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Published on: May 21, 2019
Light-Activated COS/H2S Donation from Photocaged Thiocarbamates
Yu Zhao1, Sarah G Bolton1, Michael D Pluth1
1Department of Chemistry and Biochemistry, Material Science Institute, Institute of Molecular Biology, University of Oregon , Eugene, Oregon 97403, United States.
Organic Letters
|April 18, 2017
Summary
Researchers developed photoactivated molecules for controlled hydrogen sulfide (H2S) release. These compounds, using a photocleavable group, deliver H2S via carbonyl sulfide (COS) hydrolysis, enabling bio-orthogonal applications.
Area of Science:
- Biochemistry
- Chemical Biology
- Organic Chemistry
Background:
- Hydrogen sulfide (H2S) is a crucial biomolecule with diverse physiological roles.
- The development of precise tools for H2S delivery is essential for biological research.
- Existing methods for H2S release may lack specificity or control.
Purpose of the Study:
- To design and synthesize novel photoactivatable molecules for controlled H2S release.
- To investigate the mechanism of H2S generation from caged thiocarbamates.
- To establish the utility of these donors for bio-orthogonal H2S delivery.
Main Methods:
- Utilizing the o-nitrobenzyl photocleavable group to cage thiocarbamates.
- Investigating the release of carbonyl sulfide (COS) upon photoactivation.
- Studying the hydrolysis of COS to H2S catalyzed by carbonic anhydrase (CA).
Main Results:
- Successfully synthesized o-nitrobenzyl-caged thiocarbamates as H2S donors.
- Demonstrated photoactivated release of COS, which is subsequently converted to H2S.
- Confirmed the bio-orthogonal nature of the H2S release mechanism.
Conclusions:
- o-Nitrobenzyl-caged thiocarbamates represent a viable platform for photoactivated H2S donors.
- This approach allows for controlled and specific release of H2S in biological systems.
- The developed system offers a promising tool for studying H2S biology.
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