Abstract:
:The pyridine ring is a potent pharmacophore in alkaloid natural products. Nonetheless, its biosynthetic pathways are poorly understood. Rubrolones A and B are tropolone alkaloid natural products possessing a unique tetra-substituted pyridine moiety. Here, we report the gene cluster and propose a biosynthetic pathway for rubrolones, identifying a key intermediate that accumulates upon inactivation of sugar biosynthetic genes. Critically, this intermediate was converted to the aglycones of rubrolones by non-enzymatic condensation and cyclization with either ammonia or anthranilic acid to generate the respective pyridine rings. We propose that this non-enzymatic reaction occurs via hydrolysis of the key intermediate, which possesses a 1,5-dione moiety as an amine acceptor capable of cyclization. This study suggests that 1,5-dione moieties may represent a general strategy for pyridine ring biosynthesis, and more broadly highlights the utility of non-enzymatic diversification for exploring and expanding natural product chemical space.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Yan Y,Yang J,Yu Z,Yu M,Ma YT,Wang L,Su C,Luo J,Horsman GP,Huang SXdoi
10.1038/ncomms13083subject
Has Abstractpub_date
2016-10-07 00:00:00pages
13083issn
2041-1723pii
ncomms13083journal_volume
7pub_type
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