Synthesis of Peptide N-Acylpyrroles via Anodically Generated N,O-Acetals

Date

2022-05-09

Authors

Malins, Lara
Lin, Yutong

Journal Title

Journal ISSN

Volume Title

Publisher

Thieme Gruppe

Abstract

An electrochemical approach to peptide C-terminal N-acylpyrroles is described from readily accessible C-terminal hydroxyproline-containing peptides, prepared via standard Fmoc solid-phase peptide synthesis (Fmoc-SPPS). Following electrochemical decarboxylation, the reactive hydroxyproline-derived N,O-acetal intermediate is aromatized under mild acidic conditions, which enable concomitant deprotection of amino acid side-chain protecting groups. The resulting peptide N-acylpyrrole is amenable to late-stage peptide modifications, including reduction with NaBH4 to deliver a valuable C-terminal peptide aldehyde motif.

Description

Keywords

decarboxylation, electrochemistry, anodic oxidation, aromatization, N-acylpyrrole, late-stage modification, C-terminal modification

Citation

Source

Synthesis

Type

Journal article

Book Title

Entity type

Access Statement

Open Access

License Rights

DOI

10.1055/s-0041-1737411

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