Matsuda_2014_J.Am.Chem.Soc_136_15326

Reference

Title : Complete biosynthetic pathway of anditomin: nature's sophisticated synthetic route to a complex fungal meroterpenoid - Matsuda_2014_J.Am.Chem.Soc_136_15326
Author(s) : Matsuda Y , Wakimoto T , Mori T , Awakawa T , Abe I
Ref : Journal of the American Chemical Society , 136 :15326 , 2014
Abstract :

Anditomin and its precursors, andilesins, are fungal meroterpenoids isolated from Aspergillus variecolor and have unique, highly oxygenated chemical structures with a complex bridged-ring system. Previous isotope-feeding studies revealed their origins as 3,5-dimethylorsellinic acid and farnesyl pyrophosphate and suggested the possible involvement of a Diels-Alder reaction to afford the congested bicyclo[2.2.2]octane core structure of andilesins. Here we report the first identification of the biosynthetic gene cluster of anditomin and the determination of the complete biosynthetic pathway by characterizing the functions of 12 dedicated enzymes. The anditomin pathway actually does not employ a Diels-Alder reaction, but involves the nonheme iron-dependent dioxygenase AndA to synthesize the bridged-ring by an unprecedented skeletal reconstruction. Another dioxygenase, AndF, is also responsible for the structural complexification, generating the end product anditomin by an oxidative rearrangement.

PubMedSearch : Matsuda_2014_J.Am.Chem.Soc_136_15326
PubMedID: 25216349
Gene_locus related to this paper: emeva-andm

Related information

Substrate DHDMP
Gene_locus emeva-andm

Citations formats

Matsuda Y, Wakimoto T, Mori T, Awakawa T, Abe I (2014)
Complete biosynthetic pathway of anditomin: nature's sophisticated synthetic route to a complex fungal meroterpenoid
Journal of the American Chemical Society 136 :15326

Matsuda Y, Wakimoto T, Mori T, Awakawa T, Abe I (2014)
Journal of the American Chemical Society 136 :15326