Chemical Ligation: Tools for Biomolecule Synthesis and Modification

Presenting a wide array of information on chemical ligation one of the more powerful tools for protein and peptide synthesis this book helps readers understand key methodologies and applications that protein therapeutic synthesis, drug discovery, and molecular imaging.     Moves from fundamental to applied aspects, so that novice readers can follow the entire book and apply these reactions in the lab     Presents a wide array of information on chemical ligation reactions, otherwise scattered across the literature, into one source     Features comprehensive and multidisciplinary coverage that goes from basics to advanced topics     Helps researchers choose the right chemical ligation technique for their needs INDICE: List of Figures xiii .List of Plates xxiii .List of Contributors xxix .Preface xxxiii .1 Introduction to Chemical Ligation Reactions 1Lucia De Rosa, Alessandra Romanelli, and Luca Domenico D Andrea .1.1 Introduction 1 .1.2 Chemical Ligation Chemistries 6 .1.3 Imine Ligations 7 .1.4 Serine/Threonine Ligation (STL) 21 .1.5 Thioether Ligation 24 .1.6 Thioester Ligation 25 .1.7 Ketoacid Hydroxylamine (KAHA) Ligation 49 .1.8 Staudinger Ligation 52 .1.9 Azide Alkyne Cycloaddition 57 .1.10 Diels Alder Ligation 61 .References 64 .2 Protein Chemical Synthesis by SEA Ligation 89Oleg Melnyk, Claire Simonneau, and Jérôme Vicogne .2.1 Introduction 89 .2.2 Essential Chemical Properties of SEA Group 93 .2.3 Protein Total Synthesis Using SEA Chemistry SEAon/off Concept 97 .2.4 Chemical Synthesis of HGF/SF Subdomains for Deciphering the Functioning of HGF/SF–MET System 106 .2.5 Conclusion 114 .References 114 .3 Development of Serine/Threonine Ligation and Its Applications 125Tianlu Li and Xuechen Li .3.1 Introduction 125 .3.2 Serine/Threonine Ligation (STL) 130 .3.3 Application of STL in Protein Synthesis 140 .3.4 Conclusion and Outlook 154 .References 154 .4 Synthesis of Proteins by Native Chemical Ligation Desulfurization Strategies 161Bhavesh Premdjee and Richard J. Payne .4.1 Introduction 161 .4.2 Ligation Desulfurization and Early Applications 162 .4.3 Beyond Native Chemical Ligation at Cysteine The Development of Thiolated Amino Acids and Their Application in Protein Synthesis 174 .4.4 Ligation Deselenization in the Chemical Synthesis of Proteins 211 .4.5 Conclusions and Future Directions 216 .References 218 .5 Synthesis of Chemokines by Chemical Ligation 223Nydia Panitz and Annette G. Beck Sickinger .5.1 Introduction The Chemokine Chemokine Receptor Multifunctional System 223 .5.2 Synthesis of Chemokines by Native Chemical Ligation 224 .5.3 Synthesis of Chemokines by Alternative Chemical Ligation 231 .5.4 Semisynthesis of Chemokines by Expressed Protein Ligation 233 .5.5 Prospects 241 .References 243 .6 Chemical Synthesis of Glycoproteins by the Thioester Method 251Hironobu Hojo .6.1 Introduction 251 .6.2 Ligation Methods and Strategy of Glycoprotein Synthesis 252 .6.3 The Synthesis of the Extracellular Ig Domain of Emmprin 254 .6.4 Synthesis of Basal Structure of MUC2 256 .6.5 N Alkylcysteine Assisted Thioesterification Method and Dendrimer Synthesis 257 .6.6 Synthesis of TIM 3 260 .6.7 Resynthesis of Emmprin Ig Domain 262 .6.8 Conclusion 264 .References 264 .7 Membrane Proteins: Chemical Synthesis and Ligation 269Marc Dittman and Martin Engelhard .7.1 Introduction 269 .7.2 Methods for the Synthesis and Purification of Membrane Proteins 270 .7.3 Ligation and Refolding 273 .7.4 Illustrative Examples 276 .References 280 .8 Chemoselective Modification of Proteins 285Xi Chen, Stephanie Voss, and Yao–Wen Wu .8.1 Chemical Protein Synthesis 285 .8.2 Chemoselective and Bioorthogonal Reactions 287 .8.3 Site–Selective Protein Modification Approaches 307 .References 322 .9 Stable, Versatile Conjugation Chemistries for Modifying Aldehyde–Containing Biomolecules 339Aaron E. Albers, Penelope M. Drake and David Rabuka .9.1 Introduction 339 .9.2 Aldehyde as a Bioorthogonal Chemical Handle for Conjugation 339 .9.3 Aldehyde Conjugation Chemistries 340 .9.4 The Pictet Spengler Ligation 341 .9.5 The Hydrazinyl–Iso–Pictet Spengler (HIPS) Ligation 341 .9.6 The Trapped–Knoevenagel (thioPz) Ligation 343 .9.7 Applications Antibody Drug Conjugates 346 .9.8 Next–Generation HIPS Chemistry AzaHIPS 348 .9.9 Applications Protein Engineering 349 .9.10 Applications Protein Labeling 349 .9.11 Conclusions 351 .References 351 .10 Thioamide Labeling of Proteins through a Combination of Semisynthetic Methods 355Christopher R. Walters, John J. Ferrie, and E. James Petersson .10.1 Introduction 355 .10.2 Thioamide Synthesis 356 .10.3 Thioamide Incorporation into Peptides 357 .10.4 Synthesis of Full Sized Proteins Containing Thioamides 360 .10.5 Applications 368 .10.6 Conclusions 381 .Acknowledgments 381 .References 382 .11 Macrocyclic Organo–Peptide Hybrids by Intein–Mediated Ligation: Synthesis and Applications 391John R. Frost and Rudi Fasan .11.1 Introduction 391 .11.2 Macrocyclic Organo–Peptide Hybrids as Natural–Product–Inspired Macrocycles 396 .11.3 Application of MOrPHs for Targeting –Helix–Mediated Protein Protein Interactions 406 .11.4 Conclusions 410 .References 410 .12 Protein Ligation by HINT Domains 421Hideo Iwaï and A. Sesilja Aranko .12.1 Introduction 421 .12.2 Protein Ligation by Protein Splicing 423 .12.3 Naturally Occurring and Artificially Split Inteins for Protein Ligation 424 .12.4 Conditional Protein Splicing 427 .12.5 Inter– and Intramolecular Protein Splicing 429 .12.6 Protein Ligation by Other HINT Domains 430 .12.7 Bottleneck of Protein Ligation by PTS 432 .12.8 Comparison with Other Enzymatic Ligation Methods 432 .12.9 Perspective of Protein Ligation by HINT Domains 437 .12.10 Conclusions and Future Perspectives 438 .Acknowledgment 438 .References 438 .13 Chemical Ligation for Molecular Imaging 447Aurélien Godinat, Hacer Karatas, Ghyslain Budin, and Elena A. Dubikovskaya .13.1 Introduction 447 .13.2 Chemical Ligation 448 .13.3 Conclusion 470 .References 473 .14 Native Chemical Ligation in Structural Biology 485Lucia De Rosa, Alessandra Romanelli, and Luca Domenico D Andrea .14.1 Introduction 485 .14.2 Protein (Semi)synthesis for Molecular Structure Determination 486 .14.3 Protein (Semi)Synthesis for Understanding Protein Folding, Stability, and Interactions 494 .14.4 Protein (Semi)Synthesis in Enzyme Chemistry 501 References 506 .Index 517

• ISBN: 978-1-119-04410-9
• Editorial: Wiley–Blackwell
• Encuadernacion: Cartoné
• Páginas: 576
• Fecha Publicación: 02/05/2017
• Nº Volúmenes: 1
• Idioma: Inglés