Human white cells produce an enzyme called myeloperoxidase. This enzyme catalyzes the reaction between hydrogen peroxide and chloride ion to produce hypochlorous acid, HOCI, which reacts as if it were Cl*OH . When attacked by white cells, choles- terol gives a chlorohydrin as the major product. Me Me R white blood cells Me R Me | OH/ НО HO- CI Cholesterol Cholesterol chlorohydrin

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.29P
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Propose a mechanism for this reaction. Account for both its regioselectivity and stereoselectivity.

Human white cells produce an enzyme called myeloperoxidase. This enzyme catalyzes
the reaction between hydrogen peroxide and chloride ion to produce hypochlorous
acid, HOCI, which reacts as if it were Cl*OH . When attacked by white cells, choles-
terol gives a chlorohydrin as the major product.
Me
Me
R white blood
cells
Me
R
Me
| OH/
НО
HO-
CI
Cholesterol
Cholesterol chlorohydrin
Transcribed Image Text:Human white cells produce an enzyme called myeloperoxidase. This enzyme catalyzes the reaction between hydrogen peroxide and chloride ion to produce hypochlorous acid, HOCI, which reacts as if it were Cl*OH . When attacked by white cells, choles- terol gives a chlorohydrin as the major product. Me Me R white blood cells Me R Me | OH/ НО HO- CI Cholesterol Cholesterol chlorohydrin
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