Naslov
Synthesis, structural characterization and biological activities of desmuramyl peptide derivatives

Autori
Paurević, Marija ; Ribić, Rosana ; Kodrin, Ivan ; Tomić, Srđanka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, neobjavljeni rad, znanstveni

Skup
European School of Medicinal Chemistry - XXXVIII Advanced Course of Medicinal Chemistry and Seminar for PhD students

Mjesto i datum
Urbino, Italija, 01.07.2018. - 05.07.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Muramyldipeptide ; D-Mannose ; Immunostimulating activity ; Peptide synthesis
(muramyldipeptide ; D-mannose ; immunostimulating activity ; peptide synthesis)

Sažetak
Muropeptides, also called peptidoglycans, are fragments of unique polymers that build up the cell wall of bacteria. Muramyl dipeptide (MDP), N- acetylmuramyl-L-alanyl-D-isoglutamine, is the smallest structural unit of peptidoglycans showing the immunostimulating (adjuvant) activity. Dipeptide core of MDP is the essential structure required for adjuvant activity, therefore, MDP analogues lacking the hydrophilic carbohydrate moiety, desmuramyl peptides, are explored. Numerous derivatives with different groups at C- and N-terminus of the L-Ala-D- isoGln moiety are known. We have designed and synthesized desmuramyl peptides with incorporated lipophilic adamantyl group and also their mannosylated derivatives. Conformational study of desmuramyl dipeptide, its tripeptide analogue with incorporated bulky lipophylic adamantyl substituent at the N- terminal amino acid and serine derivative of adamantyl tripeptide was also performed. Attached mannose allows the targeting of cell surface receptors recognizing glycans on immune cells while adamantane group facilitates the anchoring of the peptidoglycan ‘cargo’ to the membrane. In order to improve lectin-carbohydrate binding, we are also developing methodology for the stereoselective synthesis of dimannosylated desmuramylpeptides because we believe that increasing of mannose subunits number will enhance strength of overall mannose – lectin interactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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