The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and CyclizationReportar como inadecuado


The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization


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1

Research Group of Organic Chemistry, Departments of Bioengineering Sciences and Chemistry, Vrije Universiteit Brussel, 1050 Brussels, Belgium

2

Organic Synthesis Division, University of Antwerp, 2020 Antwerp, Belgium

3

Discovery Sciences, Janssen Research and Development, 2340 Beerse, Belgium





*

Author to whom correspondence should be addressed.



Academic Editor: Ioannis D. Kostas

Abstract The site-selective derivatization of amino acids and peptides represents an attractive field with potential applications in the establishment of structure–activity relationships and labeling of bioactive compounds. In this respect, bioorthogonal cross-coupling reactions provide valuable means for ready access to peptide analogues with diversified structure and function. Due to the complex and chiral nature of peptides, mild reaction conditions are preferred; hence, a suitable cross-coupling reaction is required for the chemical modification of these challenging substrates. The Suzuki reaction, involving organoboron species, is appropriate given the stability and environmentally benign nature of these reactants and their amenability to be applied in partial aqueous reaction conditions, an expected requirement upon the derivatization of peptides. Concerning the halogenated reaction partner, residues bearing halogen moieties can either be introduced directly as halogenated amino acids during solid-phase peptide synthesis SPPS or genetically encoded into larger proteins. A reversed approach building in boron in the peptidic backbone is also possible. Furthermore, based on this complementarity, cyclic peptides can be prepared by halogenation, and borylation of two amino acid side chains present within the same peptidic substrate. Here, the Suzuki–Miyaura reaction is a tool to induce the desired cyclization. In this review, we discuss diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction. With the advent of peptide-based drugs, versatile bioorthogonal conversions on these substrates have become highly valuable. View Full-Text

Keywords: Suzuki–Miyaura reaction; peptide diversification; peptide cyclization Suzuki–Miyaura reaction; peptide diversification; peptide cyclization





Autor: Tom Willemse 1,2, Wim Schepens 3, Herman W. T. van Vlijmen 3, Bert U. W. Maes 2 and Steven Ballet 1,*

Fuente: http://mdpi.com/



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