CHEM 109C Zhang CLAS, F10

Amino Acids I: Structure and Properties - KEY

1. What is the absolute configuration (R or S) at the -carbon in each of the
enantiomers of Alanine? Are they D or L amino acids?
O O HO O
H2N H3C
OH OH H2N H
CH3 = NH2 = CH3
(S)-Ala (L)-Ala (naturally occurring)
O O HO O
H2N H3C
OH OH H NH2
CH3 = NH2 = CH3
(R)-Ala (D)-Ala

2. Which isomer (R)-Asp or (S)-Asp is D-Asp?

[Asp = Aspartic Acid, Aspartate]

HO O O O
HOOCH2C H2N
H NH2 OH OH
CH2COOH = NH2 or CH2COOH
(D)-Asp (R)-Asp

3. Name an amino acid besides threonine = Thr that has more than one asymmetric
center.
Isoleucine = Ile
CH3 O
H3C
OH
NH2
Ile the - and -carbons are stereocenters.

4. Lysine has the following pKas -COOH = 2.18, -NH3+ = 8.95, side chain, R =
10.79. Draw principle species at each of the following solution pHs: 0, 4, 10, and
13.
Lysine = Lys
O
+
H3N
OH pKa = 2.18
pKa = 10.79
+
NH3
pKa = 8.95
@ pH = 0 pH < all pKas so everything is in acidic form

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CHEM 109C Zhang CLAS, F10
Amino Acids I: Structure and Properties - KEY
O
+
H3N
OH
+
NH3
@ pH = 4 pH < pKas of side chain and -NH3+ so these are in acidic form,
but it is > pKa or -COOH, so that is in basic form
O
+
H3N -
O
+
NH3
@ pH = 10 < pKa of side chain only, so it is in acid form, others are in basic
form
O
+
H3N -
O
NH2
@ pH = 13 > all pKas, so everything is in basic form
O
H2N -
O
NH2

5. Calculate the pI of
a. Lys
From the structure in #4 we see that there are two NH3+ groups that
are similar
pI = 10.79 + 8.95 = 9.87
2
b. Asp
From the structure in #2 we see that there are two COOH groups that
are similar
pI = 2.09 + 3.86 = 2.98, actually the lowest pI
2

6. Which amino acid has the highest pI value?

Highest pI largest average between pKas look for amino acid with
largest pKas
Arginine = Arg
pI = 9.04 + 12.48 = 10.76
2

7. Which amino acid has the greatest amount of negative charge @ pH = 6.20?
Greatest amount of negative charge most -COOH deprotonated
lowest -COOH pKa, most acidic amino acids

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CHEM 109C Zhang CLAS, F10
Amino Acids I: Structure and Properties - KEY
O
-
O -
O
+
O NH3 Asp at pH 6.20, pI = 2.98 lower pI, so more negative
O O

- -
O O
+
NH3 Glu at pH 6.20, pI = 3.22

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