Tryptophan N ¹-Alkylation: Quick and Simple Access to Diversely Substituted Tryptophans

Abstract

The diversification of amino acid sidechains is a major challenge in the synthesis and derivatization of peptides for pharmaceutical applications. We herein present a new protocol to alkylate the indole-nitrogen (N1) of N ^α-protected tryptophans. This method provides quick and epimerization-free access to tryptophan derivatives, which can directly be incorporated into peptides. Depending on the functionalities introduced in the side chain, different options for the late-stage modification of peptides are possible.

Key words

tryptophan - N-alkylation - amino acids - late-stage diversification - peptide modification

Publikationsverlauf

Eingereicht: 11. Februar 2021

Angenommen: 03. März 2021

Accepted Manuscript online:
03. März 2021

Artikel online veröffentlicht:
16. März 2021

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