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

Abstract

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.
Author Monika Dudek
Monika Dudek,,
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, Ewa Machalska
Ewa Machalska,,
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, Tomasz Oleszkiewicz (FoBaH / IoPBaB)
Tomasz Oleszkiewicz,,
- Institute of Plant Biology and Biotechnology
, Ewa Grzebelus (FoBaH / IoPBaB)
Ewa Grzebelus,,
- Institute of Plant Biology and Biotechnology
, Rafał Barański (FoBaH / IoPBaB / DoGPBaSP)
Rafał Barański,,
- Department of Genetics, Plant Breeding and Seed Production
, Piotr Szcześniak
Piotr Szcześniak,,
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, Jacek Młynarski
Jacek Młynarski,,
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, Grzegorz Zając
Grzegorz Zając,,
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, Agnieszka Kaczor
Agnieszka Kaczor,,
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, Małgorzata Barańska
Małgorzata Barańska,,
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Journal seriesAngewandte Chemie-International Edition, [Angewandte Chemie - International Edition], ISSN 1433-7851, e-ISSN 1521-3773, (N/A 200 pkt)
Issue year2019
Vol58
No25
Pages8383-8388
Publication size in sheets0.5
Keywords in Englishcarotenoid microcrystals, chirality induction, resonance Raman Optical Activity, sergeant-and-soldiers effect, supramolecular chilarity
ASJC Classification1503 Catalysis; 1600 General Chemistry
DOIDOI:10.1002/anie.201901441
URL https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.201901441
Languageen angielski
Score (nominal)200
Score sourcejournalList
Publication indicators WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 2.132; WoS Impact Factor: 2018 = 12.257 (2) - 2018=12.359 (5)
Citation count*2 (2020-03-10)
Additional fields
FinansowanieThis work was supported by the National Science Centre (2017/25/B/ST4/00854 and 2018/29/N/ST4/00690)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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