Amino

Acid
GROUP 2
 Importance
of Biomedical
AMINO ACID
 Biomedical- relating to both
biology and medical
They participate in Cellular Functions
Short polymers of amino acids called peptides
perform prominent roles in the
neuroendocrine system as hormones,
hormone-releasing factors, neurotransmitters.
Human diet must contain adequate quantities
of these nutritionally essential amino acids.
 Properties
of Amino Acid
 The Genetic Code Specifies
20 L-a-Amino Acids
All amino acids share the same absolute configuration
as L-glyceraldehyde, however some are dextrorotatory
and some are levorotatory. The free L-O amino acids
ornithine, citrulline, and argininosuccinate all play
significant parts in metabolic processes. Free D-serine
and D-aspartate are naturally occurring D-amino acids
in brain tissue. D-alanine and D-glutamate are naturally
occurring D-amino acids in bacteria and some
antibiotics.
 Only L-a-Amino Acids Occur
in Proteins

With the sole exception of glycine, the £t-carbon of

amino acids is chiral. Although some protein amino
acids are dextrorotatory and some levorotatory, all
share the absolute configuration of L-glyceraldehyde
and thus areL-O-amino acids. Severalfree L-O-amino
acids fulfill important roles in metabolic processes.
 Only L-a-Amino Acids Occur
in Proteins
Examples in- clude ornithine, citrulline, and
argininosuccinate that participate in urea synthesis;
tyrosine in formation of thyroid hormones; and
glutamate in neurotransmitter biosynthesis. D-Amino
acids that occur naturally in- clude free D-serine and D-
aspartate in brain tissue, D-alanine and D-glutamate in
the cell walls of gram- positive bacteria, and D-amino
acids in some nonmam- malian peptides and certain
antibiotics.
 Amino Acid May
Have Positive,
Negative or Zero
Net Charge
AMINO ACID
Amino Acids May Have Positive, Negative, Molecules that
contain an equal number of ioniz or Zero Net Charge

Both charged and uncharged forms of the ionizable —

COOH (carboxyl) and —NH3' (amino) weak acid groups

exist in solution in protonic equilibrium:

Amino Acids May Have Positive, Negative, Molecules that
contain an equal number of ioniz or Zero Net Charge
 Zwitterions
Molecules that contain an equal number of ionizable
groups of opposite charge and that therefore bear no net
charge.

Reactions without protonic equilibria frequently utilize the uncharged

representation B (above). Because the amino group would likewise be
protonated at a pH low enough to protonate the carboxyl group, structure B
cannot exist in aqueous solution.
 pKa Values Express the Strengths
of Weak Acids

Histidine's imidazole group and arginine's guanidino group

are resonance hybrids that have positive charge split
between all three nitrogens. The net charge on an amino
acid is the algebraic total of all the positively and
negatively charged groups present. pH changes the charge
on amino acids and their derivatives by modifying pH.
At Its Isoelectric pH (pl), an Amino Acid Bears No Net
Charge

ex.

The isoelectric pH, commonly known as the pl, is the pH

midway between pl c values on each side of the iso-
nelectric species, and is the pH for an amino acid such as
alanine that has only two dissociating groups.
 At Its Isoelectric pH (pl), an Amino Acid Bears No Net
Charge

For polyfunctional acids, pI is also the pH midway be-

tween the pKa values on either side of the isoionic species.
For example, the pI for aspartic acid is
At Its Isoelectric pH (pl), an Amino Acid Bears No Net
Charge

Electrophoresis at pH 7.0 will separate C — NH2IIO+ NH2 C

== NH2INH2, and so will separate two molecules with pI
values of 6.0 and 8.0. Similar considerations apply to
under- Figure J—2. standing chromatographic separations
on ionic sup- ports such as DEAE cellulose.
 pKa Values Vary With the Environment

A functional group's pKa will depend on where it is located

within a certain protein. Thus, a nonpolar environment
increases a carboxyl group's Ka, making it a weaker acid,
while decreasing an amino group's Ka (a stronger acid).
 The Solubility and
Melting Points of
Amino Acids Reflect
Their Ionic
Character
 The Solubility and Melting Points of Amino Acids
Reflect their Ionic Character

Since multiple charged groups are present on amino acids,

they are readily solvated by, and hence soluble in, polar
solvents such as water and ethanol, but insoluble in
nonpolar solvents such as benzene, hexane, and ether.
Their high melting points (>200°C) reflect the high energy
needed to disrupt the ionic forces that stabilize the crystal
lattice.