Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 25, Pages 8383-8388Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901441
Keywords
carotenoid microcrystals; chirality induction; resonance Raman Optical Activity; sergeant-and-soldiers effect; supramolecular chirality
Categories
Funding
- National Science Centre [2017/25/B/ST4/00854, 2018/29/N/ST4/00690]
Ask authors/readers for more resources
Carotenoid microcrystals, extracted from cells of carrot roots and consisting of 95% of achiral beta-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 alpha-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 (alpha-carotene or astaxanthin) force the achiral soldier molecules (beta- or 11,11 '-[D-2]-beta-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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available