Naslov
The effects of the backbone chirality, amino acid sequence and the N-terminal group on the conformational properties of ferrocene peptidomimetics

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

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

Izvornik
3rd International Congress of Chemists and Chemical Engineers of Bosnia and Herzegovina : Book of abstracts, Special Issue of Bulletin of the Chemists and Technologists of Bosnia and Herzegovina / Korać, Fehim - Sarajevo, 2018, 117-117

Skup
3rd International Congress of Chemists and Chemical Engineers of Bosnia and Herzegovina

Mjesto i datum
Sarajevo, Bosna i Hercegovina, 19.10.2018. - 21.10.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Recenziran

Ključne riječi
Ferrocene ; Peptidomimetic ; Conformational analysis

Sažetak
Our previous work on peptides that contain homo- and heterochiral Ala‒Pro sequences attached to the turn-inducing ferrocene-1, 1’-diamine scaffold have revealed different conformational properties of homo- and heterochiral peptides. An exchange of two N-terminal groups had a somewhat larger influence on the distribution of the hydrogen-bond patterns in homochiral than in heterochiral derivatives. In order to get more detailed insight into conformational patterns of ferrocene-containing peptides, we have coupled 1'-aminoferrocene-1-carboxylate with homo- and heterochiral peptides Ala‒Pro and Pro‒Ala. The influence of amino acid sequence, backbone chirality and different bulkiness and basicity of the N-terminal Boc and Ac groups on the conformational behaviour of the corresponding peptides was systematically explored by IR, NMR, and CD spectroscopy. Although the observed intramolecular hydrogen-bond patterns permitted all NH groups belonging to ferrocene unit (NHFn) to be involved in turn-stabilizing interactions, the NHFn groups of heterochiral peptides were found to be involved in a stronger hydrogen bonds. The strength of hydrogen-bonding interactions was also influenced by amino acid sequence and N-terminal group.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA