Metal-ion-assisted synthesis of cyclic homopeptides (CROSBI ID 648930)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa
Podaci o odgovornosti
Vidović, Nikolina ; Riva, Davide ; Horvat, Gordan ; Cindro, Nikola ; Meštrović, Jerko ; Tomišić, Vladislav ; Speranza, Giovanna
engleski
Metal-ion-assisted synthesis of cyclic homopeptides
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.
ion binding ; cyclic peptides ; metal-ion-assisted synthesis ;
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Podaci o prilogu
152-152.
2017.
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objavljeno
978-953-55232-7-7
Podaci o matičnoj publikaciji
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
Podaci o skupu
25. HRVATSKI SKUP KEMIČARA I KEMIJSKIH INŽENJERA s međunarodnim sudjelovanjem, 3.simpozij „VLADIMIR PRELOG“
poster
19.04.2017-22.04.2017
Zagreb, Hrvatska; Poreč, Hrvatska