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Methods of Non-I?-Amino Acid Synthesis, Second Edition

Overview

Although less common than α-amino acids, non-α-amino acids—where the amino group is not on the carbon immediately adjacent to the carboxyl group but is attached to another carbon in the chain (for example, the β, γ, δ carbon)—are components of biologically important molecules, are significant in the pharmaceutical industry, and are useful starting materials for many areas of organic chemistry. Since the publication of the first edition of this book nearly 20 years ago, synthetic work devoted to the preparation of...

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Overview

Although less common than α-amino acids, non-α-amino acids—where the amino group is not on the carbon immediately adjacent to the carboxyl group but is attached to another carbon in the chain (for example, the β, γ, δ carbon)—are components of biologically important molecules, are significant in the pharmaceutical industry, and are useful starting materials for many areas of organic chemistry. Since the publication of the first edition of this book nearly 20 years ago, synthetic work devoted to the preparation of non- α-amino acids has expanded greatly.

Methods of Non-α-Amino Acid Synthesis, Second Edition has been extensively rewritten and reorganized, providing an up-to-date review of strategies and methods for non-α-amino acid synthesis, particularly those amino acids that are key synthetic intermediates or important compounds in their own right. It focuses on acyclic amino acids of C3–C10, but also aminoalkanoic carboxylic acids, aminoalkenoic acids, and aminoalkynoic acids. The new edition contains many updated references and has a greater emphasis on the biological importance of non-α-amino acids. In addition to an array of synthetic methods, the book offers discussions on why non-α-amino acids are important.

The book covers synthetic methods that rely on substituent refunctionalization, the conversion of cyclic precursors to acyclic amino acids, conjugate addition reactions, and enolate anion reactions and condensation reactions that lead to non-α-amino acids. It also examines reactions and strategies that lead to good diastereoselectivity and enantioselectivity during synthesis. A chapter devoted to biologically important amino acids includes separate sections on GABA, GABOB, carnitine, DAVA, statine, and other significant amino acids as well as a new section on peptides and proteins that contain non-α-amino acids. The final chapter addresses aminocyclic and heterocyclic amino acids.

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Product Details

  • ISBN-13: 9781466577893
  • Publisher: CRC Press
  • Publication date: 11/6/2013
  • Edition description: Revised
  • Edition number: 2
  • Pages: 242
  • Product dimensions: 6.20 (w) x 9.20 (h) x 0.70 (d)

Meet the Author

Michael B. Smith attended Purdue University, graduating with a Ph.D. in Organic Chemistry. His postdoctoral work took place at the Arizona State University with George R. Pettit and at the Massachusetts Institute of Technology with Sidney Hecht. Dr. Smith joined the faculty at the University of Connecticut in 1977, where he now holds the rank of full professor. He is the author of the 5th–7th editions of March's Advanced Organic Chemistry, Organic Synthesis (3rd edition), and Organic Chemistry: An Acid-Base Approach.

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Table of Contents

Functional Group Exchanges
Reactions with Ammonia, Amines, or Amine Surrogates
Conversion of Carbonyl Compounds to Amines
Refunctionalization to Generate Carboxyl Groups
Refunctionalization of Amino Acids
Specialized Methods

Cyclic Precursors
From Lactams or Imides
From Ketones
From Lactones and Anhydrides
From Heterocycles
Diels-Alder Strategies

Conjugate Addition Reactions
Ammonia and Amine Nucleophiles
Carbon Nucleophiles

Enolate Anion and Related Reactions
Acid, Ester, and Malonate Enolate Anion Reactions
Nitrile Enolate Anions
Nitroalkane Enolate Anions
Mukaiyama Type Condensations
Condensation Reactions Involving Organozinc Intermediates
Ylid Reactions

Diastereoselective and Enantioselective Syntheses
α-Amino Acid Templates Non-α-Amino Acid Templates Synthesis From Other Starting Materials
Transformations Using Carbohydrates as Chiral Templates
Enzymatic Transformations

Biologically Important Amino Acids
Peptides and Proteins
β-Alanine and Aminopropanoic Acid Compounds
GABA and Related Compounds
GABOB and Carnitine
DAVA (Ava) and Ahx
Statine and Related Compounds
Other Biologically Important Amino Acid Derivatives
Non-α-Amino Acids in Catalysis

Aminocyclic and Heterocyclic Amino Acids
Aminocycloalkylcarboxylic Acids From Cyclic Precursors
From Aromatic Precursors
From Cyclic Ketones
Cycloaddition Strategies
Heteroatom Cyclic Amino Acids

Index

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