Amino acids
There
are more than 300 amino acids found in nature. However, only 20 of them are
present in proteins. Each amino acid has three distinct groups
a. A primary amino group (Except for the amino acid
proline, which has a secondary amino or imino group)
b. A carboxylic acid group and
c. A distinct side chain or R group.
The
chemical nature of the side chain in each amino acid determines the property of
that amino acid and the role it plays in a protein structure. Considering this
important role of the side chain, amino acids are classified into different
groups based on their side chain.
These
amino acids have non polar groups as their side chains and are shown in Table
3.1. These non polar side chains are similar to lipids and tend to clump
together in an aqueous environment by means of a special type of interaction
called hydrophobic interaction. Hence, these amino acids are also called
hydrophobic amino acids. These side chain groups (are less likely to lose or
gain protons) form hydrogen bond or ionic bonds.
The
amino acids serine, threonine, tyrosine, cysteine, asparagine and glutamine
have a net zero charge at neutral pH. However at alkaline pH the side chain of
cysteine and tyrosine can lose a proton. The polar hydroxyl group (-OH) present
in the side chains of serine, threonine and tyrosine can form a hydrogen bond.
Similarly, the cysteine side chain can form disulphide bonds. The details of
hydrogen bond and disulphide bonds along with their role in protein structure
and stability will be explained in a later section of this unit.
At
physiologic pH the amino acids arginine and lysine are positively charged due
to the ionization of their side chains. The side chain of the amino acid
histidine acts as a weak base and in proteins histidine is either neutral or
basic depending on the chemical environment.
All amino acids except glycine have
at least one asymmetric carbon atom and hence they exist as stereo isomers and
are normally represented as D and L isomers. Proteins are always made up of L
amino acids. However D amino acids can be found in antibiotics, bacterial cell
walls etc.
Amino
acids have both carboxylic acid and amino groups. Similarly, the side chains of
acidic and basic amino acids contain additional ionisable groups. Recall that
acids are proton donors, where as bases are proton acceptors and the
quantitative relationship between pH of a solution and the concentration of the
weak acid and its conjugate base is given by Henderson-Hasselbalch equation.
The
dissociation of the acidic and basic groups can be explained with alanine as an
example. The three different ionic forms of alanine in acidic, neutral and
basic solutions is explained in Figure 3.4
Note
that at acidic pH both the amino and carboxylic acid groups are protonated
(Form and as the pH increases the –COOH group dissociates to become Form II. At
basic pH the -NH3+ group can dissociate to become Form
III.
The conversion among the three
different forms is heavily influenced by pH. In acidic solution the amino acid
behaves like a protonated derivative and moves towards cathode under an
electric field. In an alkaline medium the same amino acid behaves like an anion
and moves towards anode.
At a particular pH, the net charge of
an amino acid becomes neutral (Form II) and such ionic forms are known as
zwitter ions and the corresponding pH is known as its iso electric point (pI).
The titration curve of alanine is given in figure 3.5 Note that since there are
two ionisable groups in alanine, it has two pKa values denoted as pKa1which
is equal to 2.3 and pKa2 which is equal to 9.1. The iso electric
point is denoted as pI and for alanine it is 5.7.
Ninhydrin
oxidatively decarboxylates an amino acid to CO2 and an aldehyde. The
reduced ninhydrin subsequently reacts with another molecule of ninhydrin to
form a purple complex which absorbs light at 570 nm
Certain
amino acids cannot be synthesised by our body. Such amino acids must be
compulsorily included in our diet for a healthy life. Such amino acids are
called essential amino acids. For humans 10 amino acids are essential, that
includes arginine, methionine, histidine, phenylalanine, valine,leucine, isoleucine,
lysine, threonine and tryptophan (MATT VILL PHLY).
Related Topics
Privacy Policy, Terms and Conditions, DMCA Policy and Compliant
Copyright © 2018-2024 BrainKart.com; All Rights Reserved. Developed by Therithal info, Chennai.