Amino Acids, Peptides and Proteins in Organic Chemistry: Volume 4 - Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis / Edition 1

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Closing a gap in the literature, this is the only book series in 6 volumes to cover this important topic in organic and biochemistry. Drawing upon the combined expertise of the international "who's who" in amino acid research, this series is 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.

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Product Details

Meet the Author

Andrew Hughes is a reader and Head of the Department of Chemistry, La Trobe University, Melbourne, Australia. He obtained his degrees from the University of Western Australia. Post-doctoral appointments at the University of Cambridge starting 1989 included 3 years working with Professor Andrew Holmes before joining Professor Steven Ley's group in 1993. While at Cambridge he was appointed the Shell Research Fellow at Robinson College.

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Table of Contents

List of Contributors.

1 Protection Reactions (Vommina V. Sureshbabu andNarasimhamurthy Narendra ).

1.1 General Considerations.

1.2 α-Amino Protection(Nα Protection).

1.3 Carboxy Protection.

1.4 Side-Chain Protection.

1.5 Photocleavable Protections.

1.6 Conclusions.

1.7 Experimental Procedures.


Part One Amino Acid-Based Peptidomimetics.

2 Huisgen Cycloaddition in Peptidomimetic Chemistry(Daniel Sejer Pedersen and Andrew David Abell ).

2.1 Introduction.

2.2 Huisgen [2 + 3] Cycloaddition Between Azides andAcetylenes.

2.3 Mechanistic Consideration for the Cu-Huisgen and Ru-HuisgenCycloadditions.

2.4 Building Blocks for the Synthesis of Triazole-ModifiedPeptidomimetics.

2.5 Cyclic Triazole Peptidomimetics.

2.6 Acyclic Triazole Peptidomimetics.

2.7 Useful Experimental Procedures.


3 Recent Advances in ß-Strand Mimetics (Wendy A.Loughlin and David P. Fairlie ).

3.1 Introduction.

3.2 Macrocyclic Peptidomimetics.

3.3 Acyclic Compounds.

3.4 Aliphatic and Aromatic Carbocycles.

3.5 Ligands Containing One Ring with One Heteroatom (N).

3.6 Ligands Containing One or Multiple Rings with One Heteroatom(O, S).

3.7 Ligands Containing One Ring with Two Heteroatoms (N,N).

3.8 Ligands Containing One Ring with Two Heteroatoms (N,S) orThree Heteroatoms (N,N,S or N,N,N).

3.9 Ligands Containing Two Rings with One Heteroatom (N orO).

3.10 Ligands Containing Two Rings with Two or Three Heteroatoms(N,N or N,S or N,N,N).

3.11 Conclusions.


Part Two Medicinal Chemistry of Amino Acids.

4 Medicinal Chemistry of α-Amino Acids (LennartBunch and Povl Krogsgaard-Larsen ).

4.1 Introduction.

4.2 Glutamic Acid.

4.3 Conformational Restriction.

4.4 Bioisosterism,

4.5 Structure–Activity Studies.

4.6 Conclusions.


5 Medicinal Chemistry of Alicyclic ß-Amino Acids(Nils Griebenow ).

5.1 Introduction.

5.2 Five-Membered Alicyclic ß-Amino Acids.

5.3 Six-Membered Alicyclic ß-Amino Acids.


6 Medicinal Chemistry of a-Hydroxy-ß-Amino Acids(Zyta Ziora, Mariusz Skwarczynski, and Yoshiaki Kiso ).

6.1 Introduction.

6.2 α-Hydroxy-ß-Amino Acids.

6.3 Antibacterial Agents.

6.4 Inhibitors of Aminopeptidases.

6.5 Aspartyl Proteases Inhibitors.

6.6 Paclitaxel and its Derivatives.


7 Peptide Drugs (Chiara Falciani, Alessandro Pini, andLuisa Bracci ).

7.1 Lights and Shades of Peptide and Protein Drugs.

7.2 Peptide Drugs Available on the Market.

7.3 Approved Peptides in Oncology.

7.4 Antimicrobial peptides.

7.5 Perspectives.


8 Oral Bioavailability of Peptide and PeptidomimeticDrugs (Arik Dahan, Yasuhiro Tsume, Jing Sun, Jonathan M.Miller, and Gordon L. Amidon ).

8.1 Introduction.

8.2 Fundamental Considerations of Intestinal Absorption.

8.3 Barriers Limiting Oral Peptide/Peptidomimetic DrugBioavailability.

8.4 Strategies to Improve Oral Bioavailability of Peptide-BasedDrugs.

8.5 Conclusions.


9 Asymmetric Synthesis of ß-Lactams via the StaudingerReaction (Monika I. Konaklieva and Balbina J. Plotkin).

9.1 Introduction.

9.2 Staudinger Reaction.

9.3 Influence of the Geometry of the Imine on Stereoselectivityin the Reaction.

9.4 Influence of the Polarity of the Solvent onStereoselectivity of the Reaction.

9.5 Influence of the Isomerization of the Imine Prior to itsNucleophilic Attack onto the Ketene Stereoselectivity in theReaction.

9.6 Influence of the Order of Addition of the Reactants to theReaction.

9.7 Influence of Chiral Substituents on the Stereoselectivity ofthe Reaction.

9.8 Asymmetric Induction from the Imine Component.

9.9 Asymmetric Induction from the Ketene Component.

9.10 Double Asymmetric Cycloinduction.

9.11 Influence of Catalysts on the Stereoselectivity of theReaction.

9.12 Conclusions.


10 Advances in N- and O-Glycopeptide Synthesis – A Toolto Study Glycosylation and Develop New Therapeutics (UlrikaWesterlind and Horst Kunz ).

10.1 Introduction.

10.2 Synthesis of O-Glycopeptides.

10.3 Synthesis of N-Glycopeptides.


11 Recent Developments in Neoglycopeptide Synthesis(Margaret A. Brimble, Nicole Miller, and Geoffrey M.Williams ).

11.1 Introduction.

11.2 Neoglycoside and Neoglycopeptide Synthesis.

11.3 Protein Side-Chain Modifications.

11.4 Cu(I)-Catalyzed Azide–Alkyne‘‘Click’’ Cycloaddition.

11.5 Cross-Metathesis.

11.6 Application of Neoglycopeptides as Synthetic Vaccines.

11.7 Enzymatic, Molecular, and Cell Biological Techniques.


Part Three Amino Acids in Combinatorial Synthesis.

12 Combinatorial/Library Peptide Synthesis (MichalLebl ).

12.1 Introduction.

12.2 High-Throughput Synthesis of Peptides.

12.3 Synthesis of Peptide Arrays.

12.4 Peptide Libraries.

12.5 Future of Peptide Libraries.

12.6 Synthetic Protocols.


13 Phage-Displayed Combinatorial Peptides (RenhuaHuang, Kritika Pershad, Malgorzata Kokoszka, and Brian K. Kay).

13.1 Introduction.

13.2 Conclusions.


14 Designing New Proteins (Michael I. Sadowski andJames T. MacDonald ).

14.1 Introduction.

14.2 Protein Design Methods.

14.3 Protocol for Protein Design.

14.4 Conclusions.


15 Amino Acid-Based Dendrimers (Zhengshuang Shi,Chunhui Zhou, Zhigang Liu, Filbert Totsingan, and Neville R.Kallenbach ).

15.1 Introduction.

15.2 Peptide Dendrimer Synthesis: Divergent and ConvergentApproaches.

15.3 Applications of Peptide Dendrimers.

15.4 Conclusions.



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