The high melting point of glycine and other amino acids is more consistent with this zwitterionic structure than the neutral form that is often drawn. These “internal salts” are known as zwitterions. Note that, as drawn, the molecule bears no net charge since the positive and negative charges balance out. Glycine has become a salt, with a negatively charged carboxylate group and a positively charged ammonium group. The pK a of the carboxylic acid is 2.24 and the pK a of the amino group is 9.60. Here’s what it would look like for the simplest amino acid, glycine. When dissolved in water ( especially when dissolved in the polar solvent water!) we should likewise expect an acid-base reaction between the carboxylic acid and the amine. The term amphoteric is often used to describe amino acids, meaning that they are capable of acting as both acids and bases. They are also bases containing an amino group. Should amino acids behave any differently than the carboxylic acids and amines we’re familiar with? This is a favorable equilibrium because the reaction proceeds from a stronger acid and a stronger base to a weaker acid and a weaker base. When a carboxylic acid (pH 4) is added to a solution containing an amine (R-NH 2), an acid-base reaction quickly occurs, resulting in formation of the ammonium salt R-NH 3(+) with a pK a of about 9. We often like to draw them like this:Īlthough simple, these drawings don’t accurately convey the physical properties of these molecules, especially under physiological conditions. (Advanced) References and Further ReadingĪmino acids contain a carboxylic acid and an amino group.pI Calculations for Amino Acids With Basic Side Chains.pI Calculations for Amino Acids With Acidic Side Chains.Calculating Isoelectric Point pI from pKa Values.The Isoelectric Point, pI, Is the pH At Which Negative and Positive Charges are Balanced.For amino acids with basic sidechains, the pI can be calculated by averaging the pK a values of the least acidic groups.For amino acids with acidic sidechains, the pI can be calculated by averaging the pK a values of the two most acidic groups. ![]() For amino acids with neutral sidechains, the pI can be calculated by averaging the pK a values of the carboxylic acid and ammonium groups.At this pH, the amino acid will not migrate in an applied electric field. In practice, the charges on an amino acid only balance out to zero at one specific pH value, called the isoelectric point pI.The zwitterionic form has two point charges but has a net charge of 0. ![]()
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