Bioorganic Chemistry I—First Midterm Exam.

(108 points) 2019/11/14

I. Single choice question (40 points)

1. Select the oligopeptide chain listed below to form an alpha-helical structure at the specified pH:
選擇下面列出的寡肽鏈以在指定的 pH 下形成 α-螺旋結構：
a. polyalanine，pH 7.0
b. polyaspartic acid，pH 7.0
c. polyproline，pH 7.0
d. polylysine，pH 7.0
2. Which of the following is the most important factor in determining the secondary structure of a protein?
在確定蛋白質的二級結構時，以下哪一項是最重要的因素？
a. The number of disulfide bonds.
b. The amino acid sequence of the protein (primary structure).
c. The force of protein molecules and solvents.
d. The source of the protein.
3. Assuming that the reaction rate of one enzyme is 15 μmole/min at [S] = KM, what is the Vmax of this
reaction?
a. 30 μM/min b. 7.5 μM/min c. 4.5 μM/min d. 15 μM/min
4. The following statements about the role of enzymes, which is true?
以下關於酶作用的陳述，何者為真？
a. The binding of the enzyme to the substrate is tighter than the transition state.
b. The binding of the enzyme to the product is tighter than in the transition state.
c. The binding of the enzyme to the transition state is tighter than when it is combined with the ES
complex.
d. The enzyme has the same affinity for the substrate and the product.
5. Which of the following statements about isozymes is correct?
下列關於同工酶的陳述中哪些是正確的？
a. They all catalyze the same chemical reaction.
b. They have the same four-level structure.
c. They are distributed in tissues and organs.
d. They have the same enzyme classification and number.
6. Which of the following amino acids has a hydrophobic branch at pH = 7.0.
a. aspartic acid b. Lysine c. serine d. Proline
7. Which of the following amino acids has a polar uncharged branch at pH = 7.0.
a. Phenylalanine b. serine c. Leucine d. Proline
8. Which of the following amino acids is not an α-amino acid.
a. Proline b. Cysteine c. Tyrosine d. Tryptophan
9. Which two functional groups of the amino acid can form a peptide bond.
a. Branched carboxyl group and α-amino group.
b. Branched carboxyl groups and branched amine groups.
c. α-carboxyl and branched amine groups.
d. α-carboxyl and α-amino.
10. Which of the following amino acids is selected has two chiral centers.
a. Proline b. Cysteine c. Threonine d. Lysine
II. Short answer question (60 point, each 4 points)
1. Draw following question (10 points)
a. Draw the primary sequence
WHAYM
b. Label the hydrogen bond pair of WGGFM if this peptide is an α-helix.
c. Chymotrypsin is studied to hydrolyze specific amide bond after Trp, Phe, or Tyr. Point out the bond of
WGGFM to be hydrolyzed by chymotrypsin.

2. Edman degradation is applied to study the primary sequence of peptide. Write out the reaction
mechanism of this degradation with Phenylisothiocyanate(PITC). (10 points)

3. Robert Bruce Merrifield developed solid-phase peptide synthesis (SPPS). This method including two
important steps, including de-protection of N-Fmoc with piperidine, and amide-bond formation with
DIC/HOBt. Write out the reaction mechanism for following: (10 points)

:B O
H O H
H
O N N HO N
R H R
O piperidine O
(a)

N
N C N O N
O
+ H2N R2 N
R2 R1 N
R1 O H OBt HOBt O H
H
H O H
N C N N C N N C N N C N
O O R1 OBt O
O
R1 O R1 O H2N
R1 O R2
OBt
O O O
H R2
R2 N C N
R1 N R1 N
H
(b) H H

4. Draw the structure of porphine and porphine with Fe2+(heme) as center metal ion. Point out the O2 (sp2)
and CO (sp) bind to heme in bend and linear structure. (8 points)
 NH N
Fe2+
N HN

5. Draw the following reaction mechanism: (20 points)

O H H O
- +
NH2
2e + H NH2
NAD+ to NADH
N N
R R
Type I O O O H H O
- - +
NH2 e NH2 e NH2 H NH2
N N N N
R R R R
Type II O O O
H H H H O
- +
NH2 e NH2 H NH2 NH2
N N N N
R R R R
(a)
O O
H
N
NH 2e- + 2H+ N
NH
FAD to FADH2
N N O N N O
H
R R
Type I O O O
N
N
NH e- N
NH H+ NH e-
N N O N N O N N O
H H
R R R
O O
H
N + N
NH H NH

N N O N N O
H H
R R
Type II O O O
H
N
N
NH e- N
NH H+ NH e-
N N O N N O N N O
R R R
O O
H H
N + N
NH H NH

N N O N N O
H
R R
(b)
姓名: 學號: 系級:

6. Point out the arrows in the following enzyme mechanism: (10 points)
His95 His95

H H
O O H OH O OH OH
H N N H N N
O O
OPO32- OPO32-
Glu165 Glu165
His95 His95

H H
O OH O H O O O
H
N N H N N
OH OH
OPO32- OPO32-
Glu165 His95 Glu165

O O O
H N N
OH
OPO32-
Glu165