistry
• Sprache: Englisch

Seitenzahl: 998

Veröffentlichungsjahr: 2011

Beschreibung

This is the third of five books in the Amino Acids, Peptides and Proteins in Organic Synthesis series.

Closing a gap in the literature, this is the only series to cover this important topic in organic and biochemistry. Drawing upon the combined expertise of the international "who's who" in amino acid research, these volumes represent a real benchmark for amino acid chemistry, providing a comprehensive discussion of the occurrence, uses and applications of amino acids and, by extension, their polymeric forms, peptides and proteins.

The practical value of each volume is heightened by the inclusion of experimental procedures.

The 5 volumes cover the following topics:

Volume 1: Origins and Synthesis of Amino Acids

Volume 2: Modified Amino Acids, Organocatalysis and Enzymes

Volume 3: Building Blocks, Catalysis and Coupling Chemistry

Volume 4: Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis

Volume 5: Analysis and Function of Amino Acids and Peptides

This third volume in the series presents an in depth account of recent developments in the (bio-)synthesis of amino acids and peptides. Divided into two parts, the first section deals with amino acids as building blocks, including the generation of alpha-amino acids, beta-lactams, and heterocycles. The second section is devoted to the synthesis of peptides, with the focus on solid phase synthesis. However, solution phase peptide synthesis is covered as well, as are topics such as coupling reagents, chemical ligation, peptide purification and automation.

Originally planned as a six volume series, Amino Acids, Peptides and Proteins in Organic Chemistry now completes with five volumes but remains comprehensive in both scope and coverage.

Further information about the 5 Volume Set and purchasing details can be viewed here.

Leseprobe

Contents

Cover

Half Title page

Further Reading

Title page

Copyright page

List of Contributors

Part One: Amino Acids as Building Blocks

Chapter 1: Amino Acid Biosynthesis

1.1 Introduction

1.2 Glutamate and Glutamine: Gateways to Amino Acid Biosynthesis

1.3 Other Amino Acids from Ubiquitous Metabolites: Pyridoxal Phosphate-Dependent Routes to Aspartate, Alanine, and Glycine

1.4 Routes to Functionalized Three-Carbon Amino Acids: Serine, Cysteine, and Selenocysteine

1.5 Other Amino Acids from Aspartate and Glutamate: Asparagine and Side Chain Functional Group Manipulation

1.6 Aspartate and Glutamate Families of Amino Acids

1.7 Biosynthesis of Aliphatic Amino Acids with Modified Carbon Skeletons: Branched-Chain Amino Acids, Lysine, and Pyrrolysine

1.8 Biosynthesis of the Aromatic Amino Acids

1.9 Conclusions

References

Chapter 2: Heterocycles from Amino Acids

2.1 Introduction

2.2 Heterocycles Generated by Intramolecular Cyclizations

2.3 Heterocycles Generated by Intermolecular Cyclizations

2.4 Heterocycles Generated by Cycloadditions

2.5 Conclusions

2.6 Experimental Procedures

Acknowledgments

References

Chapter 3: Radical-Mediated Synthesis of α-Amino Acids and Peptides

3.1 Introduction

3.2 Free Radical Reactions

3.3 Radical Addition to Imine Derivatives

3.4 Radical Conjugate Addition

3.5 Conclusions

3.6 Experimental Protocols

References

Chapter 4: Synthesis of β-Lactams (Cephalosporins) by Bioconversion

4.1 Introduction

4.2 Biosynthetic Pathways of Cephalosporins and Penicillins

4.3 Production of 7-ACA by A. chrysogenum

4.4 Production of 7-ADCA by A. chrysogenum

4.5 Production of Penicillin G by A. chrysogenum

4.6 Production of Cephalosporins by P. chrysogenum

4.7 Conversion of Penicillin G and other Penicillins to DAOG by Streptomyces clavuligerus

4.8 Conclusions

References

Chapter 5: Structure and Reactivity of β-Lactams

5.1 Introduction

5.2 Structure

5.3 Reactivity

5.4 Hydrolysis

5.5 Aminolysis

5.6 Epimerization

References

Part Two: Amino Acid Coupling Chemistry

Chapter 6: Solution-Phase Peptide Synthesis

6.1 Principle of Peptide Synthesis

6.2 Protection Procedures

6.3 Chain Elongation Procedures

6.4 Final Deprotection Methods

References

Chapter 7: Solid-Phase Peptide Synthesis: Historical Aspects

7.1 Introduction

7.2 Selection of Compatible Synthetic Components

7.3 Racemization and Stepwise Peptide Assembly

7.4 Optimization of Synthetic Components

7.5 Foreshadowing of the Nobel Prize

7.6 Automation of SPPS

7.7 Impact of New Protecting Groups and Resin Linkages

7.8 Solid-Phase Organic Chemistry

7.9 Early Applications of SPPS to Small Proteins

7.10 Side-Reactions and Sequence-Dependent Problems

7.11 Rapid Expansion of Usage Leading to the Nobel Prize

7.12 From the Nobel Prize Forward to Combinatorial Chemistry

7.13 Protein Synthesis and Peptide Ligation

7.14 Conclusions

Acknowledgments

References

Chapter 8: Linkers for Solid-Phase Peptide Synthesis

8.1 Introduction

8.2 Immobilization via Carboxyl Group

8.3 Immobilization via Amino Group

8.4 Backbone Immobilization

8.5 Immobilization via Amino Acid Side-Chain

8.6 Conclusions

References

Chapter 9: Orthogonal Protecting Groups and Side-Reactions in Fmoc/tBu Solid-Phase Peptide Synthesis

9.1 Orthogonal Protecting Groups in Fmoc/tBu Solid-Phase Peptide Synthesis

9.2 Side-Reactions in Fmoc/tBu Solid-Phase Peptide Synthesis

References

Chapter 10: Fmoc Methodology: Cleavage from the Resin and Final Deprotection

10.1 Introduction

10.2 “Low” TFA-Labile Resins

10.3 “High” TFA-Labile Resins

10.4 Final Remarks

Acknowledgments

References

Chapter 11: Strategy in Solid-Phase Peptide Synthesis

11.1 Synthetic Strategies Utilizing Solid-Phase Peptide Synthesis Methods

11.2 Solid Support: Resins and Linkers

11.3 Developing the Synthetic Strategy: Selection of the Protecting Group Scheme

11.4 Resin Loading

11.5 SBS Peptide Chain Elongation: Coupling and Activation

11.6 Piperazine Formation

11.7 Solid-Phase Synthesis of Protected Peptide Segments

11.8 Fragment Condensation Approach: Convergent and Hybrid Syntheses

11.9 Cleavage from the Resin and Global Peptide Deprotection

11.10 Disulfide Bond-Containing Peptides

11.11 Native Chemical Ligation (NCL)

11.12 SPPS of Peptides Modified at their C-Terminus

11.13 Side-Chain-Modified Peptides

11.14 Cyclic Peptides

11.15 Large-Scale Solid-Phase Synthesis

11.16 Conclusions

References

Chapter 12: Peptide-Coupling Reagents

12.1 Introduction

12.2 Carbodiimides

12.3 Phosphonium Salts

12.4 Aminium/Uronium Salts

12.5 Fluoroformamidinium Coupling Reagents

12.6 Organophosphorus Reagents

12.7 Triazine Coupling Reagents

12.8 Mukaiyama’s Reagent

12.9 Conclusions

Acknowledgments

References

Chapter 13: Chemoselective Peptide Ligation: A Privileged Tool for Protein Synthesis

13.1 Introduction

13.2 Chemoselective Peptide Ligations Following a Capture/Rearrangement Strategy

13.3 Chemical Transformations for Cys-Free Ligations in Peptides and Proteins

13.4 Other Chemoselective Capture Strategies

13.5 Peptide Ligations by Chemoselective Amide-Bond-Forming Reactions

13.6 Strategies for the Ligation of Multiple Fragments

References

Chapter 14: Automation of Peptide Synthesis

14.1 Introduction

14.2 SPPS: From Mechanization to Automation

14.3 Deprotection Step: Monitoring and Control

14.4 Coupling Step: Monitoring and Control

14.5 Integrated Deprotection and Coupling Control

References

Chapter 15: Peptide Purification by Reversed-Phase Chromatography

15.1 RP-HPLC of Peptides

15.2 Peptide Properties

15.3 Chromatographic Principles

15.4 Prediction of Peptide Retention Times

15.5 Advantages of Reduced Scale

15.6 Two-Dimensional Chromatographic Methods

15.7 Peptide Analysis in Complex Biological Matrices

15.8 Standard Methods for Peptide Separations for Analysis by Hyphenated Techniques

15.9 Emerging Methods for Peptide Separations for Analysis by Hyphenated Techniques

15.10 Practical use of RP-HPLC for Purifying Peptides (Analytical and Preparative Scale)

References

Chapter 16: Difficult Peptides

16.1 Importance of Peptide Synthesis

16.2 Methods for Peptide Synthesis

16.3 Chemical Peptide Synthesis

16.4 “Difficult Peptide Sequences”

16.5 Means to Overcome Peptide Aggregation in SPPS

16.6 Monitoring the Synthesis of a “Difficult Peptide”

16.7 Conclusions

References

Index

Amino Acids, Peptides and Proteins in Organic Chemistry

Further Reading

Drauz, K., Gröger, H., May, O. (eds.)

Enzyme Catalysis in Organic Synthesis

Third completely revised and enlarged edition

3 Volumes2011ISBN: 978-3-527-32547-4

Fessner, W.-D., Anthonsen, T.

Modern Biocatalysis

Stereoselective and Environmentally Friendly Reactions

2009ISBN: 978-3-527-32071-4

Pignataro, B. (ed.)

Ideas in Chemistry and Molecular Sciences

Advances in Synthetic Chemistry

2010ISBN: 978-3-527-32539-9

Reek, J. N. H., Otto, S.

Dynamic Combinatorial Chemistry

2010ISBN: 978-3-527-32122-3

Lutz, S., Bornscheuer, U. T. (eds.)

Protein Engineering Handbook

2 Volume Set

2009ISBN: 978-3-527-31850-6

Sewald, N., Jakubke, H.-D.

Peptides: Chemistry and Biology

2009ISBN: 978-3-527-31867-4

Jakubke, H.-D., Sewald, N.

Peptides from A to Z

A Concise Encyclopedia

2008ISBN: 978-3-527-31722-6

Royer, J. (ed.)

Asymmetric Synthesis of Nitrogen Heterocycles

2009ISBN: 978-3-527-32036-3

Hecht, S., Huc, I. (eds.)

Foldamers

Structure, Properties, and Applications

2007ISBN: 978-3-527-31563-5

The Editor

Andrew B. HughesLa Trobe UniversityDepartment of ChemistryVictoria 3086Australia

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

Library of Congress Card No.: applied for

British Library Cataloguing-in-Publication DataA catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche NationalbibliothekThe Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de.

© 2011 WILEY-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

Print ISBN: 978-3-527-32102-5 E-pdf ISBN: 978-3-527-63181-0 E-Pub ISBN: 978-3-527-63305-0 Mobi ISBN: 978-3-527-64081-2

List of Contributors

Knut AdermannPharis Biotec GmbHFeodor-Lynen-Strasse 3130625 HannoverGermany

José Luis AdrioNeuron BPhAvda. de la Innovación 1, Edificio BICParque Tecnológico de ciencias de la Salud18100 ArmillaGranadaSpain

Fernando AlbericioInstitute for Research in BiomedicineBarcelona Science ParkBaldiri Reixac 1008028 BarcelonaSpainandNetworking Centre on Bioengineering,Biomaterials and Nanomedicine(CIBER-BBN)Barcelona Science ParkBaldiri Reixac 1008028 BarcelonaSpain

University of BarcelonaDepartment of Organic ChemistryMartí i Franqués 1-1108028 BarcelonaSpain

Andrea BagnoUniversity of PadovaDepartment of Chemical Process EngineeringVia Marzolo 935131 PadovaItaly

Kleomenis BarlosUniversity of PatrasDepartment of ChemistryRion-PatrasGreece

José Luis BarredoI+D BiologiaAntibióticos S.A.Avda. Antibióticos, 59-6124009 LeónSpain

Julie BletzInstitute for Systems Biology1441 North 34th StreetSeattle, WA 98103-8904USA

Jeffrey W. BodeEidgenössische TechnischeHochschule ZürichLaboratorium für Organische ChemieWolfgang Pauli Strasse 108093 ZürichSwitzerland

M. Isabel CalazaUniversidad de Zaragoza – CSICInstituto de Ciencia de Materiales de AragónDepartamento de Química Orgánica50009 ZaragozaSpain

Stefano CarganicoUniversity of FirenzePolo Scientifico e TecnologicoLaboratory of Peptide and Protein Chemistry and BiologyVia della Lastruccia 1350019 Sesto FlorentinoItaly

PRES University of Cergy-PontoiseLaboratoire SOSCO-UMR 81235 mail Gay-Lussac, Neuville sur Oise95031 Cergy-PontoiseFrance

Carlos CativielaUniversidad de Zaragoza – CSICInstituto de Ciencia de Materiales de AragónDepartamento de Química Orgánica50009 ZaragozaSpain

Arnold L. DemainDrew UniversityRISEHS-330Madison, NJ 07940USA

Jan DeskaStockholm UniversityArrhenius LaboratoryDepartment of Organic Chemistry106 91 StockholmSweden

Monica DettinUniversity of PadovaDepartment of Chemical Process EngineeringVia Marzolo 935131 PadovaItaly

Carlo Di BelloUniversity of PadovaDepartment of Chemical Process EngineeringVia Marzolo 935131 PadovaItaly

Ayman El-FahamKing Saud UniversityCollege of ScienceDepartment of ChemistryPO Box 24551451 RiyadhKingdom of Saudi Arabia

Alexandria UniversityFaculty of ScienceDepartment of ChemistryHorria Street, PO Box 246, Ibrahimia21321 AlexandriaEgypt

Institute for Research in BiomedicineBarcelona Science ParkBaldiri Reixac 1008028 BarcelonaSpain

Christian P.R. HackenbergerFreie Universität BerlinInstitut für Chemie und BiochemieTakustrasse 314195 BerlinGermany

Jan HlaváPalacky UniversityDepartment of Organic ChemistryTrida 17, Listopadu 12771 46 OlomoucCzech Republic

Steven A. KatesIschemix63 Great RoadMaynard, MA 01754USA

Viktor KrchñákUniversity of Notre DameDepartment of Chemistry and Biochemistry251 Nieuwland Science CenterNotre Dame, IN 46556USA

Ulrike KusebauchInstitute for Systems Biology1441 North 34th StreetSeattle, WA 98103-8904USA

Cleber W. LiriaUniversity of São PauloInstitute of ChemistryDepartment of Biochemistry Peptide Chemistry LaboratoryAv. Prof. Lineu Prestes, 74805508-900 São PauloBrazil

Garland R. MarshallWashington UniversityCenter for Computational BiologyDepartments of Biochemistry andMolecular Biophysics and Biomedical Engineering700 S. Euclid AvenueSt. Louis, MO 63110USA

Joshua McBeeInstitute for Systems Biology1441 North 34th StreetSeattle, WA 98103-8904USA

Maria Terêsa Machini MirandaUniversity of São PauloInstitute of ChemistryDepartment of BiochemistryPeptide Chemistry LaboratoryAv. Prof. Lineu Prestes, 74805508-900 São PauloBrazil

Robert L. MoritzInstitute for Systems Biology1441 North 34th StreetSeattle, WA 98103-8904USA

Yoshio OkadaKobe Gakuin UniversityFaculty of Pharmaceutical SciencesArise 518, Ikawadani-cho, Nishi-ku651-2180 KobeJapan

Michael l. PageUniversity of HuddersfieldDepartment of Chemical and Biological SciencesQueensgateHuddersfield HD1 3DHUK

Anna Maria PapiniUniversity of FirenzePolo Scientifico e TecnologicoLaboratory of Peptide and Protein Chemistry and BiologyVia della Lastruccia 1350019 Sesto FlorentinoItaly

PRES University of Cergy-PontoiseLaboratoire SOSCO-UMR 81235 mail Gay-Lussac, Neuville sur Oise95031 Cergy-PontoiseFrance

Emily J. ParkerUniversity of CanterburyDepartment of ChemistryPO Box 4800ChristchurchNew Zealand

Andrew J. PrattUniversity of CanterburyDepartment of ChemistryPO Box 4800ChristchurchNew Zealand

Cesar RemuzgoUniversity of São PauloInstitute of ChemistryDepartment of Biochemistry Peptide Chemistry LaboratoryAv. Prof. Lineu Prestes, 74805508-900 São PauloBrazil

Marta Rodriguez-SáizAntibióticos S.A.Avda. Antibióticos, 59-6124009 LeónSpain

Dirk SchwarzerLeibniz-Institut für MolekularePharmakologie (FMP)Chemical Biology SectionRobert-Rössle-Strasse 1013125 BerlinGermany

Richard J. SimpsonLudwig Institute For Cancer ResearchJoint Proteomics LaboratoryRoyal Melbourne HospitalParkville, Victoria 3050Australia

Miroslav SouralPalacky UniversityDepartment of Organic ChemistryTrida 17, Listopadu 12771 46 OlomoucCzech Republic

Yuko TsudaKobe Gakuin UniversityFaculty of Pharmaceutical SciencesMinatojima 1-1-3, Chuo-ku650-8586 KobeJapan

Judit Tulla-PucheInstitute for Research in BiomedicineBarcelona Science ParkBaldiri Reixac 1008028 BarcelonaSpainandNetworking Centre on Bioengineering,Biomaterials and Nanomedicine(CIBER-BBN)Barcelona Science ParkBaldiri Reixac 1008028 BarcelonaSpain

Part One

Amino Acids as Building Blocks