Synthesis and conformational analysis of the conjugate of ferrocene‐1, 1'‐diamine and valine (CROSBI ID 676890)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa
Podaci o odgovornosti
Kovačević, Monika ; Dorić, Iva ; Čakić Semenčić, Mojca ; Kodrin, Ivan ; Milašinović, Valentina ; Barišić, Lidija
engleski
Synthesis and conformational analysis of the conjugate of ferrocene‐1, 1'‐diamine and valine
The ability of organometallic conjugates derived from 1, n‐disubstituted ferrocenes and Ala to adopt the turn or ‐sheet‐like structures was extensively studied [1‐5]. It was shown that hydrogen‐bond donor/acceptor 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 [1, 2], the 12‐membered interstrand rings were formed in their conjugates with ‒NH‒Fn‒ CO‒ moiety, [3] while conjugation with diaminofunctionalized ferrocene lead to the 14‐ membered interstrand hydrogen‐bonded rings which were also labelled as two simultaneous ten‐ membered rings [4, 5]. Herein, we report the synthesis of the conjugate I composed of ferrocene‐1, 1'‐diamine and valine. The influence of the turn‐inducing ferrocene scaffold and the bulkiness of valine side chains on the conformational properties of the derived bioconjugate is explored by IR, NMR and CD spectroscopy, DFT study and crystallographic analysis. The spectroscopic data of the novel compound in solution, that suggest a presence of one 10‐membered hydrogenbonded ring also known as β‐turn, are corroborated with DTF calculations.
ferrocene, peptidomimetic, conformational analysis
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Podaci o prilogu
133-133.
2019.
objavljeno
Podaci o matičnoj publikaciji
Galić, Nives ; Rogošić, Marko
Zagreb: Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI)
978-953-6894-67-3
Podaci o skupu
26. hrvatski skup kemičara i kemijskih inženjera (26HSKIKI) ; 4. simpozij Vladimir Prelog
poster
09.04.2019-12.04.2019
Šibenik, Hrvatska