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

ABSTRACT: 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 fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of thioacid-containing peptides. These peptides were readily converted to complex N-glycopeptides by using a fast and chemoselective one-pot deprotection/ligation procedure. Furthermore, a novel side reaction that can lead to site-selective peptide cleavage using thioacids (CUT) was discovered and studied in detail.

SUBMITTER: Schowe MJ

PROVIDER: S-EPMC6916195 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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

Schöwe Markus Julian MJ Keiper Odin O Unverzagt Carlo C Wittmann Valentin V

Chemistry (Weinheim an der Bergstrasse, Germany) 20191107 69

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 fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of thioacid-containing peptides. These peptides were readily converted to complex N-glycopeptides by using a fast and chemoselective one-pot deprotection/ligation procedure. Furthermore, a novel side reaction that can lead to site-selective peptide ...[more]

PMID: 31628819

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