Synthesis of Novel Arginine Building Blocks with Increased Lipophilicity Compatible with Solid-Phase Peptide Synthesis

Mladena Glavaš, Agata Gitlin-Domagalska*, Natalia Ptaszyńska, Dominika Starego, Sylwia Freza, Dawid Dębowski, Aleksandra Helbik-Maciejewska, Anna Łęgowska, Chaim Gilon, Krzysztof Rolka

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Arginine, due to the guanidine moiety, increases peptides’ hydrophilicity and enables interactions with charged molecules, but at the same time, its presence in a peptide chain might reduce its permeability through biological membranes. This might be resolved by temporary coverage of the peptide charge by lipophilic, enzyme-sensitive alkoxycarbonyl groups. Unfortunately, such a modification of a guanidine moiety has not been reported to date and turned out to be challenging. Here, we present a new, optimized strategy to obtain arginine building blocks with increased lipophilicity that were successfully utilized in the solid-phase peptide synthesis of novel arginine vasopressin prodrugs.

Original languageEnglish
Article number7780
JournalMolecules
Volume28
Issue number23
DOIs
StatePublished - Dec 2023

Bibliographical note

Publisher Copyright:
© 2023 by the authors.

Keywords

  • arginine building blocks
  • increased lipophilicity
  • prodrugs
  • SPPS
  • vasopressin

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