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Peptide Synthesis 7. Summary and Outlook

Author:N/A    | Post time:2012-05-26

7. Summary and Outlook
Top of page
1. Introduction
2. Fundamentals of Peptide Synthesis
3. Strategies for Peptide Synthesis
4. Chain-Growing and Side-Chain Protective Groups
5. Coupling Methods
6. Side Reactions
7. Summary and Outlook
More than 40 years after Merrifield\'s ingenious invention of solid phase peptide synthesis, this technology has matured into a multi million Dollar business. However, especially when compared to oligonucleotide synthesis, peptides are still quite expensive, and, due to the low repetitive coupling yield during chemical synthesis, the length of standard peptides is restricted to <50 amino acids. The performance of Nature\'s ribosomes is much better in this respect, which gives the ribosome-based methods a competitive edge over chemical methods in the synthesis of large peptides and proteins. Despite these drawbacks that somehow limited the use of peptides in science and industry, more and more peptides made their way into the clinics. This is partially due to the big advantage of chemical synthesis over biology-based methods: Chemical synthesis methods can incorporate non-natural building blocks into a peptide chain. To mention a few: d-amino acids would shield a peptide from proteolysis inside the body – a feature that should help in the development of peptide-based therapeutics. Other building blocks could be used to monitor the peptide and its binding partner, e.g. by fluorescence inside a cell or as a contrast agent inside the body. The incorporation of catalytic centers directly into the peptide might yield novel catalysts, where, similar to Nature, the peptide contributes specific binding to the transitional state.
For most of these applications a binding peptide must be found in the first place, with the array format providing the most convenient screening technique. Many examples of this kind are already available from SPOT synthesis studies, although this technique is limited to a few thousand peptides per experiment. By contrast, arrays with hundreds of thousands of oligonucleotides are now routinely used to screen whole genomes, and, thus, revolutionized the field of “genomics”. The recent development of high-density peptide arrays might boost the field of “proteomics” in a similar way. Such arrays will probably speed up the search for small ligands that, e.g., block an intracellular signalling pathway by binding to a target protein. An array with >20.000 different peptides should present enough 3D structures to identify low affinity binders for almost any protein structure that is used as a probe in initial screens. Starting from initial peptide “hits”, iterative screens with peptide variants should yield high-affinity binders with unprecedented speed. Finally, if we learn to synthesize peptides in high density, release them from solid supports in the array format, and consecutively incorporate faithfully synthesized peptides from several such arrays into a well-defined 3D architecture, then we might even generate structures that behave similar to proteins. One day, such arrays might allow for screening of very sophisticated properties. Then, screening for peptide-based catalysts or photosystem-inspired molecular semiconductors may no longer be a mere dream.
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Further Reading
S. E. Blondelle (ed.): Understanding Biology Using Peptides, Springer, New York, NY 2006.
A. M. Boldi (ed.): Combinatorial Synthesis of Natural Product-Based Libraries, CRC/Taylor & Francis, Boca Raton, FL 2006.
S. Br se (ed.): Combinatorial Chemistry on Solid Supports, Springer, Berlin 2007.
J. S. Davies, G. C. Barrett (eds.): Amino Acids, Peptides and Proteins, Royal Society of Chemistry, Cambridge, UK 2010.
B. Groner (ed.): Peptides as Drugs, Wiley-VCH, Weinheim 2009.
H.-D. Jakubke, N. Sewald: Peptides from A to Z, Wiley-VCH, Weinheim 2008.
CrossRef
K. J. Jensen (ed.): Peptide and Protein Design for Biopharmaceutical Applications, Wiley, Chichester 2009.
P. J. H. Scott (ed.): Linker Strategies in Solid-Phase Organic Synthesis, Wiley, Hoboken, NJ 2009.
N. Sewald, H.-D. Jakubke: Peptides: Chemistry and Biology, 2nd ed., Wiley-VCH, Weinheim 2009.
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P. G. M. Wuts, T. W. Greene: Greene\'s Protective Groups in Organic Synthesis, 4th ed., Wiley, Hoboken, NJ 2007.

 

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