Issue 11, 2023
From the journal:

Chemical Communications

A unique reaction of diphenylcyclopropenone and 1,2-aminothiol with the release of thiol for multiple bioconjugation†

Shanshan Liu,‡a   Haishun Ye,‡a   Long Yi ORCID logo *a  and  Zhen Xib  

* Corresponding authors

a State Key Laboratory of Organic–Inorganic Composites and Beijing Key Lab of Bioprocess, Beijing University of Chemical Technology (BUCT), Beijing 100029, China
E-mail: yilong@mail.buct.edu.cn

b State Key Laboratory of Elemento-Organic Chemistry and Department of Chemical Biology, College of Chemistry, National Pesticide Engineering Research Center, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China

Abstract

Selective reaction of diphenylcyclopropenone (DPCP) and 1,2-aminothiol in water at pH 7.4 produces an amide conjugate with the release of thiol. In addition, structural modifications of DPCP enable the coupling rate to be tuned with a reaction constant of +3.68. Based on this chemistry, triple labelling was demonstrated by treating an N-terminal cysteine peptide with DPCP-Cl followed by thiol-maleimide and tyrosine-diazonium couplings in one pot. We anticipate that the DPCP motif will be a useful toolkit for multiple bioconjugation.

Graphical abstract: A unique reaction of diphenylcyclopropenone and 1,2-aminothiol with the release of thiol for multiple bioconjugation

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D2CC06419G
Article type
Communication
Submitted
27 Nov 2022
Accepted
11 Jan 2023
First published
12 Jan 2023

Chem. Commun., 2023,59, 1497-1500

Permissions

Request permissions

A unique reaction of diphenylcyclopropenone and 1,2-aminothiol with the release of thiol for multiple bioconjugation

S. Liu, H. Ye, L. Yi and Z. Xi, Chem. Commun., 2023, 59, 1497 DOI: 10.1039/D2CC06419G

To request permission to reproduce material from this article, 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 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