Naslov
Optimization of synthetic route to ferrocene esters of desmuramyl dipeptides

Autori
Car, Željka ; Petrović Peroković, Vesna ; Kovačević, Monika ; Ribić, Rosana ; Barišić, Lidija

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

Izvornik
27th Croatian Meeting of Chemists and Chemical Engineers and 5th Symposium Vladimir Prelog : Book of Abstracts / Marković, Dean ; Meštrović, Ernest ; Namjesnik, Danijel ; Tomašić, Vesna - Zagreb : Hrvatsko kemijsko društvo, 2021, 182-182

Skup
27. hrvatski skup kemičara i kemijskih inženjera (27HSKIKI)

Mjesto i datum
Veli Lošinj, Hrvatska, 05.10.2021. - 08.10.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
adjuvants ; muramyl dipeptide ; desmuramyl peptide ; ferrocene esters of DMP ; ferrocene alcohols

Sažetak
Muramyl dipeptide (N-acetylmuramyl-L-alanyl-D- isoglutamine, MDP) is the smallest structural unit of peptidoglycans showing immunostimulating activity. [1] MDP analogues without the hydrophilic N-acetylmuramyl moiety are called desmuramyl peptides (DMP) and are extensively studied by our group as potential new adjuvants. [1] This work is a continuation of our ongoing SAR study of amphiphilic mannosyl DMP analogues and their synthesis. In order to prepare such compounds lipophilic DMP precursors are needed (Fig. 1a). Lipophilic subunits used so far have been adamantyl, adamantyl triazolyl, dodecyl and were introduced through an amide bond at the side chain or on α-carbon atom of D-isoGln residue. In this work we are optimizing the synthesis of ferrocene esters of DMP. The lipophilic ferrocene part is introduced on the D-isoGln side chain via several ferrocene alcohols (Fig. 1b). [2] In order to obtain the ester bond modified Steglich procedure was envisioned. In the case of ferrocenemethanol this procedure was not successful due to low nucleophilicity of its hydroxyl group. Therefore, in this work, several other methods for the preparation of its ester were explored.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA