engleski

Synthesis and Conformational Analysis of Methyl N-alanyl-1’-aminoferrocene-1-carboxylate

Structurally different ferrocene peptides I–VI exhibit considerable conformational differences. This study has explored the structural properties of VII [Y-AA-Fca-OMe ; Y = di-tert-butyl dicarbonate (Boc), acetyl (Ac) ; AA = L-Ala, DAla ; Fca = 1-aminoferrocene-1-carboxylic acid] with an exchanged sequence of constituent amino acids relative to VI (Y-Fca-AA-OMe ; Y = Boc, Ac ; AA = L-Ala, D-Ala). The ferrocene peptides VII were obtained by coupling C-protected Fca with Boc-L-Ala-OH and Boc-D-Ala-OH, respectively. The Boc protecting groups of the obtained conjugates Boc-AAFca-OMe (2a, AA = L-Ala ; 2b, AA = D-Ala) were convertedto sterically less demanding Ac groups to give Ac-AA-Fca-OMe (3a, AA = L-Ala ; 3b, AA = D-Ala). In order to examine their conformational properties, peptides VII were subjectedto spectroscopic analysis (IR, 1H NMR, CD) and molecular modeling (DFT). The alteration of peptides VI into VII significantly influenced their conformational properties. Conjugates VI were stabilized through interchain hydrogen bonding, whereas inter- and intrachain hydrogen bonds were established in their constitutional isomers VII. The replacement of the bulky Boc group with an Ac group did not cause major conformational changes, and the absolute configuration of the alanine chiral centers did not affect the conformational properties.

conformation analysis; density functional calculations; peptides; hydrogen bonds; spectroscopic analysis

Rad je kao poster prezentiran na skupu XXIII. hrvatski skup kemičara i kemijskih inženjera, održanom od 21.-24.04.2013.g., Osijek, Hrvatska ; uz domacu recenziju objavljen u Knjizi sažetaka / Andrea Hadžiev, Zdenko Blažeković (ur.) ; Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa, 2013 ; str. 169-169 ; ISBN 9789536894505.