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Amino Acid pKa Values and Side Chain Identities

Amino Acid Alanine Arginine Asparagine Aspartic Acid Cysteine Glutamic Acid Glutamine Glycine Histidine Isoleucine Leucine Lysine Methionine Phenylalanine Proline Serine Threonine Tryptophan pKa Values -CO2H -NH3+ 2.34 9.69 2.17 9.04 2.02 2.09 1.71 2.19 2.17 2.34 1.82 2.36 2.36 2.18 2.28 1.83 1.99 2.21 2.63 2.38 8.84 9.82 10.78 9.67 9.13 9.60 9.17 9.68 9.60 8.95 9.21 9.13 10.60

N

Side 12.48

Side Chain (Z) ­ "fully" protonated

­CH3 NH2

H2 NCNHCH2CH2 CH2­ O

3.86 8.33 4.25

H2 NCCH2 ­ ­CH2CO2H ­CH2SH ­CH2CH2CO2H O H2 NCCH2CH2 ­ ­H

6.04

HN

CH2­ NH

10.79

­CH(CH3)CH2CH3 ­CH2CH(CH3)2 ­CH2CH2CH2CH2NH3+ ­CH2CH2SCH3

CH2­

black = side chain

CO2­

9.15 9.10 9.39

H ­CH2OH ­CH(OH)CH3

H

CH2­

Tyrosine Valine

2.20 2.32

9.11 9.62

10.07

N H

HO CH2­

­CH(CH3)2

-

CO2 General L-amino acid structure at physiological pH H3N Z

H

Dr. Kline ­ Santa Monica College - 2006

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