In-insect synthesis of oxygen-doped molecular nanocarbons

Many functional molecules and materials have been produced using flask chemical reactions. Meanwhile, individual organisms, such as insects, have the potential to serve as natural, high-density cultivation equipment with multiple enzymes capable of complex reactions. However, research in this area has focused on the composition and reactivity of enzymes involved in biological reactions. Here, we report a unique "in-insect" unnatural product synthesis. Biotransformation using insect xenobiotic metabolism can selectively transform belt- and ring-shaped molecular nanocarbons into other difficult-to-prepare functional oxygen-doped derivatives. Cytochrome P450 variants are most likely the enzymes responsible for this reaction. Molecular dynamics simulations and quantum chemical calculations indicated a possible mode of substrate incorporation into the enzyme and an unconventional mechanism of direct oxygen insertion into carbon-carbon bonds.