Amino Acid

Stereochemistry of the a - Amino Acids Stereo form

NH3+ O

H C
a C O-
 a - carbon atom
H  SP3 hybridization
 Tetrahedral
Glycine (gly)  Line – plane of the page
 solid wedges – forward from the page  chiral, or a stereocenter, or
Fischer projection  dashed wedges - behind the page asymmetric carbon
form  stereoisomers exist
NH3+ O
 nonsuperimposable mirror
a images or enantiomers
H C C O-
 D and L enantiomers
 All amino acids except
CH3
glycine can exist in D and L
NH3+ O
forms because in each case the
a carbon is asymmetric.
H Ca C O-

CH
H3C CH3
 NH3+ O
Chemical analysis of naturally occurring proteins shows
H Ca C O- that nearly all of their constituent amino acids have the l
form.
H C OH

CH3

Threonine (Thr)
 Classification of amino acid
Base on structure

Aliphatic amino acids

A. Mono amino mono carboxylic acids:
Simple amino acids: Glycine, Alanine
Branched chain amino acids:
Valine, Leucine, Isoleucine
Hydroxy amino acids:
Serine, Threonine
Sulphur containing amino acids:
Cysteine, Methionine
Amino acids with amide group:
Asparagine, Glutamine

4
Aliphatic amino acids
B. Mono amino dicarboxylic acids:
Aspartic acid, Glutamic acid
C. Di basic mono carboxylic acids:
Lysine, Arginine
D. Aromatic amino acids:
Phenylalanine, Tyrosine
E. Heterocyclic amino acids:
Tryptophan, Histidine
F. Imino acid:
Proline

5
Base on Side chain
Amino acids having nonpolar aliphatic side chains:
These include Glycine, alanine, valine, leucine, and isoleucine.
These groups are hydrophobic (water repellant) and lipophilic. Therefore, the parts of proteins made up of these amino acids will
be hydrophobic in nature.
the more hydrophobic amino acids such as isoleucine are usually found within the core of a folded protein molecule, where they
are shielded from water.
Proline, methionine
tyrosine can ionize at high pH:

Amino acids having nonpolar aromatic side chains:

These include phenylalanine, tyrosine, and tryptophan.

Memory Aid for Essential Amino Acids

"Any Help In Learning These Little Molecules Proves Truely Valuable"

This stands for
Arginine, Histidine, Isoleucine, Leucine, Threonine, Lysine, Methionine, Phenylalanine, Tryptophan
and Valine in that order.
6 Arginine and Histidine are semi-essential amino acids; while others are essential
Amino acids with polar side chains:
Serine, cysteine, threonine, asparagine, and glutamine.
they can form multiple H bonds with water molecules and/or other good H bond donors and acceptors.
these five amino acids are most often found on the surfaces of proteins, where they can contact the aqueous environment in
cells or in circulation.
- OH group of serine and the - SH group of cysteine are good nucleophiles and often play key roles in enzyme activity.

the oxidation of two cysteine side chains yields a disulfide

Cysteine - can ionize at moderately high pH:
bond:
Amino acids with positively charge (basic) side chains:
Histidine, lysine, and arginine
The basic amino acids are strongly polar, so they are usually found on the exterior surfaces of proteins, where they can be
hydrated by the surrounding aqueous environment, or in substrate binding clefts of enzymes, where they can interact with polar
groups on the substrate that binds to the enzyme.

Amino acids with negatively charge (acidic) side chains:

Aspartic acid and glutamic acid
hydrophilic and tend to be on the surface of a protein molecule, in contact with the surrounding water or a bound substrate.

Non polar amino acids are typically found in the

Concept interiors of soluble proteins, whereas polar and charged
amino acids are typically found on the surfaces of
protein.
 PROPERTIES OF AMINO ACIDS

Glycine, alanine, valine, serine, tryptophan, histidine and proline are sweet in taste;

leucine is tasteless;

while isoleucine and arginine are bitter.

Sodium glutamate is a flavoring agent.

Aspartame, an artificial sweetener contains aspartic acid and phenyl alanine.

All amino acids have high melting points (more than 200°C).

All amino acids are soluble in water and alcohol (polar solvents); but

insoluble in nonpolar solvents (benzene).

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