Chiral Amplification in Nature: Studying Cell‐Extracted Chiral Carotenoid Microcrystals via the Resonance Raman Optical Activity of Model Systems

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-06, Vol.58 (25), p.8383-8388
Main Authors: Dudek, Monika, Machalska, Ewa, Oleszkiewicz, Tomasz, Grzebelus, Ewa, Baranski, Rafal, Szcześniak, Piotr, Mlynarski, Jacek, Zajac, Grzegorz, Kaczor, Agnieszka, Baranska, Malgorzata
Format: Article
Language:English
Subjects:
Aggregates
Amplification
Astaxanthin
Carotene
carotenoid microcrystals
Carotenoids
Chirality
chirality induction
Crystallization
Information transfer
Lutein
Microcrystals
Military
Optical activity
resonance Raman Optical Activity
Seeds
sergeant-and-soldiers effect
supramolecular chirality
β-Carotene
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Summary: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′‐[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. Chirality induction: Natural microcrystals and model aggregates consist mainly of achiral β‐carotene together with a small amount of chiral carotenoids. According to the sergeant‐and‐soldiers effect, a chiral signal is thus amplified, which can be observed by means of electronic circular dichroism (ECD) and resonance Raman optical activity (RROA) studies.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201901441