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Techniques for the Facilitation of Peptide Synthesis

  • Chapter
Principles of Peptide Synthesis

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 16))

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Abstract

Synthesis of a peptide chain comprising a large number of amino acid residues can be a difficult task and proteins with over a hundred and sometimes hundreds of residues are formidable objectives. The steps of protection, coupling, deprotection, isolation and characterization of the intermediates - is not only a time consuming but also adiscouragingly repetitive endeavor. An additional source of frustration is the scarcity of solvents which are suitable for reactions with high molecular weight intermediates. Such difficulties lead to a search for techniques which can alleviate the burden of peptide chemists, for methods which can facilitate the building of long peptide chains from amino acids. The repetitive character of chain lengthening with active esters prompted speculations [1] about the mechanization of peptide synthesis. The first realization of such ideas came from Merrifield [2] and, simultaneously, from Letsinger and Körnet [3]. In both methods an amino acid is attached to an insoluble polymeric support and the subsequent operations are carried out on the peptidic material linked to the resin. The version proposed by Merrifield [2] developed into a major discipline, solid phase peptide synthesis. One of the most conspicuous characteristics of the new technique is that it stimulated further thoughts toward improvements and analogous solutions to an unprecedented extent. Research grew in this area in an exponential manner and has been reviewed repeatedly. A recent, comprehensive review of solid phase peptide synthesis by Barany and Merrifield [4] required almost 300 pages for a full account. The “solid” phase idea permeated other fields as well and is used now, with success, in the sequencing of proteins and in the synthesis of oligo- and polynucleotides. In this chapter we can give only the outlines of solid phase peptide synthesis particularly because it seems to be necessary to discuss in this connection also alternative techniques of facilitation even if these do not match in importance the solid phase method, at this time.

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  1. Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA

    Miklos Bodanszky

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Bodanszky, M. (1984). Techniques for the Facilitation of Peptide Synthesis. In: Principles of Peptide Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 16. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-96763-4_7

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  • DOI: https://doi.org/10.1007/978-3-642-96763-4_7

  • Publisher Name: Springer, Berlin, Heidelberg

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