Neighboring group migration in enzyme-mediated halohydrin formation.
Enzymatic halogenation of the double bond in allyl halides was influenced by intramolecular participation of the allylic halogen in the substrate molecule. Migration of the allylic halogen to the central carbon atom was observed in the enzymatic chlorination of allyl bromide, but not in the enzymatic bromination of allyl chloride. These results parallel the neighboring group effects observed for non-enzymatic halogenation of allyl halides.
D000498:Allyl Compounds; D002711:Chloride Peroxidase / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006219:Halogens; D007700:Kinetics; D010544:Peroxidases / Q000378:metabolism*; D013329:Structure-Activity Relationship
D000498:Allyl Compounds; D006219:Halogens; D010544:Peroxidases; D002711:Chloride Peroxidase