Properties of Amino Acids

This table gives selected properties of some important amino Chemical Substances” in Section 5 of this Handbook. Absorption
acids and closely related compounds. The first part of the table spectra and optical rotation data can be found in Reference 3.
lists the 20 “standard” amino acids that are the basic constituents Partial molar volume is taken from Reference 5; other thermody-
of proteins. The second part includes other amino acids and re- namic properties, including solubility as a function of tempera-
lated compounds of biochemical importance. Within each part of ture, are given in References 3 and 5. Most of the pK values come
the table the compounds are listed by name in alphabetical order. from References 1, 6, and 7.
Structures are given in the following table.

Symbol: Three-letter symbol for the standard amino acids References

Mr : Molecular weight 1. Dawson, R. M. C., Elliott, D. C., Elliott, W. H., and Jones, K. M., Data
tm: Melting point for Biochemical Research, Third Edition, Clarendon Press, Oxford,
pKa , pKb , pKc , pKd: Negative of the logarithm of the acid dis- 1986.
sociation constants for the COOH and NH2 groups 2. O’Neil, Maryadele J., Ed., The Merck Index, Fourteenth Edition, Merck
(and, in some cases, other groups) in the molecule & Co., Rahway, NJ, 2006.
(at 25 °C) 3. Sober, H. A., Ed., CRC Handbook of Biochemistry. Selected Data for
pI: pH at the isoelectric point Molecular Biology, CRC Press, Boca Raton, FL, 1968.
4. Voet, D., and Voet, J. G., Biochemistry, Second Edition, John Wiley &
S: Solubility in water in units of grams of compound per
Sons, New York, 1995.
kilogram of water; a temperature of 25 °C is under- 5. Hinz, H. J., Ed., Thermodynamic Data for Biochemistry and
stood unless otherwise stated in a superscript. When Biotechnology, Springer-Verlag, Heidelberg, 1986.
quantitative data are not available, the notations sl.s. 6. Fasman, G. D., Ed. Practical Handbook of Biochemistry and Molecular
(for slightly soluble), s. (for soluble), and v.s. (for very Biology, CRC Press, Boca Raton, FL, 1989.
soluble) are used. 7. Smith, R. M., and Martell, A. E., NIST Standard Reference Database
V20: Partial molar volume in aqueous solution at infinite 46: Critically Selected Stability Constants of Metal Complexes
dilution (at 25 °C) Database, Version 3.0, National Institute of Standards and Technology,
Gaithersburg, MD, 1997.
Data on the enthalpy of formation of many of these compounds 8. Ramasami, P., J. Chem. Eng. Data, 47, 1164, 2002.
are included in the table “Standard Thermodynamic Properties of
V20/
Symbol Name Mol. form. Mr tm/°C pKa pKb pKc pKd pI S/g kg-1 cm3 mol-1
Ala l-Alanine C3H7NO2 89.09 297 2.33 9.71 6.00 166.9 60.54
Arg l-Arginine C6H14N4O2 174.20 244 2.03 9.00 12.10 10.76 182.6 127.42
Asn l-Asparagine C4H8N2O3 132.12 235 2.16 8.73 5.41 25.1 78.0
Asp l-Aspartic acid C4H7NO4 133.10 270 1.95 9.66 3.71 2.77 5.04 74.8
Cys l-Cysteine C3H7NO2S 121.16 240 1.91 10.28 8.14 5.07 v.s. 73.45
Gln l-Glutamine C5H10N2O3 146.14 185 2.18 9.00 5.65 42
Glu l-Glutamic acid C5H9NO4 147.13 160 2.16 9.58 4.15 3.22 8.6 89.85
Gly Glycine C2H5NO2 75.07 290 2.34 9.58 5.97 239 43.26
His l-Histidine C6H9N3O2 155.15 287 1.70 9.09 6.04 7.59 43.5 98.3
Ile l-Isoleucine C6H13NO2 131.17 284 2.26 9.60 6.02 34.2 105.80
Leu l-Leucine C6H13NO2 131.17 293 2.32 9.58 5.98 23.8 107.77
Lys l-Lysine C6H14N2O2 146.19 224 2.15 9.16 10.67 9.74 5.8 108.5
Met l-Methionine C5H11NO2S 149.21 281 2.16 9.08 5.74 56 105.57
Phe l-Phenylalanine C9H11NO2 165.19 283 2.18 9.09 5.48 27.9 121.5
Pro l-Proline C5H9NO2 115.13 221 1.95 10.47 6.30 1625 82.76
Ser l-Serine C3H7NO3 105.09 228 2.13 9.05 5.68 250 60.62
Thr l-Threonine C4H9NO3 119.12 256 2.20 8.96 5.60 90.6 76.90
Trp l-Tryptophan C11H12N2O2 204.23 289 2.38 9.34 5.89 13.2 143.8
Tyr l-Tyrosine C9H11NO3 181.19 343 2.24 9.04 10.10 5.66 0.51
Val l-Valine C5H11NO2 117.15 315 2.27 9.52 5.96 88 90.75

V20/
Name Mol. form. Mr tm/°C pKa pKb pKc pKd pI S/g kg-1 cm3 mol-1
N-Acetylglutamic acid C7H11NO5 189.17 199 s.
N6-Acetyl-l-lysine C8H16N2O3 188.22 265 2.12 9.51
β-Alanine C3H7NO2 89.09 200 3.51 10.08 890 58.28
2-Aminoadipic acid C6H11NO4 161.16 207 2.14 4.21 9.77 3.18 2.240
dl-2-Aminobutanoic acid C4H9NO2 103.12 304 2.30 9.63 6.06 210 75.6
dl-3-Aminobutanoic acid C4H9NO2 103.12 194.3 3.43 10.05 7.30 1250 76.3
4-Aminobutanoic acid C4H9NO2 103.12 203 4.02 10.35 971 73.2
10-Aminodecanoic acid C10H21NO2 187.28 188.5 167.3

7-1
7-2 Properties of Amino Acids

V20/
Name Mol. form. Mr tm/°C pKa pKb pKc pKd pI S/g kg-1 cm3 mol-1
7-Aminoheptanoic acid C7H15NO2 145.20 195 v.s. 120.0
6-Aminohexanoic acid C6H13NO2 131.17 205 7.29 850 104.2
l-3-Amino-2- C4H9NO2 103.12 185 s.
methylpropanoic acid
2-Amino-2-methylpropanoic C4H9NO2 103.12 335 2.36 10.21 5.72 137 77.55
acid
9-Aminononanoic acid C9H19NO2 173.26 191 151.3
8-Aminooctanoic acid C8H17NO2 159.23 192 136.1
5-Amino-4-oxopentanoic C5H9NO3 131.13 118 4.05 8.90
acid
5-Aminopentanoic acid C5H11NO2 117.15 157 dec s. 87.6
o-Anthranilic acid C7H7NO2 137.14 146 2.05 4.95 3.514
Azaserine C5H7N3O4 173.13 150 8.55 v.s.
Canavanine C5H12N4O3 176.17 172 2.50 6.60 9.25 7.93 v.s.
l-γ-Carboxyglutamic acid C6H9NO6 191.14 167 1.70 9.90 4.75 3.20
Carnosine C9H14N4O3 226.23 260 2.51 9.35 6.76 322
Citrulline C6H13N3O3 175.19 222 2.32 9.30 5.92 s.
Creatine C4H9N3O2 131.13 303 2.63 14.30 16
l-Cysteic acid C3H7NO5S 169.16 260 1.89 8.70 1.30 v.s.
l-Cystine C6H12N2O4S2 240.30 260 1.50 8.80 2.05 8.03 0.17
2,4-Diaminobutanoic acid C4H10N2O2 118.13 118.1 1.85 8.24 10.44 9.27 s.
3,5-Dibromo-l-tyrosine C9H9Br2NO3 338.98 245 2.72
3,5-Dichloro-l-tyrosine C9H9Cl2NO3 250.08 247 1.97
3,5-Diiodo-l-tyrosine C9H9I2NO3 432.98 213 2.12 9.10 6.16 0.62
Dopamine C8H11NO2 153.18 10.36 8.88 s.
l-Ethionine C6H13NO2S 163.24 273 2.18 9.05 13.10
N-Glycylglycine C4H8N2O3 132.12 263 3.13 8.10 231
Guanidinoacetic acid C3H7N3O2 117.11 282 2.82 5
Histamine C5H9N3 111.15 83 9.83 6.11 v.s.
l-Homocysteine C4H9NO2S 135.19 232 2.15 8.57 10.38 5.55 s.
Homocystine C8H16N2O4S2 268.35 264 1.59 9.44 2.54 8.52 0.2
l-Homoserine C4H9NO3 119.12 203 2.27 9.28 6.17 1100
3-Hydroxy-dl-glutamic acid C5H9NO5 163.13 209 3.28
5-Hydroxylysine C6H14N2O3 162.19 2.13 8.85 9.83 9.15
trans-4-Hydroxy-l-proline C5H9NO3 131.13 274 1.82 9.47 5.74 361 84.49
l-3-Iodotyrosine C9H10INO3 307.08 205 2.20 9.10 8.70 sl.s.
l-Kynurenine C10H12N2O3 208.21 194 sl.s.
l-Lanthionine C6H12N2O4S 208.24 294 1.5
Levodopa C9H11NO4 197.19 277 2.32 8.72 9.96 11.79 1.6520
l-1-Methylhistidine C7H11N3O2 169.18 249 1.69 8.85 6.48 200
l-Norleucine C6H13NO2 131.17 301 2.31 9.68 6.09 15 107.7
l-Norvaline C5H11NO2 117.15 307 2.31 9.65 107 91.8
l-Ornithine C5H12N2O2 132.16 140 1.94 8.78 10.52 9.73 v.s.
O-Phosphoserine C3H8NO6P 185.07 166 2.14 9.80 5.70
l-Pyroglutamic acid C5H7NO3 129.12 162 3.32
Sarcosine C3H7NO2 89.09 212 2.18 9.97 428
Taurine C2H7NO3S 125.15 328 -0.3 9.06 105
l-Thyroxine C15H11I4NO4 776.87 235 2.20 10.01 6.45 sl.s.