Naslov
Metal-ion-assisted synthesis of cyclic homopeptides

Autori
Vidović, Nikolina ; Riva, Davide ; Horvat, Gordan ; Cindro, Nikola ; Meštrović, Jerko ; Tomišić, Vladislav ; Speranza, Giovanna

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

Izvornik
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog : knjiga sažetaka / Đaković, Marijana ; Miljanić, Snežana ; Šantić, Ana ; Vianello, Robert - Zagreb : Hrvatsko kemijsko društvo, 2017, 152-152

ISBN
978-953-55232-7-7

Skup
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. Simpozij Vladimir Prelog

Mjesto i datum
Poreč, Hrvatska, 19.04.2017. - 22.04.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
ion binding ; cyclic peptides ; metal-ion-assisted synthesis ;

Sažetak
In the recent years cyclic peptides have attracted attention since they find applications in many fields from drug discovery to nanomaterials. These compounds are difficult to prepare due to the fact that the activated peptide must adopt an entropically disfavoured conformation before forming the desired product [1]. The most important factor for successful peptide macrocyclization is ring size. Peptides that contain less than seven aminoacids are troublesome to cyclize [2]. In this work we describe the synthesis of small cyclic homopeptides containig 4-6 aminoacids. Cyclic peptides are also known as versatile ion-binders [3] but their binding affinities are often reduced by the inadequate orientation of amide functional groups. To overcome these problems, cyclopeptides will be conjugated to a molecules with rigid geometry [4], such as calixarenes. Cyclic homolysine and cyclic homoserine will be bind to calixarenes exploiting functional groups on peptide's side chain, . Influence of the lenght of side chains on affinities of this conjugates towards different anions will be investigated. Linear precursors were sinthesized using standard solution phase peptide synthesis and HOBt, HBTU as a coupling reagents. A three-dimensional orthogonal protection scheme was required to build the linear peptides, to deprotect the N- and C- termini and to cyclize them in a head- to-tail fashion. To promote the cyclization, different alkali metal ions were used depending on the size of the desired cyclic peptide. These ions coordinate amidic oxygen atoms along the chain forcing the linear peptide to form a strong turn structure and to bring the N- and C-termini closer, allowing in that way cyclization to occur.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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