Ferrocene bioconjugates with amino acids and carbohydrates

Kovačević, Monika (2014) Ferrocene bioconjugates with amino acids and carbohydrates. Doctoral thesis, Faculty of Science > Department of Chemistry.

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Abstract

In the first part of this dissertation the synthesis and conformational analysis of bioconjugates 21-32 [derived by condensation of ferrocene-1,1’-diamine (Fcda) with natural peptides Ala-Pro and Pro-Ala] and their precursors 1-14 are described. In order to explore the impact of chirality and sequence of amino acids, as well as effect of N-protecting groups on conformational space of prepared compounds, the detailed conformational analysis (IR, NMR and CD spectroscopy, DFT calculations) was performed. It was demonstrated that (i) peptides 21-32 [Y-(AA) n -NH-Fn-NH-(AA)-Y, Fn = ferrocenylene, AA = D(L)-Pro, D(L)-Ala, Y = Ac(acetyl), Boc (tert-butoxycarbonyl), m,n = 1, 2] form ß- and γ-turns through intermolecular m hydrogen bonding (IHB) and (ii) chirality and sequence of amino acids as well as protecting groups affect the IHB motifs. In the second part of this dissertation, dealing with bioconjugates of ferrocenes and carbohydrates, the synthesis of ferrocene muropeptides N-Ac-(iso)Mur-NH-Fn-R, (44-48, Mur = muramic acid, R = H, COOMe, NHAc) and conjugates N-Ac-Mur-L(D)-Ala-Fca-OMe (49-52), an analogues of muramyl dipeptide (MDP, N-Ac-Mur-Ala-isoGln), was desribed. The influence of an organometallic moiety on the conformational properties of the synthesized compounds was examined by spectroscopic analysis corroborated with DFT modeling. Furthermore, the synthesis and inhibitory potency of ester and amide conjugates of ferrocene and mannose (67-72) toward Escherichia coli were presented.

Item Type: Thesis (Doctoral thesis)
Keywords: DFT, ferrocene, intramolecular hydrogen bonds, conformational analysis, mannosides, muropeptides, peptides
Supervisor: Barišić, Lidija
Date: 2014
Number of Pages: 275
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: mag. bibl. Ana Šafran
Date Deposited: 15 Oct 2014 10:17
Last Modified: 15 Jun 2015 12:16
URI: http://digre.pmf.unizg.hr/id/eprint/3057

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