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 Okt 2022
Accepted
15 Dez 2022
First published
17 Dez 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements