RESUMO

Investigation of the metabolome of the ascomycete Annulohypoxylon truncatum led to the identification of novel oxygenated brasilane glycosides and the revision of the stereochemistry of the brasilane A octahydro-1H-indene core scaffold to trans. The bra biosynthetic gene cluster containing five genes (braA-braE) was identified and verified by heterologous expression experiments in Aspergillus oryzae demonstrating that BraC is a multifunctional P450 monooxygenase. In vitro studies of BraB revealed it to be a very rare fungal UDP-GlcNAc dependent N-acetylglucosamine transferase. UDP-glucose is also accepted as a donor, and a broad acceptor substrate tolerance for various primary and secondary alcohols was observed.

Assuntos

Glicosídeos/biossíntese , N-Acetilglucosaminiltransferases/metabolismo , Oxigênio/química , Sesquiterpenos/metabolismo , Ascomicetos/genética , Ascomicetos/metabolismo , Aspergillus oryzae/metabolismo , Sistema Enzimático do Citocromo P-450/genética , Glicosídeos/química , Família Multigênica , N-Acetilglucosaminiltransferases/genética , Sesquiterpenos/química , Estereoisomerismo , Especificidade por Substrato , Terpenos/química