Amino Acids, Peptides and Proteins in Organic Chemistry, Modified Amino Acids, Organocatalysis and Enzymes

This is the second 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   Clearly structured in three main sections, this second volume in the series begins with the synthesis and chemistry of modified amino acids. The second part deals with the catalysis of reactions by amino acids, while the final section is devoted to enzymes, including proteases as catalysts, semisynthetic enzymes, catalysis by peptide-based enzyme models, substrate and protein recognition, as well as mammalian and insect peptide hormones.   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.

Table of Contents:
List of Contributors XIX Part One Synthesis and Chemistry of Modified Amino Acids 1 1 Synthesis and Chemistry of a,b-Didehydroamino Acids 3 Uli Kazmaier 1.1 Introduction 3 1.2 Synthesis of DDAAs 3 1.3 Reactions of DDAAs 14 1.4 Conclusions 21 1.5 Experimental Procedures 22 2 Synthesis and Chemistry of a-Hydrazino Acids 35 Joëlle Vidal 2.1 Introduction 35 2.2 Synthesis 41 2.3 Chemistry 63 2.4 Conclusions 78 2.5 Experimental Procedures 79 3 Hydroxamic Acids: Chemistry, Bioactivity, and Solution and Solid-Phase Synthesis 93 Darren Griffith, Marc Devocelle, and Celine J. Marmion 3.1 Introduction 93 3.2 Chemistry, Bioactivity, and Clinical Utility 93 3.3 Solution-Phase Synthesis of Hydroxamic Acids 106 3.4 Solid-Phase Synthesis of Hydroxamic Acids 121 3.5 Conclusions 130 3.6 Experimental Procedures 130 References 137 4 Chemistry of a-Aminoboronic Acids and their Derivatives 145 Valery M. Dembitsky and Morris Srebnik 4.1 Introduction 145 4.2 Synthesis of a-Aminoboronic Acids 146 4.3 Synthesis of a-Amidoboronic Acid Derivatives 146 4.4 Asymmetric Synthesis via a-Haloalkylboronic Esters 151 4.5 Synthesis of Glycine a-Aminoboronic Acids 154 4.6 Synthesis of Proline a-Aminoboronic Acids 155 4.7 Synthesis of Alanine a-Aminoboronic Acids 162 4.8 Synthesis of Ornithine a-Aminoboronic Acids 164 4.9 Synthesis of Arginine a-Aminoboronic Acids 167 4.10 Synthesis of Phenethyl Peptide Boronic Acids 170 4.11 Synthesis via Zirconocene Species 172 4.12 Synthesis and Activity of Amine-Carboxyboranes and their Derivatives 174 4.13 Synthesis of Boron Analogs of Phosphonoacetates 179 4.14 Conclusions 183 References 183 5 Chemistry of Aminophosphonic Acids and Phosphonopeptides 189 Valery P. Kukhar and Vadim D. Romanenko 5.1 Introduction 189 5.2 Physical/Chemical Properties and Analysis 191 5.3 Synthesis of a-Aminophosphonic Acids 193 5.4 Synthesis of b-Aminophosphonates 212 5.5 Synthesis of g-Aminophosphonates and Higher Homologs 219 5.6 Phosphono- and Phosphinopeptides 227 5.7 Remarks on the Practical Utility of Aminophosphonates 240 5.8 Conclusions 245 5.9 Experimental Procedures 246 References 249 6 Chemistry of Silicon-Containing Amino Acids 261 Yingmei Qi and Scott McN. Sieburth 6.1 Introduction 261 6.2 Synthesis of Silicon-Containing Amino Acids 263 6.3 Reactions of Silicon-Containing Amino Acids 271 6.4 Bioactive Peptides Incorporating Silicon-Substituted Amino Acids 272 6.5 Conclusions 275 6.6 Experimental Procedures 276 References 278 Part Two Amino Acid Organocatalysis 281 7 Catalysis of Reactions by Amino Acids 283 Haibo Xie, Thomas Hayes, and Nicholas Gathergood 7.1 Introduction 283 7.2 Aldol Reaction 285 7.3 Mannich Reaction 298 7.4 a-Amination Reaction 306 7.5 Michael Reaction 308 7.6 Morita–Baylis–Hillman Reaction and Its Aza-Counterpart 319 7.7 Miscellaneous Amino Acid-Catalyzed Reactions 321 7.8 Sustainability of Amino Acid Catalysis 328 7.9 Conclusions and Expectations 330 7.10 Typical Procedures for Preferred Catalysis of Reactions by Amino Acids 330 References 333 Part Three Enzymes 339 8 Proteases as Powerful Catalysts for Organic Synthesis 341 Andrés Illanes, Fanny Guzmán, and Sonia Barberis 8.1 Enzyme Biocatalysis 341 8.2 Proteolytic Enzymes: Mechanisms and Characteristics 345 8.3 Proteases as Process Catalysts 348 8.4 Proteases in Organic Synthesis 350 8.5 Peptide Synthesis 350 8.6 Conclusions 360 References 361 9 Semisynthetic Enzymes 379 Usama M. Hegazy and Bengt Mannervik 9.1 Usefulness of Semisynthetic Enzymes 379 9.2 Natural Protein Biosynthesis 380 9.3 Sense Codon Reassignment 381 9.4 Missense Suppression 385 9.5 Evolving the Orthogonal aaRS/tRNA Pair 387 9.6 Nonsense Suppression 390 9.7 Mischarging of tRNA by Ribozyme 395 9.8 Evolving the Orthogonal Ribosome/mRNA Pair 396 9.9 Frame-Shift Suppression 397 9.10 Noncanonical Base Pairs 399 9.11 Chemical Ligation 401 9.12 Inteins 404 9.13 EPL 410 9.14 Post-Translational Chemical Modification 411 9.15 Examples of Semisynthetic Enzymes 415 9.16 Conclusions 419 References 419 10 Catalysis by Peptide-Based Enzyme Models 433 Giovanna Ghirlanda, Leonard J. Prins, and Paolo Scrimin 10.1 Introduction 433 10.2 Peptide Models of Hydrolytic Enzymes 434 10.3 Peptide Models of Heme Proteins 456 10.4 Conclusions 467 References 467 11 Substrate Recognition 473 Keith Brocklehurst, Sheraz Gul, and Richard W. Pickersgill 11.1 Recognition, Specificity, Catalysis, Inhibition, and Linguistics 473 11.2 Serine Proteinases 476 11.3 Cysteine Proteinases 480 11.4 Glycoside Hydrolases 485 11.5 Protein Kinases 488 11.6 aaRSs 490 11.7 Lipases 492 11.8 Conclusions 493 References 494 12 Protein Recognition 505 Robyn E. Mansfield, Arwen J. Cross, Jacqueline M. Matthews, and Joel P. Mackay 12.1 General Introduction 505 12.2 Nature of Protein Interfaces 506 12.3 Affinity of Protein Interactions 509 12.4 Measuring Protein Interactions 512 12.5 Coupled Folding and Binding 515 12.6 Regulation of Interactions by PTMs 519 12.7 Engineering and Inhibiting Protein–Protein Interactions 521 12.8 Conclusions 527 References 527 13 Mammalian Peptide Hormones: Biosynthesis and Inhibition 533 Karen Brand and Annette G. Beck-Sickinger 13.1 Introduction 533 13.2 Mammalian Peptide Hormones 534 13.3 Biosynthesis of Peptide Hormones 535 13.4 Inhibition of Biosynthesis 555 13.5 Conclusions 565 References 565 14 Insect Peptide Hormones 575 R. Elwyn Isaac and Neil Audsley 14.1 Introduction 575 14.2 Structure and Biosynthesis of Insect Peptide Hormones 576 14.3 Proctolin 578 14.4 Sex Peptide 580 14.5 A-Type Allatostatins 582 14.6 CRF-Related Diuretic Hormones (DH) 584 14.7 Insect Peptide Hormones and Insect Control 586 14.8 Conclusions 589 References 590 15 Plant Peptide Signals 597 Javier Narváez-Vásquez, Martha L. Orozco-Cárdenas, and Gregory Pearce 15.1 Introduction 597 15.2 Defense-Related Peptides 599 15.3 Peptides Involved in Growth and Development 605 15.4 Peptides Involved in Self-Recognition 615 15.5 Methods in Plant Regulatory Peptide Research 616 15.6 Conclusions 623 References 624 16 Nonribosomal Peptide Synthesis 631 Sean Doyle 16.1 Introduction 631 16.2 NRPs 632 16.3 NRP Synthetase Domains 635 16.4 PPTases 639 16.5 Experimental Strategies for NRPS Investigations 642 16.6 Non-NRPS 649 16.7 Conclusions 650 References 650 Index 657