CHEM 2425. Chapter 28. Biomolecules - Nucleic Acids (Homework) W

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CHEM 2425. Chapter 28.

Biomolecules_Nucleic Acids (homework) W


Short Answer

Exhibit 28-1
MATCH each of the following terms to a structure from the list below. There is only one correct structure for
each term and structures may be used more than once. Place the letter of the structure in the blank to the left
of the corresponding term.

A. Sanger dideoxy method B. GAUCGUAAA


C. Watson-Crick D. translation
E. F.

G. transcription H. Maxam-Gilbert method


I. AUGGCUGAG J. replication
K. L.

M. AGATCGCTC

1. _____ a pyrimidine nucleoside

2. _____ RNA base sequence with guanine at the 3' end.

3. _____ uridine

4. _____ a purine nucleoside

5. _____ DNA sequencing method for the human genome

6. _____ RNA base sequence complementary to the DNA base sequence which codes for LeuAlaPhe:

1 CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W


CTAGCATTT

7. _____ 2'-deoxyadenosine 5'-phosphate

8. _____ process by which mRNA directs protein synthesis

9. Describe, in general terms, the steps involved in the automated synthesis of the DNA sequence GCT.

10. Draw and label the four DNA nucleosides.

11. Draw and label a G-C base pair. Indicate all hydrogen bonds with a dashed line.

12. Draw and label an A-T base pair. Indicate all hydrogen bonds with a dashed line.

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13. Of the two sets of DNA base pairs, which would you expect to be stronger and why?

14. Draw and label the four RNA nucleosides.

15. Draw and label an A-U base pair. Indicate all hydrogen bonds with a dashed line.

16. What is the primary structural difference between RNA nucleotides and DNA nucleotides?

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17. Because of the structure of the RNA sugar-phosphate backbone, RNA is subject to base-promoted hydrolysis,
as shown below. Suggest a mechanism for base-promoted RNA hydrolysis.

18. While the Watson-Crick G-C and A-T base pairs are the most common, other non-standard base pairs are
encountered. Draw and label a G-U base pair. Indicate all hydrogen bonds with a dashed line.

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19. When DNA is replicated, the new chain is synthesized in what direction?

20. Give a one sentence definition of replication.

21. Give a one sentence definition of transcription.

22. Give the single letter amino acid sequence that is coded for by the following segment of DNA coding
strand (sense strand)?

(5') GCA—TTT—CTA—ACT—TGA—GGG (3')

23. Describe the difference between a 2',3'-dideoxyribonucleoside triphosphate and 2'-deoxyribonucleoside


triphosphate.

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24. Identify any errors in the figure shown below.

25. Consider the following diagram.

1.) Label the anticodon


2.) Label the position of attachment of the amino acid

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3.) Draw the structure of the amino acid that would be attached
4.) Indicate the corresponding mRNA codon

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CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W
Answer Section
SHORT ANSWER

1. ANS:
E

PTS: 1
2. ANS:
I

PTS: 1
3. ANS:
E

PTS: 1
4. ANS:
L

PTS: 1
5. ANS:
A

PTS: 1
6. ANS:
B

PTS: 1
7. ANS:
K

PTS: 1
8. ANS:
D

PTS: 1
9. ANS:

Step 1 Attachment of 5'-DMT-N-benzoyl-2'-deoxyaguanosine to the polymer support by a 3'


ester linkage.
Step 2 Deprotection of the 5'-hydroxyl by cleavage of the DMT ether with dichloroacetic acid in
CH2CL2.
Step 3 Phosphite formation between the free 5'-hydroxyl of the polymer-bound N-protected
8 CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W
2'-deoxyguanosine and the phosphoramidite protected 5'-DMT-2'-deoxycytidine in the
presence of tetrazole followed by oxidation to the phosphate triester with I2.
Step 4 Repeat step 2 to deprotect the 5'-hydroxyl of the polymerGC.
Step 5 Repeat step 3 to form the phosphate triester between 5'-hydroxyl of 2'-deoxycytidine
residue and phosphoramidite protected 5'-DMT-N-benzoyl-2'-deoxythymidine.
Step 6 Cleave all protecting groups from the heterocyclic bases from the phosphates, as well as
cleave the ester bond holding the DNA to the silica by treatment with aqueous ammonia.

PTS: 1
10. ANS:

PTS: 1
11. ANS:

9 CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W


PTS: 1
12. ANS:

PTS: 1
13. ANS:
The G-C base pair is the stronger of the two as it has three hydrogen bonds whereas the A-T base pair has
only two.

PTS: 1
14. ANS:

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PTS: 1
15. ANS:

PTS: 1
16. ANS:

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As their names suggest, RNA bases are attached to ribose sugars while DNA bases are attached to
deoxyribose sugars. The difference is a lack of the 2' hydroxyl group in the sugar backbone of the DNA
nucleotides.

PTS: 1
17. ANS:

PTS: 1
18. ANS:

12 CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W


PTS: 1
19. ANS:
As DNA is replicated, the new chain is synthesized in the 5' to 3' direction.

PTS: 1
20. ANS:
Replication is the process by which identical copies of DNA are made.

PTS: 1
21. ANS:
Transcription is the process by which genetic messages are read and carried out of the cell to ribosomes,
where protein synthesis occurs.

PTS: 1
22. ANS:

The mRNA strand is: (Remembering U replaces T in RNA.)

(5') GCA—UUU—CUA—ACU—UGA—GGG (3')

The amino acid squence is: (UGA is a stop codon.)

Three-letter code:

Ala—Phe—Leu—Thr

One-letter code (See Table 26.1.)

A—F—L—T

PTS: 1
23. ANS:

13 CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W


A 2'-deoxyribonucleoside triphosphate is one in which the 2' OH group is missing from ribose. A
2',3'-dideoxyribonucleoside triphosphate is one in which both 2' and 3' OH groups are missing from ribose.
In DNA sequencing the significance of this removal is that DNA replication stops at this nucleotide since the
3’ —OH needed for the continued addition of nucleotides.

PTS: 1
24. ANS:
Two errors:
1.) In the left lower nucleotide, the base is indicated as U (uracil) which only appears in RNA.
2.) In the left upper nucleotide, the sugar is ribose which only occurs in RNA.

PTS: 1
25. ANS:

Amino acid: Valine

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mRNA codon: GUA

PTS: 1

15 CHEM 2425. Chapter 28. Biomolecules_Nucleic Acids (homework) W

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