Bio-orthogonal “click-and-release” donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H2S)

Andrea K. Steiger; Yang Yang; Maksim Royzen; Michael D. Pluth

doi:10.1039/C6CC09547J

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Bio-orthogonal “click-and-release” donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H₂S)†

Andrea K. Steiger,

‡^a Yang Yang,‡^b Maksim Royzen*^b and Michael D. Pluth

*^a

Author affiliations

* Corresponding authors

^a Materials Science Institute, Institute of Molecular Biology, Department of Chemistry and Biochemistry, University of Oregon, Eugene, OR 97403, USA
E-mail: pluth@uoregon.edu

^b Department of Chemistry, University at Albany, SUNY, 1400 Washington Avenue, Albany, NY 12222, USA
E-mail: mroyzen@albany.edu

Abstract

Hydrogen sulfide (H₂S) is an important biomolecule with high therapeutic potential. Here we leverage the inverse-electron demand Diels–Alder (IEDDA) click reaction between a thiocarbamate-functionalized trans-cyclooctene and a tetrazine to deliver carbonyl sulfide (COS), which is quickly converted to H₂S by the uniquitous enzyme carbonic anhydrase (CA), thus providing a new strategy for bio-orthogonal COS/H₂S donation.

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Article information

DOI: https://doi.org/10.1039/C6CC09547J
Article type: Communication
Submitted: 30 Nov 2016
Accepted: 20 Dec 2016
First published: 22 Dec 2016
This article is Open Access

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Chem. Commun., 2017,53, 1378-1380

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Bio-orthogonal “click-and-release” donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H₂S)

A. K. Steiger, Y. Yang, M. Royzen and M. D. Pluth, Chem. Commun., 2017, 53, 1378 DOI: 10.1039/C6CC09547J

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