Issue 44, 2023

Mechanism of rate controllability of water-soluble bifunctional cyclooctadiynes through cation-anion interactions

Abstract

Click reactions are used for chemoselective functionalization in many research fields. Despite the utility of small, bioinert azide groups as a counterpart, applications of strain-promoted alkyne-azide cycloaddition (SPAAC) reactions for this purpose are still limited by slow reaction kinetics. Here, we report ion-pair-guided reaction rate enhancement by the use of water-soluble cyclooctadiynes (WS-CODYs) composed of bifunctional strained alkynes and polar side chains. Arrhenius plot analysis revealed that the rate enhancement by WS-CODYs is due to a kinetic salt effect between the polar substituents and the target azide. We demonstrate the utility of these compounds for rapid protein labelling and isoelectric point-dependent labelling.

Graphical abstract: Mechanism of rate controllability of water-soluble bifunctional cyclooctadiynes through cation-anion interactions

Supplementary files

Article information

Article type
Communication
Submitted
20 Mar 2023
Accepted
24 Apr 2023
First published
03 May 2023

Chem. Commun., 2023,59, 6678-6681

Mechanism of rate controllability of water-soluble bifunctional cyclooctadiynes through cation-anion interactions

M. Yoshinaga, F. Sato, K. Kitagawa, N. Yokota, S. Sasaki, M. Takeuchi, H. Tsugawa, K. Sugahara, S. Mori and M. Tera, Chem. Commun., 2023, 59, 6678 DOI: 10.1039/D3CC01356A

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