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
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
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter20: Carbohydrates
Section: Chapter Questions
Problem 20.82P
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Question
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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd319badf-f299-4b6f-b3b2-cb2f6660ee43%2F407ed42d-e786-43d5-981e-79ff541e75a4%2Fwoku2tl.jpeg&w=3840&q=75)
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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