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1'-Acetylferrocene Amino Acid Esters and Amides. A simple model for parallel beta-helical peptides


Djaković, Senka; Kodrin, Ivan; Smrečki, Vilko; Novak, Predrag; Mihalić, Zlatko; Žiher, Dinko; Lapić, Jasmina; Rapić, Vladimir
1'-Acetylferrocene Amino Acid Esters and Amides. A simple model for parallel beta-helical peptides // Tetrahedron, 70 (2014), 14; 2330-2342 doi:10.1016/j.tet.2014.02.047 (međunarodna recenzija, članak, znanstveni)


Naslov
1'-Acetylferrocene Amino Acid Esters and Amides. A simple model for parallel beta-helical peptides

Autori
Djaković, Senka ; Kodrin, Ivan ; Smrečki, Vilko ; Novak, Predrag ; Mihalić, Zlatko ; Žiher, Dinko ; Lapić, Jasmina ; Rapić, Vladimir

Izvornik
Tetrahedron (0040-4020) 70 (2014), 14; 2330-2342

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Ferrocene; bioconjugates; conformational analysis; hydrogen bonds; density functional theory (DFT)

Sažetak
In this study we present a synthesis and conformational analysis of 1’-acetylferrocene amino acid derivatives of type Ac-Fn-CO-AA-Y (Fn = ferrocene-1, 1-diyl ; AA = Gly, Ala or Val ; Y = OMe or NHMe) as a model for parallel beta-helical peptides. Derivatives with only one amino acid instead of a dipeptide adopt a reduced number of total conformations and allow a more exact analysis of intramolecular hydrogen bonds (IHB) close to the ferrocene unit. Conformational analysis of these bioconjugates was performed by a combination of spectroscopic techniques (IR, NMR and CD) and corroborated by solution-phase DFT calculations. The investigation of ester conjugates 1-3 indicates the coexistence of non- bonded (in open forms) and hydrogen bonded NHa group forming a 7-membered ring (γ-turn). The amide derivatives 4-6 with an additional NHb hydrogen bond donor are mostly constituted of conformers with a 10-membered ring (-turn). This is usually accompanied by a 7-membered ring (γ- ring) containing NHa group or by a single IHB pattern. Additionally, the exchange of the amino acid side-chain does not significantly affect the conformational properties and IHB patterns of the studied conjugates 1-6.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
058-1191344-3122 - Metalocenski biokonjugati, heterocikli i makromolekule (Veronika Kovač, )
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, )
119-1191342-1083 - Interakcije i dizajn bioaktivnih molekula (Predrag Novak, )
119-1191342-1339 - Molekulsko modeliranje strukture i reaktivnosti organskih spojeva (Zlatko Mihalić, )

Ustanove
Prehrambeno-biotehnološki fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


Uključenost u ostale bibliografske baze podataka:


  • CAB Abstracts


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