Induced Chirality in Canthaxanthin Aggregates Reveals Multiple Levels of Supramolecular Organization

Author:

Halat Monika1ORCID,Zając Grzegorz2ORCID,Andrushchenko Valery3ORCID,Bouř Petr3ORCID,Baranski Rafal1ORCID,Pajor Katarzyna45ORCID,Baranska Malgorzata24ORCID

Affiliation:

1. Department of Plant Biology and Biotechnology University of Agriculture in Krakow Al. Mickiewicza 21 31-120 Krakow Poland

2. Jagiellonian Centre for Experimental Therapeutics Jagiellonian University Bobrzynskiego 14 30-348 Krakow Poland

3. Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo náměstí 2 16610 Prague Czech Republic

4. Faculty of Chemistry Jagiellonian University Gronostajowa 2 30-387 Krakow Poland

5. Doctoral School of Exact and Natural Sciences Jagiellonian University S. Łojasiewicza 11 30-348 Krakow Poland

Abstract

AbstractCarotenoids tend to form supramolecular aggregates via non‐covalent interactions where the chirality of individual molecules is amplified to the macroscopic level. We show that this can also be achieved for non‐chiral carotenoid monomers interacting with polysaccharides. The chirality induction in canthaxanthin (CAX), caused by heparin (HP) and hyaluronic acid (HA), was monitored by chiroptical spectroscopy. Electronic circular dichroism (ECD) and Raman optical activity (ROA) spectra indicated the presence of multiple carotenoid formations, such as H‐ and J‐type aggregates. This is consistent with molecular dynamics (MD) and density functional theory (DFT) simulations of the supramolecular structures and their spectroscopic response.

Funder

Narodowe Centrum Nauki

Grantová Agentura České Republiky

Infrastruktura PL-Grid

Academic Computer Centre Cyfronet, AGH University of Science and Technology

Ministerstvo Školství, Mládeže a Tělovýchovy

Publisher

Wiley

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