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Wang, Peng

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Wang

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Peng

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Wang, Peng
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    Production of Stealthin C Involves an S–N-Type Smiles Rearrangement
    (American Chemical Society (ACS), 2017) Wang, Peng; Hong, Gloria J.; Wilson, Matthew; Balskus, Emily
    The kinamycin family of aromatic polyketide natural products contains an atypical angucycline ring system substituted with a diazo group. The enzymatic chemistry involved in constructing both of these structural features has been largely unexplored. Here we report the in vivo and in vitro production of seongomycin, a shunt product from this pathway, and stealthin C, a proposed biosynthetic precursor to the kinamycins. We show that a single enzyme, the flavin-dependent monooxygenase AlpJ, can generate these metabolites from N-acetyl-l-cysteine and l-cysteine, respectively, and that the synthesis of stealthin C likely proceeds via a nonenzymatic S–N-type Smiles rearrangement. This unexpected route to stealthin C reveals a distinct approach to install aromatic amino groups in metabolites and raises questions about the intermediacy of this species in kinamycin production.
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    The Cremeomycin Biosynthetic Gene Cluster Encodes a Pathway for Diazo Formation
    (Wiley-Blackwell, 2015) Waldman, Abraham; Pechersky, Yakov; Wang, Peng; Wang, Jennifer X.; Balskus, Emily
    Diazo groups are found in a range of natural products that possess potent biological activities. Despite longstanding interest in these metabolites, diazo group biosynthesis is not well understood, in part because of difficulties in identifying specific genes linked to diazo formation. Here we describe the discovery of the gene cluster that produces the o-diazoquinone natural product cremeomycin and its heterologous expression in Streptomyces lividans. We have used stable isotope feeding experiments and in vitro characterization of biosynthetic enzymes to decipher the order of events in this pathway and establish that diazo construction involves latestage N–N bond formation. This work represents the first successful production of a diazocontaining metabolite in a heterologous host, experimentally linking a set of genes with diazo formation.