Making rings from amino acids. Shining light on possible (chemo)evolution of proline (CROSBI ID 724065)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija
Podaci o odgovornosti
Zubčić, Gabrijel ; Portada, Tomislav ; Biruš, Ivan ; Šakić, Davor
engleski
Making rings from amino acids. Shining light on possible (chemo)evolution of proline
Proline is an unusual proteinogenic alfa amino acid, where the side chain is connected to the amino group, forming a pyrrolidine ring and secondary amine. Due to its unique internal bonding it has different structural properties compared to other amino acids in peptides and proteins, including different ratio of cis/trans isomerism in peptide bonds, conformational rigidity and losing hydrogen-donating characteristics. Biosynthesis of proline starts from L-glutamate, proceeds through gamma- semialdehyde, that cyclizes to pyrrolidine- ring that is then reduced to proline. Generation of proline in primordial soup is not well understood. While it is possible that generation through Schiff base mechanism is possible, here we provide an alternative. Pyrrolidine rings can be formed through Hofmann-Löffler-Freytag (HLF) reaction. This reaction starts from halogenated amine, which under illumination or heating cleaves homolytically, generating N-centred radical. Rearrangement of N- centred radical to C-centered radical, and subsequent ring formation can be one of the ways proline is formed from nor-leucine. This reaction can also be used for synthesis of pharmacologically active compounds, such as nicotine derivatives. Here presented are simulations of thermodynamic and kinetic profile, synthesis, kinetic studies, and characterisation of proline derivatives utilising HLF reaction. Results can be used to describe structural changes and degradation in proteins in oxidative stress and high UV radiation conditions.
radicals, rearrangement, Hofmann-Löffler-Freytag (HLF) reaction
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Podaci o prilogu
159-159.
2022.
objavljeno
Podaci o matičnoj publikaciji
Book of Abstracts of the Congress of the Croatian Society of Biochemistry and Molecular Biology HDBMB22: From Science to Knowledge
Dulić, Morana ; Sinčić, Nino ; Vrhovac Madunić, Ivana
Zagreb: Hrvatsko društvo za biokemiju i molekularnu biologiju (HDBMB)
1847-7836
Podaci o skupu
HDBMB22: From Science to Knowledge
predavanje
01.01.2022-01.01.2022
Brela, Hrvatska