Heterocyclic Aromatic N-Oxidation in the Biosynthesis of Phenazine Antibiotics from Lysobacter antibioticus

Yangyang Zhao, Guoliang Qian, Yonghao Ye, Stephen Wright, Haotong Chen, Yuemao Shen, Fengquan Liu, Liangcheng Du

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Heterocyclic aromatic N-oxides often have potent biological activities, but the mechanism for aromatic N-oxidation is unclear. Six phenazine antibiotics were isolated from Lysobacter antibioticus OH13. A 10 gene cluster was identified for phenazine biosynthesis. Mutation of LaPhzNO1 abolished all N-oxides, while non-oxides markedly increased. LaPhzNO1 is homologous to Baeyer-Villiger flavoproteins but was shown to catazlye phenazine N-oxidation. LaPhzNO1 and LaPhzS together converted phenazine 1,6-dicarboxylic acid to 1,6-dihydroxyphenazine N5,N10-dioxide. LaPhzNO1 also catalyzed N-oxidation of 8-hydroxyquinoline.

Original languageEnglish (US)
Pages (from-to)2495-2498
Number of pages4
JournalOrganic Letters
Volume18
Issue number10
DOIs
StatePublished - May 20 2016

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Lysobacter
biosynthesis
antibiotics
Biosynthesis
Anti-Bacterial Agents
Cyclic N-Oxides
Oxidation
Oxides
oxidation
Oxyquinoline
Flavoproteins
oxides
dicarboxylic acids
Multigene Family
mutations
activity (biology)
Bioactivity
dioxides
genes
Genes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Heterocyclic Aromatic N-Oxidation in the Biosynthesis of Phenazine Antibiotics from Lysobacter antibioticus. / Zhao, Yangyang; Qian, Guoliang; Ye, Yonghao; Wright, Stephen; Chen, Haotong; Shen, Yuemao; Liu, Fengquan; Du, Liangcheng.

In: Organic Letters, Vol. 18, No. 10, 20.05.2016, p. 2495-2498.

Research output: Contribution to journalArticle

Zhao, Yangyang ; Qian, Guoliang ; Ye, Yonghao ; Wright, Stephen ; Chen, Haotong ; Shen, Yuemao ; Liu, Fengquan ; Du, Liangcheng. / Heterocyclic Aromatic N-Oxidation in the Biosynthesis of Phenazine Antibiotics from Lysobacter antibioticus. In: Organic Letters. 2016 ; Vol. 18, No. 10. pp. 2495-2498.
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