Role of Achiral Nucleobases in Multicomponent Chiral Self-Assembly: Purine-Triggered Helix and Chirality Transfer.
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.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid Interface and Chemical Thermodynamics Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P.R. China.|University of Chinese Academy of Sciences, Beijing, 1, 00049, P.R. China.
Ming
M
Deng
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid Interface and Chemical Thermodynamics Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P.R. China.
Li
L
Zhang
Laboratory for Nanosystem and Hierarchy Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, 100190, P.R. China.
Yuqian
Y
Jiang
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid Interface and Chemical Thermodynamics Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P.R. China.|University of Chinese Academy of Sciences, Beijing, 1, 00049, P.R. China.|Laboratory for Nanosystem and Hierarchy Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, 100190, P.R. China.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P.R. China.
Minghua
M
Liu
D005449:Fluorenes / Q000737:chemistry*; D005453:Fluorescence; D018698:Glutamic Acid / Q000737:chemistry*; D049329:Nanostructures / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*
C496789:9-fluorenylmethoxycarbonyl; D005449:Fluorenes; D011687:Purines; D018698:Glutamic Acid; C030985:purine
chirality transfer; circular polarized fluorescence; helical structures; nucleobases; purines