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Title page for ETD etd-05192009-102618

Type of Document Dissertation
Author Hu, Yunfeng
URN etd-05192009-102618
Title Microbial biosynthesis of benzodiazepines and nitrosugar containing natural products
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Brian O. Bachmann Committee Chair
David W. Wright Committee Member
Michael P. Stone Committee Member
Richard N. Armstrong Committee Member
  • nitrosugar
  • benzodiazepines
  • biosynthesis
  • natural products
Date of Defense 2009-05-05
Availability unrestricted
The biosyntheses of benzodiazepines and nitrosugar containing natural products in actinomycetes were investigated. The first biosynthetic gene cluster of a benzodiazepine natural product was identified in the genome of the anthramycin producer Streptomyces refuineus. The functional boundaries of this biosynthetic gene cluster were validated via a series of targeted gene disruptions and chemical complementation studies were utilized to elucidate aspects of the anthramycin biosynthetic pathway. In a separate study, heterologous expression of the anthramycin biosynthetic gene cluster demonstrated the completeness of the putative gene cluster and shed light on a potential temperature dependent regulation phenomenon. Lastly, the biosynthesis of nitrosugar natural products was investigated. A novel nitrososynthase was putatively identified in the previously sequenced biosynthetic gene cluster of everninomycin via comparative genomics and the biochemical function of this oxidase was demonstrated in the conversion a TDP-aminosugar to a TDP-nitrososugar via a hydroxylamine intermediate.
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