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Stinky millipedes that swarm into houses at night in Japan may hold the key to speedy synthesis of chiral molecules useful for making pharmaceuticals, agrochemicals, and other chemical products. A team of researchers led by Yasuhisa Asano of Toyama Prefectural University found that Chamberlinius hualienensis, a millipede originally from Taiwan that invaded Japan in the 1980s, produces an enzyme called hydroxynitrile lyase that’s much faster at producing enantiomerically pure (R)-mandelonitrile than versions of the catalytic protein used in industry (Proc. Natl. Acad. Sci. USA 2015, DOI: 10.1073/pnas.1508311112). In millipedes, the enzyme produces smelly hydrogen cyanide from cyanohydrins to serve as a chemical weapon. But, Asano says, industrial chemists run the enzymatic reaction in reverse to make cyanohydrins to produce bulk chemicals, such as acrylamide, as well as drugs, such as clopidogrel, a platelet aggregation inhibitor. Researchers have studied hydroxynitrile lyases for about a century, typically sourcing them from bacteria and plants. The millipede enzyme is “by far the fastest” hydroxynitrile lyase reported to date, comments Anton Glieder, a researcher at Graz University of Technology, in Austria. Additionally, the highly specific production of (R)-mandelonitrile—with 99% enantiomeric excess—is “really astonishing,” he says. Industrial researchers will certainly want to consider the millipede enzyme, Glieder adds.
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