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Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

ABSTRACT: 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.

SUBMITTER: Dachwitz S

PROVIDER: S-EPMC9299634 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Dachwitz Steffen S Scharkowski Bjarne B Sewald Norbert N

Chemistry (Weinheim an der Bergstrasse, Germany) 20211111 72

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 p ...[more]

PMID: 34713938

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