A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides

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2019
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Keiper, Odin
Unverzagt, Carlo
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Chemistry - A European Journal. 2019, 25(69), pp. 15759-15764. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201904688
Zusammenfassung

A general and robust method for the incorporation of aspartates with a thioacid side chain into peptides has been developed. Pseudoproline tripeptides served as building blocks for the efficient Fmoc solid-phase synthesis of thioacid-containing peptides. These peptides were readily converted to complex N-glycopeptides using a fast and chemoselective one-pot deprotection/ligation procedure. Furthermore, a novel side reaction leading to site-selective peptide cleavage using thioacids (CUT) was discovered and studied in detail.

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540 Chemie
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ISO 690SCHÖWE, Markus Julian, Odin KEIPER, Carlo UNVERZAGT, Valentin WITTMANN, 2019. A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides. In: Chemistry - A European Journal. 2019, 25(69), pp. 15759-15764. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201904688
BibTex
@article{Schowe2019-10-19Tripe-47278,
  year={2019},
  doi={10.1002/chem.201904688},
  title={A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides},
  number={69},
  volume={25},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={15759--15764},
  author={Schöwe, Markus Julian and Keiper, Odin and Unverzagt, Carlo and Wittmann, Valentin}
}
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