Peptide boronic acids by late-stage hydroboration on the solid phase [research data]

• Verfasst von: Werner, Marius [VerfasserIn]
• Verfasst von: Brinkhofer, Julian [VerfasserIn]
• Verfasst von: Hammermüller, Leon [VerfasserIn]
• Verfasst von: Heim, Thomas [VerfasserIn]
• Verfasst von: Pham, Truc Lam [VerfasserIn]
• Verfasst von: Huber, Jonas [VerfasserIn]
• Verfasst von: Klein, Christian D. [VerfasserIn]
• Verfasst von: Thomas, Franziska [VerfasserIn]
• Titel: Peptide boronic acids by late-stage hydroboration on the solid phase [research data]
• Verf.angabe: Marius Werner, Julian Brinkhofer, Leon Hammermüller, Thomas Heim, Truc Lam Pham, Jonas Huber, Christian Klein, Franziska Thomas
• Verlagsort: Heidelberg
• Verlag: Universität
• E-Jahr: 2025
• Jahr: 2025-01-17
• Umfang: 1 Online Ressource (5 Files)
• Fussnoten: Gefördert durch: Deutsche Forschungsgemeinschaft (DFG): 414261058; Deutsche Forschungsgemeinschaft (DFG) - Excellence Strategy: 2082/1 390761711 ; Gesehen am 20.01.2025
• DOI: doi:10.11588/data/G9NMGA
• Datenträger: Online-Ressource
• Dokumenttyp: Forschungsdaten
• Dokumenttyp: Datenbank
• Sprache: eng
• Bibliogr. Hinweis: Forschungsdaten zu: Werner, Marius, 1998 - : Peptide boronic acids by late-stage hydroboration on the solid phase
• Sonstige Nr.: Grant number: DFG 414261058
• Sonstige Nr.: Grant number: DFG 2082/1 390761711
• Sach-SW: Chemistry
• K10plus-PPN: 1915108225
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

Organoboron compounds have a wide range of applications in numerous research fields, and methods to incorporate them in biomolecules are much sought after. Here, on-resin chemical syntheses of aliphatic and vinylogous peptide boronic acids are presented by transition metal-catalyzed late-stage hydroboration of alkene and alkyne groups in peptides and peptoids, for example on allyl- and propargylglycine residues, using readily available chemicals. These methods yield peptide boronic acids with much shorter linkers than previously reported on-resin methods. Furthermore, the methods are regio- and stereoselective, compatible with all canonical amino acid residues and can be applied to short, long, and in part even “difficult” peptide sequences. In a feasibility study, the protected peptide vinylboronic acids are further derivatized by the Petasis reaction using salicylaldehyde derivatives. The ability of the obtained peptide boronic acids to reversibly bind to carbohydrates is demonstrated in a catch-release model experiment using a fluorescently labeled peptide boronic acid on cross-linked dextran beads. In summary, this highlights the potential of the target compounds for drug discovery, glycan-specific target recognition, controlled release, and diagnostics.