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Questions and Answers
Which of the following is responsible for halogenation in biosynthesis?
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?
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?
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
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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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