Amphoteric amino acids

Rosenblatt, W., Amino acid amphoterics, in Amphoteric Surfactants, 2nd Edn, Lomax E. G. (Ed.), Surfactant Science Series 59, Marcel Dekker, New York (1996), pp. 49-73. 

The hide proteins differ in amino acid composition and physical stmcture. The principal amino acids (qv) of the hide proteins are hsted in Table 1. Of particular importance is the difference in the water solubiUty of the proteins. AH of the proteins are soluble in water when heated, and upon the addition of either strong acids or bases. Proteins (qv) are amphoteric, possessing both acid and base binding capacity. 

Wool has a complex chemical stmcture, composed mainly of a large number of different proteins (87). It is amphoteric in character because of the presence of basic amino and acidic carboxyl groups in the side chains of some of the component amino acids. In an aqueous acidic dyebath, protonation of the amino and carboxyl groups results in a net positive charge on the fiber. 

It is interesting to note that the amino acid side chains may be either neutral as in valine, acidic as in glutamic acid or basic as in lysine. The presence of both acidic and basic side chains leads to proteins such as casein acting as amphoteric electrolytes and their physical behaviour will depend on the pH of the environment in which the molecules exist. This is indicated by Figure 30.2, showing a simplified protein molecule with just one acidic and one basic side group. 

Solutions of polyelectrolytes contain polyions and the free (individual) counterions. The dissociation of a polyacid or its salt yields polyanions, and that of a polybase or its salt yields polycations, in addition to the simple counterions. The polyampholytes are amphoteric their dissociation yields polyions that have anionic and cationic functions in the same ion and often are called zwitterions (as in the case of amino acids having HjN and COO groups in the same molecule). Such an amphoter will behave as a base toward a stronger acid and as an acid toward a stronger base its solution properties (particularly its effective charge) will be pH dependent, and an isoelectric point (pH value) exists where anionic and cationic dissociation is balanced so that the polyion s charges add up to zero net charge (and solubility is minimal). 

In the two equations above, notice that water is acting as an acid in one instance and as a base in the other. Substances like water that can act as an acid or a base depending on the circumstances are called amphoteric substances. The word comes from the Greek prefix ampho-, which means both. Water is the most common amphoteric substance, but amino acids, proteins, and some metal oxides—such as aluminum oxide (Al203) and zinc oxide (ZnO), for example—can also act as amphoteric substances. 

Some amphoteric softeners such as amino acids (10.237) and sulphobetaines (10.238) are more effective and durable than the nonionic types but less durable than the cationics moreover, they tend to be expensive. Other amphoteric types include the zwitterionic forms of quaternised imidazolines (10.239) long-chain amine oxides (10.240) also exhibit softening properties. 

Amphoteric. Compounds having the capability of acting as an acid or a base. Amino acids are amphoteric—their molecules contain both an acid group (-COOH) and a basic group (-NH2). 

H+X and Y+OH must be stable species in solution. Amphoteric species such as amino acids are retained on the suppressor column and, therefore. 

Referring to chemical species possessing the ability to exhibit either acidic or basic properties (e.g., amino acids). This property actually depends on the medium. Eor example, sulfuric acid is an acid, when studied in water however, it becomes amphoteric when studied in superacids. 

When proteins undergo hydrolysis, you wind up with 22 a amino acids, 20 of which are regulcir amino acids and 2 of which are derived amino acids. Amino acids are amphoteric (they possess the characteristics of both acids and bases and can react as either) because both acidic and basic groups are present. An internal acid-base reaction produces a dipolar ion known as a zwitterion (you can see the general structure of one in Figure 16-33). 

Since peptides are amphoteric, Zt and Zc are expected to show nonlinear dependencies on pH. Similar behavior has been observed for various synthetic peptides separated on both strong anion and strong cation HP-IEX sorbents. As a consequence, the minima in the In /t iex i versus pH plots at a defined concentration of displacing salt will not usually occur at the predicted p/ value of the peptide, but rather at another pH value. Implementation of an optimized HP-IEX separation of peptides thus requires that the sequence microlocality and extent of ionization of the surface-accessible amino acid side chains, or the N- and C-terminal amino and carboxy groups, respectively, are taken into account. 

CHEMICAL PROPERTIES OF AMINO ACIDS ACID-BASE (AMPHOTERIC) PROPERTIES... 

Isoelectric point (pi) or isoelectric pH is the pH at which a molecule carries no net electrical charge, i.e. zero charge. It is an important measure of the acidity or basicity of an amino acid. To have a sharp isoelectric point, a molecule must be amphoteric, i.e. it must have both acidic and basic functional groups, as found in amino acids. For an amino acid with only... 

Amphoteric Substance. A substance having both acid and basic props, such as amino-acids, A1 hydroxide, etc Ref Hackh(1944),50... 

Substances having this dual nature are amphoteric and are often called ampholytes (from amphoteric electrolytes ). A simple monoamino monocarboxylic a-amino acid, such as alanine, is a diprotic acid when fully protonated—it has two groups, the —COOH group and the —NHj group, that can yield protons ... 

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