Naslov
Syynthesis and conformational analysis of peptidomimetics composed of ferrocene-1, 1'- diamine and natural amino acids

Autori
Kovačević, Monika ; Kodrin, Ivan ; Roca, Sunčica ; Barišić, Lidija

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

Izvornik
25. hrvatski skup kemičara i kemijskih inženjera / Đaković, Marijana ; Šantić, Ana - Zagreb : Hrvatsko kemijsko društvo, 2017, 136-136

ISBN
978-953-55232-7-7

Skup
25. hrvatski skup kemičara i kemijskih inženjera

Mjesto i datum
Poreč, Hrvatska, 19.04.2017. - 22.04.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Ferrocene ; Peptidomimetic ; Conformational Analysis

Sažetak
1, n-Disubstituted ferrocenes were established as molecular templates for the design of turns and β- sheet-like structures as the almost free rotating cyclopentadiene rings are separated by about 3.3 Å which is ideal for interstrand hydrogen bonding in their conjugates with natural amino acids or peptides. It was clearly demonstrated that hydrogen bond donating/accepting properties of turn-inducing ferrocene scaffolds regulate the hydrogen bonding patterning of the derived peptides: the 10-membered interstrand hydrogen- bonded rings were established in the conjugates of the amino acids or peptides with dicarbonyl- functionalized ferrocene core, the 12-membered rings were formed in their conjugates with -NH-Fn- CO- moiety, while conjugation with diamino- functionalized ferrocene lead to the 14-membered hydrogen-bonded rings (also labelled as two simultaneous 10-membered β-turns) in the corresponding symmetrically disubstituted conjugates. Herein, we report the synthesis of orthogonally protected and desymmetrized peptides 1 and 2 composed of turn-nucleating ferrocene-1, 1’-diamine unit and homo- or heterochiral amino acid sequences. The effects of the backbone chirality and N-terminal protecting group on the conformational properties of the novel peptidomimetics are explored by IR, NMR and CD spectroscopy. The spectroscopic studies were augmented with DFT calculations.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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