Sunday, November 12, 2023

Is it possible to make a beta-lactam with sulfur instead of oxygen? Do polysulfide medicines exist?

I haven't been able to find an example, but it is possible for sulfur to have a double bond with a carbon atom. Sulfur, in contrast to oxygen, tends to reduce rather than oxidize. Antioxidants are generally good. The more sulfur a molecule has, the greater chance it has of being an antioxidant. 



In order to replace the oxygen with sulfur in the beta-lactam ring, that sulfate group in the lower right would probably need to be replace with something smaller. 

Wikipedia says

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Compounds with double bonds between carbon and sulfur are relatively uncommon, but include the important compounds carbon disulfide, carbonyl sulfide, and thiophosgene. 

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On a side note, sulfur shows up in many retroviral drugs. 

If polysulfide compounds similar to polyketides exist, they could have medicinal use. Imagine if all the carbon-oxygen double bonds below were replaced with sulfur.




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