Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 24, Pages 5328-5340Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903756
Keywords
cross-coupling; enzymatic halogenation; late-stage diversification; palladium catalysis; tryptophans
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Funding
- Deutsche Forschungsgemeinschaft [SE 609/16-1]
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Pd-mediated reactions have emerged as a powerful tool for the site-selective and bioorthogonal late-stage diversification of amino acids, peptides and related compounds. Indole moieties of tryptophan derivatives are susceptible to (CH)-H-2-activation, whereas halogenated aromatic amino acids such as halophenylalanines or halotryptophans provide a broad spectrum of different functionalisations. The compatibility of transition-metal-catalysed cross-couplings with functional groups in peptides, other biologically active compounds and even proteins has been demonstrated. This Review primarily compiles the application of different cross-coupling reactions to modify halotryptophans, halotryptophan containing peptides or halogenated, biologically active compounds derived from tryptophan. Modern approaches use regio- and stereoselective biocatalytic strategies to generate halotryptophans and derivatives on a preparative scale. The combination of bio- and chemocatalysis in cascade reactions is given by the biocompatibility and bioorthogonality of Pd-mediated reactions.
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