Chiral Amplification in Nature: Studying Cell‐Extracted Chiral Carotenoid Microcrystals via the Resonance Raman Optical Activity of Model Systems
Monika Dudek , Ewa Machalska , Tomasz Oleszkiewicz , Ewa Grzebelus , Rafał Barański , Piotr Szcześniak , Jacek Młynarski , Grzegorz Zając , Agnieszka Kaczor , Małgorzata Barańska
AbstractCarotenoid microcrystals, extracted from cells of carrot roots and consisting of 95 % of achiral β‐carotene, exhibit a very intense chiroptical (ECD and ROA) signal. The preferential chirality of crystalline aggregates that consist mostly of achiral building blocks is a newly observed phenomenon in nature, and may be related to asymmetric information transfer from the chiral seeds (small amount of α‐carotene or lutein) present in carrot cells. To confirm this hypothesis, we synthesized several model aggregates from various achiral and chiral carotenoids. Because of the sergeant‐and‐soldier behavior, a small number of chiral sergeants (α‐carotene or astaxanthin) force the achiral soldier molecules (β‐ or 11,11′‐[D2]‐β‐carotene) to jointly form supramolecular assemblies of induced chirality. The chiral amplification observed in these model systems confirmed that chiral microcrystals appearing in nature might consist predominantly of achiral building blocks and their supramolecular chirality might result from the co‐crystallization of chiral and achiral analogues.
|Journal series||Angewandte Chemie-International Edition, [Angewandte Chemie - International Edition], ISSN 1433-7851, e-ISSN 1521-3773, (N/A 200 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||carotenoid microcrystals, chirality induction, resonance Raman Optical Activity, sergeant-and-soldiers effect, supramolecular chilarity|
|Publication indicators||= 0; : 2018 = 2.132; : 2018 = 12.257 (2) - 2018=12.359 (5)|
|Citation count*||2 (2020-03-10)|
|Finansowanie||This work was supported by the National Science Centre (2017/25/B/ST4/00854 and 2018/29/N/ST4/00690)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.