Hydride, Hydrogen and Proton

hydride
1s

-

-

Proton

+
-

+
Hydrogen atom
1

+

H
1.008

Proton Is Adsorbed or Desorbed
Proton: abundant and small, affects the charge of a molecule
lone pair electrons High pKa Low

H+

Amino

N H
H

H+
Low pKa High

N H
H O

Carboxylic

C

O H O

C

O

H+

Ampholyte contains both positive and negative groups on its molecule

Acidic environment

Neutral environment

Alkaline environment

pK2 ~ 9

NH2 H+ R-C-H COOH
pK1 ~ 2

NH2 H+ R-C-H COO-

NH2 R-C-H COO-

5.5

+1

0
Isoelectric point

-1

Amino Acids Have Buffering Effect
pH 12

9
NH2 H+

pK2

6
3 0

H-C-R COO★

Isoelectric point =

pI

pK1 + pK2 2

pK1

[OH] →

Buffer pH

Environment pH vs Protein Charge

10 9 8 7
Isoelectric point, pI

6 5 4 3

+

0

-

-

Net Charge of a Protein

pKa of Amino Acid Residues
Residues on amino acids can release or accept protons a -COOH R -COOH His -Imidazole·H+ Cys -SH Tyr -OH a -NH3+ R -NH3+ a -COOR -COO+ H+ pKa = 1.8~2.4 + H+ pKa = 3.9~4.3

His -Imidazole + H+ pKa = 6.0 + H+ pKa = 8.3 Cys -S+ H+ pKa = 10 Tyr -Oa -NH2 R -NH2
+ H+ + H+

pKa = 8.8~11 pKa = 10~12.5

Smaller pKa releases proton easier Only His has the residue with a neutral pKa (imidazole) pKa of a carboxylic or amino groups is lower than pKa of the R residues

Amino acids

-COOH -NH2

-R

pH two pKa

pKa of Amino Acids

Gly Ala Val Leu Ile Ser Thr Met Phe Trp Asn Gln Pro Asp Glu His Cys Tyr Lys Arg

G A V L I S T M F W N Q P D E H C Y K R

2.34 2.34 2.32 2.36 2.36 2.21 2.63 2.28 1.83 2.38 2.02 2.17 1.99 2.09 2.19 1.82 1.71 2.20 2.18 2.17

9.60 9.69 9.62 9.68 9.68 9.15 10.4 9.21 9.13 9.39 8.80 9.13 10.6 9.82 9.67 9.17 10.8 9.11 8.95 9.04

pK2
pI

pK1

pK1 + pK2 2 three pKa

pK3
3.86 4.25 6.0 8.33 10.07 10.53 12.48

? ?
pI ? [OH-]

pK2 pK1

H first HOOC-CH2-C-COOH NH3+

+1
pK1 = 2.1

Aspartic acid
Isoelectric point is the average of the two pKa flanking the zero net-charged form

H second HOOC-CH2-C-COONH3+

0
pK2 = 3.9

2.1 + 3.9 = 3.0 2 Isoelectric point
-2
pK3 pK2 pK1

H -OOC-CH -C-COO2

-1
pK3 = 9.8

NH3+ third

-1 0 +1
[OH]

H -OOC-CH -C-COO2 NH2

-2

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