Biochemistry IFall 1994Koni StoneExam 1September 28, 1994
1. Draw the structures for the following amino acids:
2. Runner Ron was in the starting blocks for the BIG 100 meter race. Just before thegun went 'Bang', Ron took a series of quick short breaths.
a. Explain why he did this in terms of blood pH.
b. While he was running for the GOLD, Runner Ron's muscles were making anabudance of lactic acid. Explain the effect of this added lactic acid to Ron'sblood pH.
3. Fill in the following table showing the components in the structural hierarchy of acell. Also, list the type of bonds most likely to be found in each of the structures.
4. Runner Ron overdid it and is now reaching for the contents of his medicine chest. He grabbed Naprosen for himself and gave his buddy Aleve. These two painmedications both contain naproxen sodium as the active ingredient and naproxencontains a carbon with four different substituents. Explain why it takes 200 mg ofNaprosen and only 100 mg of Aleve to effect the same pain relief.
5. Thalidomide was developed in the 1950's to prevent nausea during pregnancy. Thedrug was never approved in the US, as it was found to cause fetal limb abnormalities. In 1979, investigators found that only one enantiomer is tetratogenic (causes limbabnormalities) in rats, and that the other isomer may be a useful therapeutic agent. This is especially of interest because Thalidomide has been found to inhibit thereplication of the AIDs virus. Other groups have found that both isomers aretetratogenic in rabbits. Also, it has been found that both of the pure enantiomers can
racemize at physiological pH, suggesting that both isomers are potentially tetratogenic.
a.Given the structure of thalidomide below, circle any chiral carbons.
b. Put a square around the funcitonal groups present, and name them.
6. Acetylcholine is a potent neurotransmittor. Concentrations in the synapses betweennerves is regulated by the enzyme acetocholinesterase. This enzyme degradesacetocholine to choline and actetic acid. The acetic acid then dissociates to acetateion and hydrogen ion. Calculate the amount of acetylcholine present in 12 ml if the addition of acetylcholinesterase decreases the pH from 7.2 to 6.8.
7. What is the pH of a solution made by adding 8 ml of 6M KOH to 995 ml of water.
8. Acetic acid is a weak acid and can be used to prepare buffer solutions. If 1L of .1Macetic acid has a starting pH of 5.2, and then an amount of 1M HCl is added to thisbuffer to change the pH to 4.5, how much acid has been added?
9. Give the names, three letter codes and one letter codes for the following aminoacids.
10. Catechol is a toxic substance found in cigarette tar, and its structure is shownbelow. The pKa of catechol is approximately 9.4. If the pH of the lung is 7.2, will catechol be absorbed by the lung cells? Explain your answer.
11. Water and oil are not miscible. However, if you shake the bottle of salad dressing,a delicous emulsion is formed. Explain the dissolution of oil in water in terms ofthermodynamics.
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