A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides |
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| Authors: | Dr Markus Julian Schöwe Dr Odin Keiper Prof Dr Carlo Unverzagt Prof Dr Valentin Wittmann |
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| Institution: | 1. Department of Chemistry, University of Konstanz, 78457 Konstanz, Germany;2. Bioorganic Chemistry, University of Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany |
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| 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. |
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| Keywords: | bioorganic chemistry glycopeptides ligation solid-phase peptide synthesis thioacids |
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