TY - JOUR
T1 - Accelerated solid-phase synthesis of glycopeptides containing multiple N-glycosylated sites
AU - Strauss, Poriah
AU - Nuti, Francesca
AU - Quagliata, Michael
AU - Papini, Anna Maria
AU - Hurevich, Mattan
N1 - Funding Information: This work was partly supported by the Rita Levi Montalcini Prize for scientific cooperation between Italy (University of Florence) and Israel (Weizmann Institute of Science, Hebrew University, and Bar Ilan University) to A. M. P. (Israel Council for Higher Education grant 2018, attributed in 2019). P. S. thanks the Hebrew University Center for Nanoscience and Nanotechnology for the excellent M.Sc. student scholarship. Publisher Copyright: © 2023 The Royal Society of Chemistry.
PY - 2022/11/10
Y1 - 2022/11/10
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85142518840&partnerID=8YFLogxK
U2 - https://doi.org/10.1039/d2ob01886a
DO - https://doi.org/10.1039/d2ob01886a
M3 - Article
C2 - 36385318
SN - 1477-0520
VL - 21
SP - 1674
EP - 1679
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 8
ER -