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“Gear-Driven”-Type Chirality Transfer of Tetraphenylethene-Based Supramolecular Organic Frameworks for Peptides in Water
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  • Chaochao Yan,
  • Qingfang Li,
  • Kaige Wang,
  • Wanni Yang,
  • Jingyu Han,
  • Yawen Li,
  • Yunhong Dong,
  • Dake Chu,
  • Lin Cheng,
  • Liping Cao
Chaochao Yan
Northwest University
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Qingfang Li
Northwest University
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Kaige Wang
Northwest University
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Wanni Yang
Northwest University
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Jingyu Han
Northwest University
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Yawen Li
Northwest University
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Yunhong Dong
Northwest University
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Dake Chu
Xi’an Jiaotong University
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Lin Cheng
Northwest University
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Liping Cao
Northwest University

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Abstract

Chirality transfer for natural chiral biomolecules can reveal the indispensable role of chiral structures in life and can be used to develop the chirality-sensing biomolecular recognition. Here, we report the synthesis and characterization of a series of achiral supramolecular organic frameworks (SOF-1, SOF-2, and SOF-3), constructed from cucurbit[8]uril (CB[8]) and tetraphenylethene (TPE) derivatives (1, 2, and 3), respectively, as chirality-sensing platforms to explore their chirality transfer mechanism for peptides in water. Given the right-handed (P) and left-handed (M) rotational conformation of TPE units and the selective binding of CB[8] to aromatic amino acids, these achiral SOFs can be selectively triggered in water by peptides containing N-terminal tryptophan (W) and phenylalanine (F) residues into their P- or M-rotational conformation, exhibiting significantly different circular dichroism (CD) spectra. Although various peptides have the same L-type chiral configuration, they can induce positive CD signals of SOF-1 and negative CD signals of SOF-2 and SOF-3, respectively. Based on the structural analysis of the linkage units between CB[8] and TPE units in these SOFs, a “gear-driven”-type chirality transfer mechanism has been proposed to visually illustrate the multiple-step chirality transfer process from the recognition site in the CB[8]’s cavity to TPE units. Furthermore, by utilizing the characteristic CD signals generated through the “gear-driven”-type chirality transfer, a series of SOFs can serve as chiroptical sensor arrays to effectively recognize and distinguish various peptides based on their distinctive CD spectra.