Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis

[Image: see text] α-Formylglycine (fGly) is a rare residue located in the active site of sulfatases and serves as a precursor to pharmaceutically relevant motifs. The installation of fGly motifs into peptides is currently challenging due to degradation under the acidic and nucleophile-rich condition...

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Autores principales: Yates, Nicholas D. J., Warnes, Matthew E., Breetveld, Reuben, Spicer, Christopher D., Signoret, Nathalie, Fascione, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10071478/
https://www.ncbi.nlm.nih.gov/pubmed/36662590
http://dx.doi.org/10.1021/acs.orglett.2c04059
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author Yates, Nicholas D. J.
Warnes, Matthew E.
Breetveld, Reuben
Spicer, Christopher D.
Signoret, Nathalie
Fascione, Martin
author_facet Yates, Nicholas D. J.
Warnes, Matthew E.
Breetveld, Reuben
Spicer, Christopher D.
Signoret, Nathalie
Fascione, Martin
author_sort Yates, Nicholas D. J.
collection PubMed
description [Image: see text] α-Formylglycine (fGly) is a rare residue located in the active site of sulfatases and serves as a precursor to pharmaceutically relevant motifs. The installation of fGly motifs into peptides is currently challenging due to degradation under the acidic and nucleophile-rich conditions accompanying resin cleavage during solid-phase peptide synthesis. We report the synthesis of acid- and nucleophile-tolerant α-formylglycine building blocks from vitamin C and use them to prepare callyaerin A, a macrocyclic peptide containing an fGly-derived motif.
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spelling pubmed-100714782023-04-05 Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis Yates, Nicholas D. J. Warnes, Matthew E. Breetveld, Reuben Spicer, Christopher D. Signoret, Nathalie Fascione, Martin Org Lett [Image: see text] α-Formylglycine (fGly) is a rare residue located in the active site of sulfatases and serves as a precursor to pharmaceutically relevant motifs. The installation of fGly motifs into peptides is currently challenging due to degradation under the acidic and nucleophile-rich conditions accompanying resin cleavage during solid-phase peptide synthesis. We report the synthesis of acid- and nucleophile-tolerant α-formylglycine building blocks from vitamin C and use them to prepare callyaerin A, a macrocyclic peptide containing an fGly-derived motif. American Chemical Society 2023-01-20 /pmc/articles/PMC10071478/ /pubmed/36662590 http://dx.doi.org/10.1021/acs.orglett.2c04059 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Yates, Nicholas D. J.
Warnes, Matthew E.
Breetveld, Reuben
Spicer, Christopher D.
Signoret, Nathalie
Fascione, Martin
Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
title Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
title_full Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
title_fullStr Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
title_full_unstemmed Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
title_short Preparation and Application of an Inexpensive α-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
title_sort preparation and application of an inexpensive α-formylglycine building block compatible with fmoc solid-phase peptide synthesis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10071478/
https://www.ncbi.nlm.nih.gov/pubmed/36662590
http://dx.doi.org/10.1021/acs.orglett.2c04059
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