Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Steffen Dachwitz, Bjarne Scharkowski, Norbert Sewald

Chemistry (Weinheim an der Bergstrasse, Germany) 2021 Dec 23

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Mild transition-metal catalysed cross-couplings enable direct functionalisation of biocatalytically halogenated tryptophans with alkyl iodides, representing a new alternative for late-stage derivatisations of halogenated aromatic amino acids. Moreover, this strategy enables preparation of (homo)tryptophan regioisomers in a simple two-step synthesis using a Pd-catalysed Negishi cross coupling. This method provides access to non-canonical constitutional surrogates of tryptophan, ready for use in peptide synthesis. © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Citation

Steffen Dachwitz, Bjarne Scharkowski, Norbert Sewald. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers. Chemistry (Weinheim an der Bergstrasse, Germany). 2021 Dec 23;27(72):18043-18046