Peptide fragments of glycoproteins containing multiple N-glycosylated sites are essential biochemical tools not only to investigate protein-protein interactions but also to develop glycopeptide-based diagnostics and immunotherapy. However, solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites is hampered by difficult couplings, which results in a substantial drop in yield. To increase the final yield, large amounts of reagents but also time-consuming steps are required. Therefore, we propose herein to utilize heating and stirring in combination with low-loading solid supports to set up an accelerated route to obtain, by an efficient High-Temperature Fast Stirring Peptide Synthesis (HTFS-PS), glycopeptides containing multiple N-glycosylated sites using equimolar excess of the precious glycosylated building blocks.

Accelerated solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites / Strauss, Poriah; Nuti, Francesca; Quagliata, Michael; Papini, Anna Maria; Hurevich, Mattan. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - ELETTRONICO. - (2022), pp. 1-6. [10.1039/D2OB01886A]

Accelerated solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites

Nuti, Francesca;Quagliata, Michael;Papini, Anna Maria
;
2022

Abstract

Peptide fragments of glycoproteins containing multiple N-glycosylated sites are essential biochemical tools not only to investigate protein-protein interactions but also to develop glycopeptide-based diagnostics and immunotherapy. However, solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites is hampered by difficult couplings, which results in a substantial drop in yield. To increase the final yield, large amounts of reagents but also time-consuming steps are required. Therefore, we propose herein to utilize heating and stirring in combination with low-loading solid supports to set up an accelerated route to obtain, by an efficient High-Temperature Fast Stirring Peptide Synthesis (HTFS-PS), glycopeptides containing multiple N-glycosylated sites using equimolar excess of the precious glycosylated building blocks.
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Strauss, Poriah; Nuti, Francesca; Quagliata, Michael; Papini, Anna Maria; Hurevich, Mattan
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/1289444
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