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Role of Achiral Nucleobases in Multicomponent Chiral Self‐Assembly: Purine‐Triggered Helix and Chirality Transfer
Author(s) -
Deng Ming,
Zhang Li,
Jiang Yuqian,
Liu Minghua
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608638
Subject(s) - nucleobase , chirality (physics) , self assembly , chemistry , helix (gastropod) , purine , stereochemistry , crystallography , dna , organic chemistry , biochemistry , enzyme , biology , physics , ecology , chiral symmetry breaking , quantum mechanics , snail , nambu–jona lasinio model , quark
Chiral self‐assembly is a basic process in biological systems, where many chiral biomolecules such as amino acids and sugars play important roles. Achiral nucleobases usually covalently bond to saccharides and play a significant role in the formation of the double helix structure. However, it remains unclear how the achiral nucleobases can function in chiral self‐assembly without the sugar modification. Herein, we have clarified that purine nucleobases could trigger N ‐(9‐fluorenylmethox‐ycarbonyl) (Fmoc)‐protected glutamic acid to self‐assemble into helical nanostructures. Moreover, the helical nanostructure could serve as a matrix and transfer the chirality to an achiral fluorescence probe, thioflavin T (ThT). Upon chirality transfer, the ThT showed not only supramolecular chirality but also circular polarized fluorescence (CPL). Without the nucleobase, the self‐assembly processes cannot happen, thus providing an example where achiral molecules played an essential role in the expression and transfer of the chirality.