Premium
Chiral Amplification in Nature: Studying Cell‐Extracted Chiral Carotenoid Microcrystals via the Resonance Raman Optical Activity of Model Systems
Author(s) -
Dudek Monika,
Machalska Ewa,
Oleszkiewicz Tomasz,
Grzebelus Ewa,
Baranski Rafal,
Szcześniak Piotr,
Mlynarski Jacek,
Zajac Grzegorz,
Kaczor Agnieszka,
Baranska Malgorzata
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901441
Subject(s) - chirality (physics) , supramolecular chirality , supramolecular chemistry , raman optical activity , astaxanthin , chemistry , carotenoid , molecule , ionone , racemic mixture , crystallization , crystallography , enantiomer , stereochemistry , organic chemistry , chiral symmetry breaking , physics , biochemistry , quantum mechanics , nambu–jona lasinio model , quark
Carotenoid 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′‐[D 2 ]‐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.