Biosynthesis of sinapigladioside, an antifungal isothiocyanate from Burkholderia symbionts.

Dose B, Niehs SP, Scherlach K*, Shahda S, Flórez LV#, Kaltenpoth M, Hertweck C (2021) Biosynthesis of sinapigladioside, an antifungal isothiocyanate from Burkholderia symbionts. Chembiochem 22(11), 1920-1924.

*equal contribution #corresponding author

Abstract

Sinapigladioside is a rare isothiocyanate-bearing natural product from beetle-associated bacteria ( Burkholderia gladioli ) that may protect the beetle offspring against entomopathogenic fungi. The biosynthetic origin of sinapigladioside has been elusive, and little is known about bacterial isothiocyanate biosynthesis in general. On the basis of stable-isotope labeling, bioinformatics, and mutagenesis we identified the sinapigladioside biosynthesis gene cluster in the symbiont and found that an isonitrile synthase plays a key role in the biosynthetic pathway. Genome mining and network analyses indicate that related gene clusters are distributed across various bacterial phyla including producers of both nitriles and isothiocyanates. Our findings support a model for bacterial isothiocyanate biosynthesis by sulfur transfer onto isonitrile precursors.

Leibniz-HKI-Authors

Christian Hertweck
Kirstin Scherlach
Benjamin Dose
Sarah Niehs
Sophie Shahda

Identifier

doi: 10.1002/cbic.202100089

PMID: 33739557