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Issue 39, 2020

Total synthesis of biseokeaniamides A–C and late-stage electrochemically-enabled peptide analogue synthesis

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Abstract

The first total synthesis of cytotoxic cyanobacterial peptide natural products biseokeaniamides A–C is reported employing a robust solid-phase approach to peptide backbone construction followed by coupling of a key thiazole building block. To rapidly access natural product analogues, we have optimized an operationally simple electrochemical oxidative decarboxylation–nucleophilic addition pathway which exploits the reactivity of native C-terminal peptide carboxylates and abrogates the need for building block syntheses. Electrochemically-generated N,O-acetal intermediates are engaged with electron-rich aromatics and organometallic reagents to forge modified amino acids and peptides. The value of this late-stage modification method is highlighted by the expedient and divergent production of bioactive peptide analogues, including compounds which exhibit enhanced cytotoxicity relative to the biseokeaniamide natural products.

Graphical abstract: Total synthesis of biseokeaniamides A–C and late-stage electrochemically-enabled peptide analogue synthesis

Supplementary files

Article information


Submitted
06 Jul 2020
Accepted
29 Jul 2020
First published
30 Jul 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 10752-10758
Article type
Edge Article

Total synthesis of biseokeaniamides A–C and late-stage electrochemically-enabled peptide analogue synthesis

Y. Lin and L. R. Malins, Chem. Sci., 2020, 11, 10752 DOI: 10.1039/D0SC03701J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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