Izvorni znanstveni članak

https://doi.org/10.5562/cca3557

Conformational Analysis of Cinhonine and Cinhonidine by Tensor Decomposition of Molecular Dynamics Trajectories

Karlo Sović ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Tea Ostojić ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Sara Cepić ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Alma Ramić ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Renata Odžak ; Department of Chemistry, Faculty of Science, University of Split, R. Boškovića 33, HR-21000 Split, Croatia
Mirjana Skočibušić ; Department of Biology, Faculty of Science, University of Split, R. Boškovića 33, HR-21000 Split, Croatia
Tomica Hrenar ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Ines Primožič ; Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia

Sažetak

Full conformational space of cinchonine and cinchonidine has been investigated by means of statistical analysis of quantum chemical molecular dynamics simulations. Recently developed procedure comprising principal component analysis of molecular dynamics trajectories was applied on cinchonine and cinchonidine as well as on their protonated and methylated quaternary derivatives. The method for full conformational analysis includes Cartesian coordinates sampling through quantum chemical molecular dynamics simulations, reduction of dimensionality by principal component analysis, determination of probability distributions in a reduced space of Cartesian coordinates and search for all the strict extrema points in probability distribution functions. In order to gain crucial insight in the understanding of chirality induction of these alkaloids, comparison of the determined conformational spaces of pseudo-enantiomers has been made. It was shown that protonation of the quinuclidine nitrogen atom stabilizes the conformers with the intramolecular 1N–H∙∙∙9O hydrogen bond whereas methylation on the same position results in the reduction of the domain of internal coordinates responsible for the conformational space.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi

cinchonine; cinchonidine; full conformational analysis; quantum chemical molecular dynamics; principal component analysis

Hrčak ID:

226756

URI

https://hrcak.srce.hr/226756

Datum izdavanja:

29.7.2019.

Posjeta: 2.017 *