Halogenated natural products have unique properties.
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Questions and Answers

Which of the following is responsible for halogenation in biosynthesis?

  • Halide ions
  • Electrophilic halogenating species (correct)
  • Hypo-chlorous acid
  • Amino groups
  • What is the first step in the biosynthesis of pyrrolnitrin?

  • Hydrogen bonding with a nearby amino group
  • Enzyme-catalyzed oxidation of halide ions
  • Enzyme-catalyzed chlorination of tryptophan (correct)
  • Enzyme-catalyzed halogenation of pyrrolnitrin
  • How is hypo-chlorous acid activated to chlorinate tryptophan?

  • By enzyme-catalyzed oxidation of halide ions
  • By hydrogen bonding with a nearby amino group (correct)
  • By direct interaction with tryptophan
  • By enzyme-catalyzed halogenation of pyrrolnitrin
  • Study Notes

    • Halogenated natural products have unique properties.
    • The biosynthetic origin of halogenation was a scientific puzzle.
    • Recent studies have revealed the biological halogenating agents and enzymes responsible for halogenation.
    • Halogenation can occur through multiple pathways.
    • Many halogenase enzymes use electrophilic halogenating species produced by oxidation of halide ions.
    • The biosynthesis of pyrrolnitrin begins with enzyme-catalyzed chlorination of tryptophan.
    • The halogenase enzyme uses hypo-chlorous acid as an electrophilic chlorinating agent.
    • Hydrogen bonding with a nearby amino group activates HOCl to chlorinate tryptophan.
    • 7-chlorotryptophan is produced, which undergoes subsequent conversion to pyrrolnitrin.
    • Pyrrolnitrin is formed through additional enzyme-catalyzed processes, including a second biochemical chlorination.

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    Description

    Test your knowledge on the fascinating world of halogenated natural products with this quiz! Discover the unique properties of these compounds, learn about the scientific puzzle of their biosynthetic origin, and explore the multiple pathways through which halogenation can occur. Explore the latest research on the biological halogenating agents and enzymes responsible for halogenation and dive into the specific case of the biosynthesis of pyrrolnitrin. Challenge yourself to understand the role of halogenase enzymes and electroph

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