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Synthesis of multiantenNary mannose derived DESMURAMYL PEPTIDES


Ribić, Rosana; Paurević, Marija; Tir, Nora; Tomić, Srđanka
synthesis of multiantenNary mannose derived DESMURAMYL PEPTIDES // Book of Abstract, 10th Joint Meeting on Medicinal Chemistry, June 25-28, 2017, Dubrovnik, Croatia / Basarić, Nikola ; Namjesnik, Danijel ; Perković, Ivana ; Stepanić, Višnja (ur.).
Zagreb, 2017. str. 208-208 (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Synthesis of multiantenNary mannose derived DESMURAMYL PEPTIDES

Autori
Ribić, Rosana ; Paurević, Marija ; Tir, Nora ; Tomić, Srđanka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of Abstract, 10th Joint Meeting on Medicinal Chemistry, June 25-28, 2017, Dubrovnik, Croatia / Basarić, Nikola ; Namjesnik, Danijel ; Perković, Ivana ; Stepanić, Višnja - Zagreb, 2017, 208-208

ISBN
978-953-55232-8-4

Skup
10th Joint Meeting on Medicinal Chemistry

Mjesto i datum
Dubrovnik, Hrvatska, 25.-28.06.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
DESMURAMYL PEPTIDES ; ADAMANTYL ; MANNOSYL

Sažetak
Muropeptides are fragments of peptidoglycans, unique polymers that build up the cell wall of bacteria. They are used as immunostimulating compounds (adjuvants). Muramyl dipeptide (MDP), N-acetylmuramyl-L-alanyl-D-isoglutamine, is the smallest structural unit of peptidoglycans showing the immunostimulating activity. Numerous MDP analogues lacking the hydrophilic carbohydrate moiety (desmuramyl peptides) with different groups at C- and N-terminus of the L- Ala-D-isoGln moiety have been synthesized. [1] We have designed and synthesized desmuramyl peptides with incorporated lipophilic adamantyl group and also their mannosylated derivatives. [2, 3] 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. Synthesized desmuramyl peptides have been encapsulated into liposomes, vehicles often used for the target delivery. In these liposomal formulations adamantane group penetrates into the lipid bilayer while mannose is exposed at the liposome surface and can serve in targeting mannose receptors. [4] In order to improve lectin-carbohydrate binding we are developing methodology for the stereoselective synthesis of di- and tri- antennary mannose derivatives of desmuramyl peptides because increasing of mannose subunits number will enhance strength of overall mannose – lectin interactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove
Prirodoslovno-matematički fakultet, Zagreb,
Sveučilište J. J. Strossmayera u Osijeku