Issue 49, 2021
From the journal:

Chemical Communications

Cucurbit[8]uril facilitated Michael addition for regioselective cysteine modification†

Gao Li, ORCID logo *a   Jun Hu,b   Huai Chen,b   Yong-Xiang Chen ORCID logo b  and  Yan-Mei Li ORCID logo *bcd  

* Corresponding authors

a Institute of Oceanography, Minjiang University, Fuzhou, Fujian 350108, China
E-mail: ligao2019@mju.edu.cn

b Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China
E-mail: liym@mail.tsinghua.edu.cn

c Beijing Institute for Brain Disorders, Beijing 100069, China

d Center for Synthetic and Systems Biology, Tsinghua University, Beijing 100084, China

Abstract

Utilizing the interactions between tryptophan, methyl viologen and cucurbit[8]uril, we found that the distance between the targeted peptides/protein and the reactive peptide was shortened, which facilitated the Michael addition reaction between cysteine and dehydroalanine. The highest acceleration was observed on cysteines with suitable pKa and spatial location to tryptophan, suggesting that our system can be used for regioselective cysteine modification.

Graphical abstract: Cucurbit[8]uril facilitated Michael addition for regioselective cysteine modification

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Article information

DOI
https://doi.org/10.1039/D1CC01404H
Article type
Communication
Submitted
15 Mar 2021
Accepted
19 May 2021
First published
19 May 2021

Chem. Commun., 2021,57, 6086-6089

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Cucurbit[8]uril facilitated Michael addition for regioselective cysteine modification

G. Li, J. Hu, H. Chen, Y. Chen and Y. Li, Chem. Commun., 2021, 57, 6086 DOI: 10.1039/D1CC01404H

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