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27.3 27.3 Acid-Base Behavior of Amino Acid-Base Behavior of Amino Acids Acids

27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

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Page 1: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

27.327.3Acid-Base Behavior of Amino AcidsAcid-Base Behavior of Amino Acids

Page 2: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

RecallRecall

While their name implies that amino acids are While their name implies that amino acids are compounds that contain an —NHcompounds that contain an —NH2 2 group and a group and a

—CO—CO22H group, these groups are actually H group, these groups are actually

present as —NHpresent as —NH33++ and —CO and —CO22

–– respectively. respectively.

How do we know this?How do we know this?

Page 3: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Properties of GlycineProperties of Glycine

OO

OHOHHH22NNCHCH22CC••••

••••

••••

•••• ••••

––••••

OO

OOHH33NNCHCH22CC ••••

••••

•••• ••••++

The properties of glycine:The properties of glycine:

high melting point (when heated to 233°C it high melting point (when heated to 233°C it decomposes before it melts)decomposes before it melts)solubility: soluble in water; not soluble in solubility: soluble in water; not soluble in nonpolar solventnonpolar solvent

more consistent with thismore consistent with this than thisthan this

Page 4: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Properties of GlycineProperties of Glycine

––••••

OO

OOHH33NNCHCH22CC ••••

••••

•••• ••••++

The properties of glycine:The properties of glycine:

high melting point (when heated to 233°C it high melting point (when heated to 233°C it decomposes before it melts)decomposes before it melts)solubility: soluble in water; not soluble in solubility: soluble in water; not soluble in nonpolar solventnonpolar solvent

more consistent with thismore consistent with this

called a called a zwitterionzwitterion or or dipolar iondipolar ion

Page 5: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

The zwitterionic structure of glycine also follows The zwitterionic structure of glycine also follows from considering its acid-base properties.from considering its acid-base properties.

A good way to think about this is to start with the A good way to think about this is to start with the structure of glycine in strongly acidic solution, structure of glycine in strongly acidic solution, say pH = 1.say pH = 1.

At pH = 1, glycine exists in its protonated form At pH = 1, glycine exists in its protonated form (a monocation).(a monocation).

Page 6: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

The zwitterionic structure of glycine also follows The zwitterionic structure of glycine also follows from considering its acid-base properties.from considering its acid-base properties.

A good way to think about this is to start with the A good way to think about this is to start with the structure of glycine in strongly acidic solution, structure of glycine in strongly acidic solution, say pH = 1.say pH = 1.

At pH = 1, glycine exists in its protonated form At pH = 1, glycine exists in its protonated form (a monocation).(a monocation).

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

Page 7: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

Now ask yourself "As the pH is raised, which is Now ask yourself "As the pH is raised, which is the first proton to be removed? Is it the proton the first proton to be removed? Is it the proton attached to the positively charged nitrogen, or is attached to the positively charged nitrogen, or is it the proton of the carboxyl group?"it the proton of the carboxyl group?"

You can choose between them by estimating You can choose between them by estimating their respective ptheir respective pKKaas.s.

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

Page 8: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

Now ask yourself "As the pH is raised, which is Now ask yourself "As the pH is raised, which is the first proton to be removed? Is it the proton the first proton to be removed? Is it the proton attached to the positively charged nitrogen, or is attached to the positively charged nitrogen, or is it the proton of the carboxyl group?"it the proton of the carboxyl group?"

You can choose between them by estimating You can choose between them by estimating their respective ptheir respective pKKaas.s.

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

typical typical ammonium ammonium ion: pion: pKKaa ~9 ~9

typical typical carboxylic carboxylic acid: pacid: pKKaa ~5 ~5

Page 9: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

The more acidic proton belongs to the COThe more acidic proton belongs to the CO22H H

group. It is the first one removed as the pH is group. It is the first one removed as the pH is raised.raised.

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

typical typical carboxylic carboxylic acid: pacid: pKKaa ~5 ~5

Page 10: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

Therefore, the more stable neutral form of Therefore, the more stable neutral form of glycine is the zwitterion.glycine is the zwitterion.

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

typical typical carboxylic carboxylic acid: pacid: pKKaa ~5 ~5

––••••

OO

OOHH33NNCHCH22CC ••••

••••

•••• ••••++

Page 11: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

The measured pThe measured pKKaa of glycine is 2.34. of glycine is 2.34.

Glycine is stronger than a typical carboxylic acid Glycine is stronger than a typical carboxylic acid because the positively charged N acts as an because the positively charged N acts as an electron-withdrawing, acid-strengthening electron-withdrawing, acid-strengthening substituent on the substituent on the carbon. carbon.

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

typical typical carboxylic carboxylic acid: pacid: pKKaa ~5 ~5

Page 12: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of GlycineAcid-Base Properties of Glycine

––••••

OO

OOHH33NNCHCH22CC ••••

••••

•••• ••••++

The pThe pKKaa for removal of this proton is 9.60. for removal of this proton is 9.60.

This value is about the same as that for NHThis value is about the same as that for NH44++

(9.3).(9.3).

HOHO––––••••

OO

OOHH22NNCHCH22CC ••••

••••

•••• ••••

••••

A proton attached to N in the zwitterionic form of A proton attached to N in the zwitterionic form of nitrogen can be removed as the pH is increased nitrogen can be removed as the pH is increased further. further.

Page 13: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Isoelectric Point pIsoelectric Point pII

––••••

OO

OOHH33NNCHCH22CC ••••

••••

•••• ••••++

––••••

OO

OOHH22NNCHCH22CC ••••

••••

•••• ••••

••••

OO

OHOHHH33NNCHCH22CC++

••••

••••

•••• ••••

ppKKaa = 2.34 = 2.34

ppKKaa = 9.60 = 9.60

The pH at which the The pH at which the concentration of the concentration of the zwitterion is a zwitterion is a maximum is called the maximum is called the isoelectric pointisoelectric point. Its . Its numerical value is the numerical value is the average of the two average of the two ppKKaas.s.

The pThe pII of glycine is of glycine is 5.97.5.97.

Page 14: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Acid-Base Properties of Amino AcidsAcid-Base Properties of Amino Acids

One way in which amino acids differ is in respect One way in which amino acids differ is in respect to their acid-base properties. This is the basis for to their acid-base properties. This is the basis for certain experimental methods for separating and certain experimental methods for separating and identifying them.identifying them.

Just as important, the difference in acid-base Just as important, the difference in acid-base properties among various side chains affects the properties among various side chains affects the properties of the proteins that contain them.properties of the proteins that contain them.

Table 27.2 gives pTable 27.2 gives pKKaa and p and pII values for amino values for amino

acids with neutral side chains.acids with neutral side chains.

Page 15: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

CC CC

OO

OO––

HH

HH

HH33NN++

GlycineGlycineppKKa1a1 = = 2.342.34

ppKKa2a2 == 9.609.60

ppI I == 5.975.97

Page 16: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

AlanineAlanineppKKa1a1 = = 2.342.34

ppKKa2a2 == 9.699.69

ppI I == 6.006.00

HH33NN CC CC

OO

OO––

CHCH33

HH++

Page 17: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

ValineValineppKKa1a1 = = 2.322.32

ppKKa2a2 == 9.629.62

ppI I == 5.965.96

HH33NN CC CC

OO

OO––

CH(CHCH(CH33))22

HH++

Page 18: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

LeucineLeucineppKKa1a1 = = 2.362.36

ppKKa2a2 == 9.609.60

ppI I == 5.985.98

HH33NN CC CC

OO

OO––

CHCH22CH(CHCH(CH33))22

HH++

Page 19: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

IsoleucineIsoleucineppKKa1a1 = = 2.362.36

ppKKa2a2 == 9.609.60

ppI I == 5.985.98

HH33NN CC CC

OO

OO––

CHCH33CHCHCHCH22CHCH33

HH++

Page 20: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

MethionineMethionineppKKa1a1 = = 2.282.28

ppKKa2a2 == 9.219.21

ppI I == 5.745.74

HH33NN CC CC

OO

OO––

CHCH33SSCHCH22CHCH22

HH++

Page 21: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

ProlineProlineppKKa1a1 = = 1.991.99

ppKKa2a2 == 10.6010.60

ppI I == 6.306.30

HH22NN CC CC

OO

OO––

HH++

CHCH22HH22CCCCHH22

Page 22: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

PhenylalaninePhenylalanineppKKa1a1 = = 1.831.83

ppKKa2a2 == 9.139.13

ppI I == 5.485.48

HH33NN CC CC

OO

OO––

HH++

CHCH22

Page 23: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

TryptophanTryptophanppKKa1a1 = = 2.832.83

ppKKa2a2 == 9.399.39

ppI I == 5.895.89

HH33NN CC CC

OO

OO––

HH++

CHCH22

HH

NN

Page 24: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

AsparagineAsparagineppKKa1a1 = = 2.022.02

ppKKa2a2 == 8.808.80

ppI I == 5.415.41

HH33NN CC CC

OO

OO––

HH++

HH22NCCHNCCH22

OO

Page 25: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

GlutamineGlutamineppKKa1a1 = = 2.172.17

ppKKa2a2 == 9.139.13

ppI I == 5.655.65

HH33NN CC CC

OO

OO––

HH++

HH22NCCHNCCH22CHCH22

OO

Page 26: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

SerineSerineppKKa1a1 = = 2.212.21

ppKKa2a2 == 9.159.15

ppI I == 5.685.68

HH33NN CC CC

OO

OO––

CHCH22OHOH

HH++

Page 27: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.2Table 27.2 Amino Acids with Neutral Side ChainsAmino Acids with Neutral Side Chains

ThreonineThreonineppKKa1a1 = = 2.092.09

ppKKa2a2 == 9.109.10

ppI I == 5.605.60

HH33NN CC CC

OO

OO––

CHCH33CHOHCHOH

HH++

Page 28: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

Aspartic acidAspartic acidppKKa1a1 = = 1.881.88

ppKKa2a2 == 3.653.65

ppKKa3a3 == 9.60 9.60

ppI I == 2.772.77

HH33NN CC CC

OO

OO––

HH++

OCCHOCCH22

OO

––

For amino acids with acidic side chains, pI is the For amino acids with acidic side chains, pI is the average of paverage of pKKa1a1 and p and pKKa2a2..

Page 29: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

Glutamic acidGlutamic acidppKKa1a1 = = 2.192.19

ppKKa2a2 == 4.254.25

ppKKa3a3 == 9.67 9.67

ppI I == 3.223.22

HH33NN CC CC

OO

OO––

HH++

OO

OCCHOCCH22CHCH22––

Page 30: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

TyrosineTyrosineppKKa1a1 = = 2.202.20

ppKKa2a2 == 9.119.11

ppKKa3a3 == 10.07 10.07

ppI I == 5.665.66

HH33NN CC CC

OO

OO––

HH++

CHCH22

OHOH

Page 31: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

CysteineCysteine HH33NN CC CC

OO

OO––

CHCH22SSHH

HH++ ppKKa1a1 = = 1.961.96

ppKKa2a2 == 8.188.18

ppKKa3a3 == 10.28 10.28

ppI I == 5.075.07

Page 32: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

LysineLysine

ppKKa1a1 = = 2.182.18

ppKKa2a2 == 8.958.95

ppKKa3a3 == 10.5310.53

ppI I == 9.749.74

HH33NN CC CC

OO

OO––

HH++

CHCH22CHCH22CHCH22CHCH22NNHH33

++

For amino acids with basic side chains, pI is the For amino acids with basic side chains, pI is the average of paverage of pKKa2a2 and p and pKKa3a3..

Page 33: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

ArginineArginine

ppKKa1a1 = = 2.172.17

ppKKa2a2 == 9.049.04

ppKKa3a3 == 12.4812.48

ppI I == 10.7610.76

HH33NN CC CC

OO

OO––

HH++

CHCH22CHCH22CHCH22NNHCHCNNHH22

++ NNHH22

Page 34: 27.3 Acid-Base Behavior of Amino Acids. Recall While their name implies that amino acids are compounds that contain an —NH 2 group and a —CO 2 H group,

Table 27.3Table 27.3 Amino Acids with Ionizable Side ChainsAmino Acids with Ionizable Side Chains

HistidineHistidine

ppKKa1a1 = = 1.821.82

ppKKa2a2 == 6.006.00

ppKKa3a3 == 9.17 9.17

ppI I == 7.597.59

HH33NN CC CC

OO

OO––

HH++

CHCH22

NHNHNN


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