TUTORIAL 19: AMINO ACIDS

19.1 Introduction to amino acids

At the end of the topic, students should be able to:
a) Draw the general structures of -amino acid.
b) Name a given amino acid according to the IUPAC nomenclature.
c) Define the terms zwitterions and isoelectric point(pI).
d) Draw the structures of a given amino acid:
i. In acidic medium
ii. In basic medium
iii. at pI.

1. (a) Define -amino acid.

(b) Name the following -amino acids using the IUPAC nomenclature:
NH2 CHCOOH
i.
CH(CH 3)2
NH2 CHCOOH
ii.
CH 2C6H5
NH2 CHCOOH
iii.
CH 2OH
NH2 CHCH2 CH2 COOH
iv.
COOH

2. Draw the structural formulae of the following compounds:

(a) 2-amino-4-methylpentanoic acid
(b) 2-amino-3-hydroxybutanoic acid
(c) 2-amino-3-methylpentanoic acid

3. (a) What is a zwitterion?

(b) Draw the structure of zwitterion for glycine, 2-aminoethanoic acid.

4. (a) What is meant by an isoelectric point?

(b) The isoelectric point of valine, 2-amino-3-methylbutanoic acid is 6. Predict the
structural formula of valine at
i. isoelectric point
ii. pH 12
iii. pH 1

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19.2 Chemical properties of amino acids

At the end of the topic, students should be able to:
a) Explain the reaction of amino acid with:
i. HCl
ii. NaOH
iii. NaNO2+HCl
iv. alcohol in the presence of an acid catalyst.
b) Describe the formation of peptide bond in dipeptides.

5. The structural formula of tyrosine is

COOH
HO CH2 CH
NH2
Predict the structural formula of the product formed when tyrosine reacts with
(a) NaOH(aq)
(b) HCl
(c) CH3OH in the presence of concentrated H2SO4, reflux
(d) NaNO2/HCl
6. (a) What is a peptide bond?
(b) Write the reaction between phenylalanine and glycine to produce a dipeptide
Phe-Gly.
H
H2N C COOH
H
CH2
H2N C COOH
H

Glycine Phenylalanine

7. (a) All amino acids are optically active except glycine, 2-aminoethanoic acid.
Explain this statement by using serine, 2-amino-3-hydroxypropanoic acid.
(b) Draw all possible stereoisomers of serine.

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8. The structure of amino acid CC is shown below.

NH2

CH2CHCOOH

CC

Compound CC reacts with dilute mineral acid to form DD, whereas EE is formed
when CC is treated with nitrous acid. Condensation two moles of CC forms a
dipeptide FF. Give IUPAC name for CC and draw the structure of its zwitterions.
Draw the structure of DD, EE and FF. Show the peptide bond in FF.

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OBJECTIVE QUESTIONS

1. The general structural formula of an amino acid is

A. H
R C H
NH2
B. H
R C OH
NH2
C. O
R C NH2
D. H
R C COOH
NH2

2. Which of the following statement is true about aminoethanoic acid?

A. It exhibits optical isomerism.
B. It exists in the anionic form in acidic solution.
C. It forms zwitterions in aqueous solution
D. It is soluble in non-polar solvents.

3. What species is produced when 2-aminopropanoic acid (pI = 6) is dissolved in a

solution with pH = 2?
A. H
-
H3C C COO
+
NH3
B. H
H3C C COOH
+
NH3
C. H
-
H3C C COO
NH2
D. H
H3C C COOH
NH2

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4. A protein is
A. a polysaccharide.
B. a polymer of amino acids.
C. a saturated ester of glycerol.
D. one of the units composing a nucleic acid.

5. Identify the peptide bond for the following polypeptide.

A B C

O O O
NH CH C NH CH C NH CH C
CH 2SH CH3 CH(CH 3)2

D
Summary of options
A B C D
I only I and II only II and III only I, II, and III

6. Consider the following amino acid:

H
NH2 CH2 CH2 CH2 CH2 C COOH pI = 9.74
NH2
Which of the following statement(s) is(are) true about the amino acid?
I. It is in anionic form in neutral solution.
II. It is in cationic form in acidic solution.
III. It exists in zwitterionic form in solution with pH 9.74

7.
H2N COOH

Bacteria requires p-aminobenzoic acid (PABA) in order to biosynthesise folic acid, an

essential growth factor. PABA
I. exists as a pair of optical isomers
II. reacts with aqueous NaOH to form a salt
III. reacts with hydrochloric acid to form a salt

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