Issue 4, 2023

Chiral adaptive recognition with sequence specificity of aromatic dipeptides in aqueous solution by an achiral cage

Abstract

Sequence-specific recognition of peptides and proteins by synthetic compounds or systems remains a huge challenge in biocompatible media. Here, we report the chiral adaptive recognition (CAR) with sequence specificity of aromatic dipeptides in a purely aqueous solution using an achiral tetraphenylethene-based octacationic cage (1) as both a molecular receptor and chiroptical sensor. 1 can selectively bind and dimerize aromatic dipeptides to form 1 : 2 host–guest complexes with high binding affinity (>1010 M−2), especially up to ∼1014 M−2 for TrpTrp. Given the dynamic rotational conformation of TPE units, achiral 1 can exhibit chiral adaptive responses with mirror-symmetrical circular dichroism (CD) and circularly polarized luminescence (CPL) spectra to enantiomeric dipeptides via supramolecular chirality transfer in the host–guest complexes. Furthermore, this CAR with sequence specificity of 1 can be applied for molecular recognition of TrpTrp- or PhePhe-containing tetrapeptides, polypeptides (e.g., amyloid β-peptide1–20 and somatostatin), and proteins (e.g., human insulin) with characteristic CD responses.

Graphical abstract: Chiral adaptive recognition with sequence specificity of aromatic dipeptides in aqueous solution by an achiral cage

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Oct 2022
Accepted
15 Dec 2022
First published
17 Dec 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 833-842

Chiral adaptive recognition with sequence specificity of aromatic dipeptides in aqueous solution by an achiral cage

L. Cheng, P. Tian, H. Duan, Q. Li, X. Song, A. Li and L. Cao, Chem. Sci., 2023, 14, 833 DOI: 10.1039/D2SC05854E

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