TY - JOUR
T1 - Synthesis of Novel Arginine Building Blocks with Increased Lipophilicity Compatible with Solid-Phase Peptide Synthesis
AU - Glavaš, Mladena
AU - Gitlin-Domagalska, Agata
AU - Ptaszyńska, Natalia
AU - Starego, Dominika
AU - Freza, Sylwia
AU - Dębowski, Dawid
AU - Helbik-Maciejewska, Aleksandra
AU - Łęgowska, Anna
AU - Gilon, Chaim
AU - Rolka, Krzysztof
N1 - Publisher Copyright:
© 2023 by the authors.
PY - 2023/12
Y1 - 2023/12
N2 - 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.
AB - 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.
KW - arginine building blocks
KW - increased lipophilicity
KW - prodrugs
KW - SPPS
KW - vasopressin
UR - http://www.scopus.com/inward/record.url?scp=85179348079&partnerID=8YFLogxK
U2 - 10.3390/molecules28237780
DO - 10.3390/molecules28237780
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AN - SCOPUS:85179348079
SN - 1420-3049
VL - 28
JO - Molecules
JF - Molecules
IS - 23
M1 - 7780
ER -