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Lin Y, Malins LR. An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes. J Am Chem Soc. 2021;143(30):11811-11819doi: 10.1021/jacs.1c05718.
Lin, Y., & Malins, L. R. (2021). An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes. Journal of the American Chemical Society, 143(30), 11811-11819. https://doi.org/10.1021/jacs.1c05718
Lin, Yutong, and Malins, Lara R. "An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes." Journal of the American Chemical Society vol. 143,30 (2021): 11811-11819. doi: https://doi.org/10.1021/jacs.1c05718
Lin Y, Malins LR. An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes. J Am Chem Soc. 2021 Aug 04;143(30):11811-11819. doi: 10.1021/jacs.1c05718. Epub 2021 Jul 21. PMID: 34288681.
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J Am Chem Soc. 2021 Aug 04;143(30):11811-11819. doi: 10.1021/jacs.1c05718. Epub 2021 Jul 21.

An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes.

Journal of the American Chemical Society

Yutong Lin, Lara R Malins

Affiliations

  1. Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia.
  2. Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, Australian National University, Canberra, ACT 2601, Australia.

PMID: 34288681 DOI: 10.1021/jacs.1c05718

Abstract

Designer C-terminal peptide amides are accessed in an efficient and epimerization-free approach by pairing an electrochemical oxidative decarboxylation with a tandem hydrolysis/reduction pathway. Resembling Nature's dual enzymatic approach to bioactive primary α-amides, this method delivers secondary and tertiary amides bearing high-value functional motifs, including isotope labels and handles for bioconjugation. The protocol leverages the inherent reactivity of C-terminal carboxylates, is compatible with the vast majority of proteinogenic functional groups, and proceeds in the absence of epimerization, thus addressing major limitations associated with conventional coupling-based approaches. The utility of the method is exemplified through the synthesis of natural product acidiphilamide A

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