Origins and synthesis of amino acids

Author(s)

• Hughes, Andrew B.

Bibliographic Information

Origins and synthesis of amino acids

edited by Andrew B. Hughes

（Amino acids, peptides and proteins in organic chemistry / edited by Andrew B. Hughes, v. 1）

Wiley-VCH, c2009

Note

Includes bibliographical references and index

Description and Table of Contents

Description

This is the first 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 first volume is clearly divided into two parts. The first section deals with the origins of extraterrestrial and "terrestrial" amino acids and their evolution. The second part looks at their production and synthesis, including recent developments in the synthesis of ss-Amino acids. 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, eu.wiley.com/WileyCDA/WileyTitle/productCd-3527335463

Table of Contents

List of Contributors XVII Part One Origins of Amino Acids 1 1 Extraterrestrial Amino Acids 3 Z. Martins and M.A. Sephton 1.1 Introduction 3 1.2 ISM 6 1.3 Comets 9 1.4 Meteorites 11 1.5 Micrometeorites and IDPs 23 1.6 Mars 23 1.7 Delivery of Extraterrestrial Amino Acid to the Earth and its Importance to the Origin of Life 24 1.8 Conclusions 26 References 27 2 ''Terrestrial'' Amino Acids and their Evolution 43 Stephen Freeland 2.1 Introduction 43 2.2 What are the 20 ''Terrestrial'' Amino Acids? 44 2.3 What do We Know about the Evolution of the Standard Amino Acid Alphabet? 49 2.4 Amino Acids that Life Passed Over: A Role for Natural Selection? 58 2.5 Why Does Life Genetically Encode L-Amino Acids? 64 2.6 Summary, Synthesis, and Conclusions 64 References 66 Part Two Production/Synthesis of Amino Acids 77 3 Use of Enzymes in the Synthesis of Amino Acids 79 Theo Sonke, Bernard Kaptein, and Hans E. Schoemaker 3.1 Introduction 79 3.2 Chemo-Enzymatic Processes to Enantiomerically Pure Amino Acids 80 3.3 Acylase Process 81 3.4 Amidase Process 83 3.5 Hydantoinase Process 88 3.6 Ammonia Lyase Processes 90 3.7 Aminotransferase Process 94 3.8 AADH Process 99 3.9 Conclusions 102 References 103 4 b-Amino Acid Biosynthesis 119 Peter Spiteller 4.1 Introduction 119 4.2 Biosynthesis of b-Amino Acids 120 4.3 Conclusions and Future Prospects 154 References 155 5 Methods for the Chemical Synthesis of Noncoded a-Amino Acids found in Natural Product Peptides 163 Stephen A. Habay, Steve S. Park, Steven M. Kennedy, and A. Richard Chamberlin 5.1 Introduction 163 5.2 Noncoded CAAs 164 5.3 Noncoded Amino Acids by Chemical Modification of Coded Amino Acids 185 5.4 Noncoded Amino Acids with Elaborate Side-Chains 205 5.5 Conclusions 226 References 226 6 Synthesis of N-Alkyl Amino Acids 245 Luigi Aurelio and Andrew B. Hughes 6.1 Introduction 245 6.2 N-Methylation via Alkylation 246 6.3 N-Methylation via Schiff .s Base Reduction 259 6.4 N-Methylation by Novel Methods 265 6.5 N-Alkylation of Amino Acids 280 References 286 7 Recent Developments in the Synthesis of b-Amino Acids 291 Yamir Bandala and Eusebio Juaristi 7.1 Introduction 291 7.2 Synthesis of b-Amino Acids by Homologation of a-Amino Acids 291 7.3 Chiral Pool: Enantioselective Synthesis of b-Amino Acids from Aspartic Acid, Asparagine, and Derivatives 298 7.4 Synthesis of b-Amino Acids by Conjugate Addition of Nitrogen Nucleophiles to Enones 300 7.5 Synthesis of b-Amino Acids via 1,3-Dipolar Cycloaddition 312 7.6 Synthesis of b-Amino Acids by Nucleophilic Additions 316 7.7 Synthesis of b-Amino Acids by Diverse Addition or Substitution Reactions 328 7.8 Synthesis of b-Amino Acids by Stereoselective Hydrogenation of Prochiral 3-Aminoacrylates and Derivatives 330 7.9 Synthesis of b-Amino Acids by use of Chiral Auxiliaries: Stereoselective Alkylation 334 7.10 Synthesis of b-Amino Acids via Radical Reactions 338 7.11 Miscellaneous Methods for the Synthesis of b-Amino Acids 340 7.12 Conclusions 347 7.13 Experimental Procedures 348 8 Synthesis of Carbocyclic b-Amino Acids 367 Lorand Kiss, Enik}o Forro, and Ferenc Fuloep 8.1 Introduction 367 8.2 Synthesis of Carbocyclic b-Amino Acids 368 8.3 Synthesis of Functionalized Carbocyclic b-Amino Acid Derivatives 385 8.4 Enzymatic Routes to Carbocyclic b-Amino Acids 393 8.5 Conclusions and Outlook 398 8.6 Experimental Procedures 399 References 405 9 Synthetic Approaches to a,b-Diamino Acids 411 Alma Viso and Roberto Fernandez de la Pradilla 9.1 Introduction 411 9.2 Construction of the Carbon Backbone 411 9.3 Introduction of the Nitrogen Atoms in the Carbon Backbone 425 9.4 Conclusions 433 9.5 Experimental Procedures 434 References 435 10 Synthesis of Halogenated a-Amino Acids 441 Madeleine Strickland and Christine L. Willis 10.1 Introduction 441 10.2 Halogenated Amino Acids with a Hydrocarbon Side-Chain 442 10.3 Halogenated Amino Acids with an Aromatic Side-Chain 457 10.4 Halogenated Amino Acids with Heteroatoms in the Aliphatic Side-Chain 463 References 466 11 Synthesis of Isotopically Labeled a-Amino Acids 473 Caroline M. Reid and Andrew Sutherland 11.1 Introduction 473 11.2 Enzyme-Catalyzed Methods 473 11.3 Chiral Pool Approach 477 11.4 Chemical Asymmetric Methods 483 11.5 Conclusions 488 11.6 Experimental Procedures 489 References 491 12 Synthesis of Unnatural/Nonproteinogenic a-Amino Acids 495 David J. Ager 12.1 Introduction 495 12.2 Chemical Methods 497 12.3 Enzymatic Methods 508 12.4 Conclusions 516 12.5 Experimental Procedures 516 References 520 13 Synthesis of g- and d-Amino Acids 527 Andrea Trabocchi, Gloria Menchi, and Antonio Guarna 13.1 Introduction 527 13.2 g-Amino Acids 528 13.3 d-Amino Acids 547 13.4 Conclusions 566 References 567 14 Synthesis of g-Aminobutyric Acid Analogs 573 Jane R. Hanrahan and Graham A.R. Johnston 14.1 Introduction 573 14.2 a-Substituted g-Amino Acids 575 14.3 b-Substituted g-Amino Acids 579 14.4 g-Substituted g-Amino Acids 592 14.5 Halogenated g-Amino Acids 599 14.6 Disubstituted g-Amino Acids 600 14.7 Trisubstituted g-Amino Acids 604 14.8 Hydroxy-g-Amino Acids 605 14.9 Unsaturated g-Amino Acids 640 14.10 Cyclic g-Amino Acids 644 14.11 Conclusions 666 14.12 Experimental Procedures 666 References 677 Index 691

by "Nielsen BookData"

• NCID: BA91629254
• ISBN:
  • 9783527320967
• Country Code: gw
• Title Language Code: eng
• Text Language Code: eng
• Place of Publication: Weinheim
• Pages/Volumes: xix, 701 p.
• Size: 25 cm
• Classification:
  • DC22 : 547.7
• Subject Headings:
  • LCSH : Amino acids
  • LCSH : Peptides
  • LCSH : Proteins
  • LCSH : Amino acids -- Synthesis
• Parent Bibliography ID:
  • BA91629221