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

Glavaš, Mladena; Gitlin-Domagalska, Agata; Ptaszyńska, Natalia; Starego, Dominika; Freza, Sylwia; Dębowski, Dawid; Helbik-Maciejewska, Aleksandra; Łęgowska, Anna; Gilon, Chaim; Rolka, Krzysztof (2023) Synthesis of Novel Arginine Building Blocks with Increased Lipophilicity Compatible with Solid-Phase Peptide Synthesis. Molecules, 28 (23). ISSN 1420-3049

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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.

Item Type:	Article
Uncontrolled Keywords:	arginine building blocks; increased lipophilicity; SPPS; vasopressin; prodrugs
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry NMR Center
Projects:	Project title Project leader Project code Project type National Science Center Poland Agata Gitlin-Domagalska UMO—2019/35/D/NZ7/00174 UNSPECIFIED
Depositing User:	Mladena Glavaš
Date Deposited:	17 Dec 2025 08:51
URI:	http://fulir.irb.hr/id/eprint/10537
DOI:	10.3390/molecules28237780

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