Biocompatible photoinduced CuAAC using sodium pyruvate

Jaepil Jeong; Grzegorz Szczepaniak; Saigopalakrishna S. Yerneni; Francesca Lorandi; Hossein Jafari; Sushil Lathwal; Subha R. Das; Krzysztof Matyjaszewski

doi:10.1039/D1CC05566F

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Biocompatible photoinduced CuAAC using sodium pyruvate†

Jaepil Jeong,

^a Grzegorz Szczepaniak,

*^ab Saigopalakrishna S. Yerneni,^c Francesca Lorandi,

^a Hossein Jafari,^a Sushil Lathwal,^a Subha R. Das

*^ad and Krzysztof Matyjaszewski

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, USA
E-mail: gszczepa@andrew.cmu.edu, srdas@andrew.cmu.edu, matyjaszewski@cmu.edu

^b University of Warsaw, Faculty of Chemistry, Pasteura 1, 02-093 Warsaw, Poland

^c Department of Biomedical Engineering, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, USA

^d Center for Nucleic Acids Science & Technology, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, USA

Abstract

Sodium pyruvate, a natural intermediate produced during cellular metabolism, is commonly used in buffer solutions and media for biochemical applications. Here we show the use of sodium pyruvate (SP) as a reducing agent in a biocompatible aqueous photoinduced azide–alkyne cycloaddition (CuAAC) reaction. This copper(I)-catalyzed 1,3-dipolar cycloaddition is triggered by SP under UV light irradiation, exhibits oxygen tolerance and temporal control, and provides a convenient alternative to current CuAAC systems, particularly for biomolecular conjugations.

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Article information

DOI: https://doi.org/10.1039/D1CC05566F
Article type: Communication
Submitted: 01 Oct 2021
Accepted: 09 Nov 2021
First published: 12 Nov 2021

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Chem. Commun., 2021,57, 12844-12847

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Biocompatible photoinduced CuAAC using sodium pyruvate

J. Jeong, G. Szczepaniak, S. S. Yerneni, F. Lorandi, H. Jafari, S. Lathwal, S. R. Das and K. Matyjaszewski, Chem. Commun., 2021, 57, 12844 DOI: 10.1039/D1CC05566F

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Chemical Communications

Biocompatible photoinduced CuAAC using sodium pyruvate†

Abstract

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Biocompatible photoinduced CuAAC using sodium pyruvate

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