Handbook on Syntheses of Amino Acids: General Routes to Amino Acids - Rilegato

Blaskovich, Mark A.

Rilegato

ISBN 10: 0841272190 ISBN 13: 9780841272194

Casa editrice: OUP USA, 2010

Riassunto

Amino acid synthesis is a field of research that has existed for over 150 years, but renewed interest has led to an exponential increase in publications in the past two decades. The Handbook on Syntheses of Amino Acids provides a comprehensive survey of synthetic procedures that prepare natural and unnatural amino acids in both racemic and optically active forms. The book begins with an introduction to amino acids, their properties, and anylytical techniques, including a detailed examination of methods used to establish enantiomeric configuration and optical purity. The next two chapters focus on processes for preparing racemic amino acids, dividing into those syntheses that introduce the amino and/or carboxy groups, and those that introduce the side chain. While some of these procedures date from the 1800s, modified versions are still extensively employed. A key component of these chapters is tables that summarize that summarize the many compounds made by each method. A chapter devoted to 2, 3-dehydroamino acids provides the bridge between racemic and asymmetric syntheses, as dehydroamino acids are themselvces achiral, but can be transformed into optically active products. Asymmetric amino acid preparations are then divided into six chapters, based on methods that introduce the amino and/or carboxy groups, those that introduce the side chains to acyclic synthons, those that introduce side chain to cyclic templates, those that open small ring systems, and those that derive the amino acided from other amino acids (with a separate chapter for serine-derived products). The growing field of non-?-amino acid synthesis is adressed in a separate chapter . The book is completed by a discussion of amino acids, including resolutions, N-alkylations, amidations and peptide couplings.

Su questo libro

L'autore:

Mark Blaskovich is Chief Operating Officer at Mimetica, a peptidomimetic drug discovery company. An experienced industrial medicinal chemist, Mark has worked for CEPTYR Inc and the former peptide mimetics company Molecumetics.

Contenuti:

• Chapter 1. Introduction
• 1.1: General Introduction
• 1,2: A Brief Summary of Trends in Amino Acid Synthesis
• 1.3: Industrial Synthesis
• 1.4: Amino Acid Properties
• 1.5: Absolute Configuration
• 1.6: Determination of Enantiomeric Purity
• 1.7: Determination of Enantiomeric Purity: NMR Analysis
• 1.8: Determination of Enantiomeric Purity: HPLC Chromatographic Analysis
• 1.9: Determination of Enantiomeric Purity: GC Chromatographic Analysis
• 1.10: Determination of Enantiomeric Purity: Capillary Electrophoresis Analysis
• 1.11: Determination of Enantiomeric Purity: TLC Chromatographic Analysis
• 1.12: Determination of Enantiomeric Purity: Mass Spectrometric Methods
• 1.13: Determination of Enantiomeric Purity: Other Methods
• Chapter 2. Synthesis of Racemic a-Amino Acids: Amination and Carboxylation
• 2.1: Primordial Amino Acids
• 2.2: Addition of the Amino and Carboxy Groups to the Side Chain (Aminocarboxylation Reactions)
• 2.3: Addition of the Amino Group (Amination Reactions)
• 2.4: Addition of the Carboxyl Group (Carboxylation Reactions)
• 2.4.1: Electrophilic Carboxylation
• 2.4.2: Nucleophilic Carboxylation
• Chapter 3. Synthesis of Racemic -Amino Acids: Introduction of the Side Chain
• 3.1: Introduction
• 3.2: Alkylation of Aminomalonic Acids
• 3.3: Alkylation of Aminocyanoacetic Acids
• 3.4: Alkylation of Schiff Bases
• 3.5: Alkylation of Isocyanoacetates
• 3.6: Alkylation of Other Activated Glycine Equivalents
• 3.7: Alkylation of Non-Activated Glycines
• 3.8: Alkylation of Glycine Equivalents via Other Methods
• 3.9: Alkylation of an Electrophilic Glycine Equivalent
• 3. 10: Radical Alkylations
• Chapter 4. Synthesis and Elaboration of Didehydro Amino Acids
• 4.1: Introduction
• 4.2: Sythesis of Didehydroamino Acids
• 4.3: Reactions of Didehydroamino Acids
• Chapter 5. Synthesis of Optically Active a-Amino Acids: Extension of Achiral Methods - Amination and Carboxylation Reactions
• 5.1: Introduction
• 5.2: Asymmetric Aminocarboxylation Reaction
• 5.3: Asymmetric Amination Reactions
• 5.4: Asymmetric Carboxylation Reactions
• Chapter 6. Synthesis of Optically Active Amino Acids: Extension of Achiral Methods - Introduction fo the Side Chain to Acyclic Systems
• 6.1: Introduction
• 6.2: Asymmetric Alkylations of Glycine Enolates
• 6.3: Reactions of Isocyanocarboxylate Enolates
• 6.4: Alkylations of Schiff Bases of Glycine or Other Amino Acids
• 6.5: Asymmetric Alkylations of Electrophilic Glycine Equivalents
• 6.6: Asymmetric Radical Alkylations of Acyclic Glycine Equivalents
• Chapter 7. Synthesis of Optically Active a-Amino Acids: Alkylation of Cyclic Chiral Templates
• 7.1: Introduction
• 7.2: Schöllkopf Bis-lactim Ether
• 7.3: Piperazine-2,5-dione
• 7.4: Morpholine-2,5-dione
• 7.5: Williams Oxazinone (5,6-diphenyl-1,4-oxazin-2-one, 5,6-diphenylmorpholin-2-one)
• 7.6: Other Oxazinones (1,4-oxazin-2-one, morpholin-2-one)
• 7.7: Seebach Oxazolidin-5-one
• 7.8: Oxazolidin-2-ones
• 7.9: Seebach Imidazolidin-4-one
• 7.10: Other Imidazolidinones and Related Templates
• 7.11: Cyclic Metal Complexes
• 7.12: Other Cyclic Chiral Templates
• Chapter 8. Synthesis of Optically Active a-Amino Acids: Opening of Small Ring Systems
• 8.1: Introduction
• 8.2: Aziridines
• 8.3: Azirines
• 8.4: Epoxides
• 8.5: b-Lactams
• Chapter 9. Synthesis of Optically Active a-Amino Acids: Elaboration of Amino Acids Other than Serine
• 9.1: Introduction
• 9.2: Synthesis of Optically Active Amino Acids from Aspartic Acid
• 9.3: Synthesis of Optically Active Amino Acids from Glutamic Acid
• 9.4: Synthesis of Optically Active Amino Acids from Asparagine/Glutamine
• 9.5: Syntheses from Other Amino Acids
• Chapter 10. Synthesis of Optically Active -Amino Acids: Elaboration of Serine
• 10.1: Introduction
• 10.2: Racemization of Serine
• 10.3: Nucleophilic Displacement of an Activated Serine Hydroxyl Group
• 10.4: Radical Reactions
• 10.5: Nucleophilic Alaninol Synthons Derived from Serine
• 10.6: Serine Aldehydes: Conversion of the Serine Carboxyl Group into an Aldehyde/Ketone
• 10.7: Serine Aldehydes: Conversion of the Serine Side Chain Hydroxyl Group into an Aldehyde
• 10.8: Other Reactions of Serine
• Chapter 11. Synthesis of -, -, -, and -Amino Acids
• 11.1: Introduction
• 11.2: b-Amino Acids
• 11.3: Cyclic b-Amino Acids
• 11.4: y-Amino Acids
• 11.5: Cyclic y-Amino Acids
• 11.6: -Amino Acids
• 11.7: Cyclic -Amino Acids
• 11.8: -Amino Acids
• Chapter 12. Modifications of Amino Acids: Resolution, N-Alkylation, N-Protection, Amidation and Coupling
• 12.1: Resolutions of a-Amino Acids
• 12.2: N-Alkylation of Amino Acids
• 12.3: N-Acylation and N-Protection of Amino Acids
• 12.4: Amidation and Amide Hydrolysis
• 12.5: Coupling of Amino Acids

Su questa edizione

• Editore: OUP USA
• Data di pubblicazione: 2010
• ISBN 10: 0841272190
• ISBN 13: 9780841272194
• Rilegatura: Copertina rigida
• Numero di pagine: 1328