Friday Fun: Biocompatible Hydrogenation

Bacteria have always fascinated me; as an organic chemist, the dream of realizing new anti-bacterial medications always occupies a bit of one's brain. But what if we were able to harness more beneficial bacterial traits for synthesis? Obviously, fermentation broths produce many of our best molecules, but we don't always look at the other secondary metabolites - gases, for example - produced by bacterial metabolism.

Well, the Balskus lab at Harvard aims to change that perception. Their lab slogan? "Microbes are Nature's synthetic chemists." As reported in Angew. Chem. Int. Ed. yesterday, their lab has identified a biocompatible palladium catalyst that uses the hydrogen gas produced by E. coli to drive hydrogenation of a variety of electron-poor alkenes and alkynes:

Source: Balskus Lab | Angew. Chem. Int. Ed., 2014

This reaction takes place in aqueous culture, in the presence of oppressive concentrations of nitrogen and glucose, yet still produces decent yields (63-95%) of reduced products. One could argue with somewhat high catalyst loading (8%) and low reaction concentration, but as a proof-of-concept it's pretty cool. Bacteria produce hundreds of interesting volatile metabolites - among them sulfur dioxide, indole, and isoprene - and it'll be neat to see if more of these byproducts can be co-opted for synthetic chemistry.

Happy Friday,

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