1. Assign Cahn-Ingold-Prelog priorities to each of the substituent ...

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1. Assign Cahn-Ingold-Prelog priorities to each of the substituent groups attached to the double bonds substituted on the terminal pyrrole rings of bilirubin.

2. Use these priorities to draw geometrically correct structures for the Z,Z-isomer, the E,E-isomer, and an E,Z-isomer of bilirubin and label each.

3. Draw both the lactim and lactam forms for each of the terminal pyrrole rings of bilirubin and properly label each. Pay attention to the placement of the double bonds in the rings.

4. Suggest a reasonable mechanism by which photolysis of the Z,Z-isomer of bilirubin allows it to be changed into the E,E-isomer, and offer an explanation of why this change may occur.

5. Write a brief note to the publishers of Lenninger’s biochemistry text and The Merck Index clearly indicating what is wrong with the representation(s) of bilirubin that appear in their publications and suggesting the corrections that should be made to subsequent editions of these books.

6. Hemoglobin is a decomposition product of bilirubin. True or False?

7. Phototherapy involves the use of light to convert bilirubin into hemoglobin. True or False?
8. Which of the following bilirubin isomers is formed in the phototherapy process?
a) E,E
b) Z,Z
c) Z,E
d) E,Z

9. What is the actual physiological name of the E, E isomer?

10. Which other instance of protein biosynthesis do you see such cyclization/linearization occurring? Name the two compounds involved.

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1. Assign Cahn-Ingold-Prelog priorities to each of the substituent groups attached to the double bonds substituted on the terminal pyrrole rings of bilirubin.

The E-isomer exists when the two priority groups lie opposite of the double bond, while the Z-isomer exists when the two priority groups lie on the same side of the double bond.

According to the Cahn-Ingold-Prelog rules, the highest priority group should be the atom with the highest atomic number. Hence, it terms of priority, the Nitrogen attached to the double bond has the highest priority, followed by C, and H has the...

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