Arginine building blocks with increased lipophilicity – synthesis and application

Glavaš, Mladena; Gitlin-Domagalska, Agata; Ptaszyńska,, Natalia; Starego, Dominika Arginine building blocks with increased lipophilicity – synthesis and application. In: Book of abstracts. p. 85 .

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Abstract

Peptides have the crucial role in all living organisms [1]. They act as hormones, antibodies, neurotransmitters and play a role in development of many diseases [2]. In addition, peptides are used as functional materials [3] and pharmaceuticals [4]. However, natural peptides possess some properties that are less desirable, the most interfering are [4,5] inability to cross intestinal epithelial barrier and limited stability toward proteolysis. To overcome this impediments and make peptides more familiar to body functions, specific modifications are introduced [1,6]. Vasopressin (AVP) is one of well described peptide hormone. It is a nonapeptide (Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2) which consist of tripeptide tail and a six residues cyclic structure by disulfide bridge [7]. The main function is antidiuretic [8], but AVP helps to increase the blood pressure in septic shock, maintain cardiovascular homeostasis [8a,8c], etc. The aim of our synthesis was preparation of modified arginine (Arg) and using in the solid phase peptide synthesis (SPPS) for the preparation of AVP analogues characterized by increased lipophilicity (Figure 1). The synthesis started with the preparation of guanidynylating reagents (A, Figure 1) from guanidine hydrochloride and chloroformates [9]. In the next step, unusual amino acid, namely ornithine, reacted with compound A to produced Arg derivatives with masked guanidine group (B, Figure 1). In the last step, analogues of AVP were obtained in moderate yield, applying SPPS

Item Type:	Conference or workshop item published in conference proceedings (UNSPECIFIED)
Uncontrolled Keywords:	peptides; vasopressin; AVP; modified arginine; solid phase peptide synthesis (SPPS)
Subjects:	NATURAL SCIENCES NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Chemistry > Organic Chemistry NATURAL SCIENCES > Biology NATURAL SCIENCES > Biology > Biochemistry and Molecular Biology
Divisions:	NMR Center
Projects:	Project title Project leader Project code Project type NSC projekt: Lipophilic Prodrug Charge Masking (LPCM) as a novel strategy to enhance oral bioavailability of charged active peptides. Optimization and generalization of the method Agata Gitlin-Domagalska UMO-2019/35/D/NZ7/00174 UNSPECIFIED
Depositing User:	Mladena Glavaš
Date Deposited:	18 Dec 2025 09:07
URI:	http://fulir.irb.hr/id/eprint/10586

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