Yates, Nicholas D.J., Warnes, Matthew E., Breetveld, Reuben et al. (3 more authors) (2023) Preparation and Application of an Inexpensive α‐Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis. Organic Letters. ISSN 1523-7052
Abstract
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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Copyright, Publisher and Additional Information: | Funding Information: We thank Dr. Ed Bergstrom and The York Centre of Excellence in Mass Spectrometry. The York Centre of Excellence in Mass Spectrometry was created thanks to a major capital investment through Science City York, supported by Yorkshire Forward with funds from the Northern Way Initiative, and subsequent support from EPSRC (EP/K039660/1; EP/M028127/1). This work was supported by The University of York, the EPSRC (summer vacation bursary for M.E.W. and EP/V044303/1) and UKRI (EP/X023680/1). Publisher Copyright: © 2023 The Authors. Published by American Chemical Society. | ||||||
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Institution: | The University of York | ||||||
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) The University of York > Faculty of Sciences (York) > Hull York Medical School (York) |
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Funding Information: |
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Depositing User: | Pure (York) | ||||||
Date Deposited: | 23 Jan 2023 11:40 | ||||||
Last Modified: | 20 Feb 2024 00:19 | ||||||
Published Version: | https://doi.org/10.1021/acs.orglett.2c04059 | ||||||
Status: | Published online | ||||||
Refereed: | Yes | ||||||
Identification Number: | https://doi.org/10.1021/acs.orglett.2c04059 | ||||||
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