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- Title
Synthesis of Novel Arginine Building Blocks with Increased Lipophilicity Compatible with Solid-Phase Peptide Synthesis.
- Authors
Glavaš, Mladena; Gitlin-Domagalska, Agata; Ptaszyńska, Natalia; Starego, Dominika; Freza, Sylwia; Dębowski, Dawid; Helbik-Maciejewska, Aleksandra; Łęgowska, Anna; Gilon, Chaim; Rolka, Krzysztof
- 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.
- Subjects
PEPTIDE synthesis; SOLID-phase synthesis; LIPOPHILICITY; ARGININE; BIOLOGICAL membranes; PEPTIDES; POLYETHERSULFONE; COPEPTINS
- Publication
Molecules, 2023, Vol 28, Issue 23, p7780
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28237780