AMINO

ACIDS Amino Acids and their Amides

They play central roles both as building blocks of Acidic amino acids are polar and negatively
proteins and as intermediates in metabolism. charged at physiological pH
Each amino acid contains carboxylic acid with an Amides are polar uncharged, and not ionizable. All
amino group on the alpha carbon. are very hydrophilic
It is the different R-group side chains on the amino Both have a second carboxyl group
acids that make one amino acid different from
another. Aliphatic Amino Acids
Aliphatic R groups are nonpolar and hydrophobic
Basic Structure: Hydrophobicity increases with increasing number
O of C atoms in hydrocarbon chain
|| Although these amino acids prefer to remain
H2N--CH-C--OH inside protein molecules, Ala and Gly are
| ambivalent, meaning they can be inside or outside
R the protein molecule.
Properties:
In water, amino acid can act as either acids or Aromatic Amino Acids
bases (Amphoteric) Relatively nonpolar
Except Glycine, the alpha carbon is chiral and To different degrees. All aromatic amino acids
therefore capable of optical isomerism absorb ultraviolet light
There are 20 amino acids that are found within Tyr and Trp absorb more than do Phe
proteins that convey a vast array of chemical Trp is responsible for most of the absorbance of
versatility. UV light by proteins
The precise amino acid content, and the sequence Tyr is the only one of the aromatic amino acids
of those amino acids of a specific protein with ionizable side chain
determines the function of a protein. Tyr is one of the three hydroxyl containing amino
The chemical properties of the amino acids of acids
proteins determine the biological activity of the
protein. Basic Amino Acids
Humans can produce the 10 of the 20 amino acids. Polar and positively charges
The others must be supplied in the food. Even though the basic amino aids are almost
Take note: Failure to obtain enough of even 1 of always in contact with the solvent, the side chain
the 10 essential amino acids, those that we cannot of lysine has a marked hydrocarbon character
make, results in degradation of the bodys
proteinsmuscle and so forthto obtain one Cyclic Amino Acid
amino acid that is needed. Proline is the only cyclic amino acid
Take note: Unlike fat and starch, the human body Nonpolar and shares many properties with
does not store excess amino acids for later use aliphatic group.
the amino acids must be in the food every day. Proline is one of the ambivalent amino acid
meaning that it can be inside or outside of a
The 10 amino acids that we can produce are: protein molecule.
1. Alanine 6. Glutamine Due to its unique structure, Pro occurs in proteins
2. Asparagine 7. Glycine frequently in turns or bends, which are often on
3. Aspartic Acid 8. Proline the surface
4. Cysteine 9. Serine
5. Glutamic Acid 10. Tyrosine Hydroxyl Amino Acids
Polar uncharged at physiological pH;
The 10 essential amino acids are: hydrophilic
1. Arginine (required for 6. Methionine The hydroxyl groups of Serine and Threonine
the young, but not for 7. Phenylalanine are so high that they are generally regarded at
adults) 8. Threonine non-ionizable
2. Histidine 9. Tryptophan
3. Isoleucine 10. Valine
4. Leucine
5. Lysine

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 Amino Acid Chemical Physical Descriptions
Properties Properties
Non-essential amino acid
Alanine Aliphatic Non-polar Hydrophobic molecule
A Ambivalent (can be inside or outside of the protein molecule.
Ala Note that alanine is the -keto acid pyruvate, an intermediate of sugar metabolism
Transfer of N from peripheral tissue to the liver
Aids in the metabolism of glucose, a simple CHO that the body uses for energy
Guards against the buildup of toxic substances that are released into the muscle cells when muscle protein is
broken down quickly to meet energy needs
Strengthens the immune system by producing antibodies
Asparagine Acidic Polar Amide of Aspartic acid. Amide group does not carry a formal charge under any biologically relevant pH conditions
N (uncharged) The amide is rather easily hydrolyzed, converting Asn to Asp which is thought to be one of the factors related to
Asn the molecular basis of aging.
Has a high propensity to H bond, since the amide group can accept two and donate two H bonds. It is found on the
surface as well as buried within proteins
Common site for attachment of CHO and glycoproteins
Cysteine Sulfur Polar Differs from Ser in a single atomthe Sulfur of the thiol replaces the oxygen of the alcohol
C containing (uncharged) Stabilize extracellular proteins
Cys Can react with itself to form an oxidized dimer by formation of a disulfide bond.
The environment within a cell is too strongly reducing for disulfides to form, but in the extracellular environment,
disulfides can form and play a key role in the stabilizing many such proteins, such as the digestive enzyme of the
small intestine
Aspartic Acid Acidic Polar Act as general acid in enzyme active centers, as well as in maintaining the solubility and ionic character of proteins
D (charged) Proteins in the serum are critical to maintaining the pH balance in the body; it is largely the charged amino acids
Asp that are involved in the buffering properties of proteins. Aspartic acid is alanine with one of the hydrogens
replaced by a carboxylic acid group. The pKa of the carboxyl group of Asp in a polypeptide is about 4.0.
Increases stamina and good for chronic fatigue and depression
Rejuvenates cellular activity, cell formation and metabolism
Helps facilitate the movement of certain minerals across the intestinal lining and into the blood and cells
Aids the function of RNA and DNA which are carriers of genetic information
Glutamic Acid Acidic Polar Has one additional methylene group in its side chain than does aspartic acid. The side chain of carboxyl of Asp s
E (charged) referred to as the carboxyl group, while that of Glu is referred to as ! carboxyl group
Glu In some proteins, due to a vitamin K dependent carboxylase, some glutamic acids will be a dicarboxylic acid,
referred to as ! carboxyglutamic acid, that form tight binding sites for calcium ion
Excitatory neurotransmitter for the CNS, the brain and spinal cord
Important in the metabolism of sugar and fats
Aids in the transportation of potassium into the spinal fluid
Acts as fuel for the brain and helps correct personality disorders
Used in the treatment of epilepsy and mental retardation, muscular dystrophy, and ulcers

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 Glutamine Neutral Polar Amide of Glu, is uncharged under all biological conditions
Q (uncharged) Additional single methylene group in the side chain relative to Asp allows Gln in the free form or as the N-teminus
Gln of proteins to spontaneously cyclize and deamidate yielding the six-membered ring structure pyrrolidone
carboxylic acid, which is found at the N-terminys of many immunoglobulin peptides. This causes obvious
difficulties with amino acid sequence determination
Most abundant amino acid found in muscles; helps build and maintain muscle tissue; helps prevent muscle
wasting that can accompany prolonged bed rest or diseases such as cancer and aids
Brain fuel that increases brain function and mental activity
Assist in maintaining the proper acid/alkaline balance in the body
Promotes a healthy digestive tract; shortens healing time of ulcers, and alleviates fatigue, depression, and
impotence
Decreases sugar cravings and the desire for alcohol; recently used in the treatment of schizophrenia and senility
Glycine Aliphatic Nonpolar Smallest amino acid
G Ambivalent
Gly In aqueous solution, at or near neutral pH, Gly will exist predominantly as zwitterion
The pI will be centered between the pKas of the two ionizable group, the amino group and the carboxylic acid
group
Estimating the pKa of a functional group, it is important to consider the molecule as a whole. For example, Gly is a
derivative of acetic acid and the pKa of acetic acid is well known. Alternatively, Gly could be considered a
derivative of aminoethane
Retards muscle degeneration
Improves glycogen storage, thus freeing up glucose for energy needs
Useful for repairing damaged tissue and promotes healing
Promotes healthy prostate, CNS, and immune system
Proline Cyclic Nonpolar Not an amino acid but an imino acid
P The only cyclic amino acid
Pro Improves skin texture by aiding the production of collagen and reducing the loss of collagen through aging process
Helps in the healing of cartilage and the strengthening of joints, tendons, and heart muscles, works with Vit C to
promote healthy connective tissue
Serine Non- Polar Differs from Ala in that one of the methylenic hydrogens is replaced by a hydroxyl group
S aromatic (uncharged) One of the 2 hydroxy amino acid Both are commonly considered hydrophilic due to the hydrogen bonding capacity
Ser hydroxyl of the hydroxyl group
Needed for the proper metabolism of fats, and fatty acids, the growth of muscle, and maintenance of healthy
immune system
Is a component of myelin sheaths that cover nerve fibers
Important in RNA and DNA function and cell formation; aids in the production of immunoglobulins
Tyrosine Aromatic Nonpolar Important in overall metabolism; is a precursor of adrenaline, norepinephrine, and dopamine which regulate
Y mood and stimulates metabolism and the nervous system
Tyr Aids in the production of melanin (the pigment responsible for hair and skin color) and in the functions of the
adrenal, thyroid, and pituitary glands
Help chronic fatigue, narcolepsy, anxiety, depression, low sex drive, allergies, and headaches
At as mood elevator, suppresses the appetite, and helps reduce body fat

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 Essential Amino acid
Arginine Basic Polar Has a positively charged guanidine group.
R (positively Well designed to bind with phosphate anion, and is often found in the active centers of proteins that bind
Arg charged) phosphorylated substrates
Cation- plays a role in maintaining overall charge balance of a protein (together with Lys)
Plays a role in Nitrogen metabolism
Natural Viagra by increasing blood flow to the penis
Retards the growth of tumors and cancer by enhancing the immune system
Increases the size and activity of the thymus gland, which manufactures T cells, crucial component of the immune
system
Aids in liver detoxification by neutralizing ammonia
Reduces effect of chronic alcohol toxicity
Used in treating sterility in men by increasing sperm count
Aids in weight loss because it facilitates an increase in muscle mass and a reduction of body fat
Assists the release of growth hormones, which is crucial for optimal muscle growth and tissue repair
Major component of collagen which is good for arthritis and connective tissue disorders
Aids in stimulating the pancreas to release insulin
Histidine Basic Polar Has a positively charged imidazole functional group
H (positively The imidazole makes it a common participant in enzyme catalyzed reactions. The unprotonated imidazole is
His charged) nucleophilic and can serve as a general base, while the protonated form can serve as a general acid. The residue
can also serve a role in stabilizing the folded structures of proteins
Found abundantly in hemoglobin
Has been used in the treatment of rheumatoid arthritis, allergies, ulcers, and anemia
For growth ad repair of tissues
Important in maintenance of myelin sheaths, which protect nerve cells
Is needed for the production of red and WBC
Protect the body from radiation damage
Lowers BP, aids I the removal of heavy metals form the body
Aids in sexual arousal
Isoleucine Aliphatic Nonpolar One of the three amino acid having branched hydrocarbon side chains. It is usually interchangeable with Leu and
I occasionally with Val in proteins
Ile The side chains of these amino acid are not reactive and therefore not involved in any covalent chemistry in
enzyme active centers
However, these residues are critically important for ligand binding to proteins, and play central roles in protein
stability. Note also that the carbon of Ile is optically active, just as the of Thr. These 2 amino acid have in
common the fact that they have two chiral centers
Needed for Hb formation
Stabilizes and regulates blood sugar and energy levels
Valuable to athletes because it aids in the healing and repair of muscle tissue, skin, and bones
Has been found to be deficient in people suffering from mental and physical disorders

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 Leucine Aliphatic Nonpolar One of the 3 amino acid with a branched hydrocarbon side chain. It has one additional methylene group in its side
L chain compared with Val
Leu Hydrophobic and buried in folded proteins
Lowers blood sugar levels
Aids in increasing growth hormone production
Works with Ile to promote healing of muscle tissue, skin, and bones
Recommended for those recovering from surgery
Lysine Basic Polar Has a positively charged - amino group (a primary amine)
K (positively Basically Ala with a propylamine substituent on the carbon. The -amino group has a significantly higher pKa
Lys charged) (about 10.5 in polypeptides) than does the - amino group
The amino group is highly reactive and often participates at the active centers of enzymes
Lysines are often found buried with only the -amino group exposed to solvent (hydrophobic character)
Ensure adequate Ca absorption and maintains a proper N balance in adults
Helps form collagen (which makes up cartilage and connective tissue)
Aids in the production of antibodies which have the ability to fight cold sores and herpes outbreaks
Lowers high serum triglyceride levels
Methionine Sulfur Nonpolar Side chain is hydrophobic found buried within proteins
M containing Highly nucleophilic, although it will react with some electrophilic centers
Met It is thought thought the oxidation of the sulfur in a specific methionine of the elastase inhibitor in human lung
tissue by agents in cigarette smoke is one of the causes of smoking-induced emphysema
Met as the free amino acid plays several important roles in metabolism. It can react to form S-Adenosyl-L-
Methionine (SAM) which serves as a methyl donor in reactions
Powerful antioxidant; source of sulfur which prevents disorders of the hair, skin, and nails
Assists in the breakdown of fats, thus helping to prevent a buildup of fat in the liver and arteries, that might
obstruct blood flow to the brain, heart, and kidneys
Helps detoxify harmful agents such as lead and other heavy metals; helps diminish muscle weakness
Prevents brittle hair; protect against the effects of radiation
Beneficial for women who take oral contraceptives because it promotes excretion of estrogen
Reduces the level of His in the body which can cause the brain to relay wrong messages
Phenylalanine Aromatic Nonpolar Derivative of Alanine with phenyl substituent on the carbon.
F Hydrophobic and is free amino acid not very soluble in water
Phe Buried within the protein
The electrons of the phenyl ring can stack with other aromatic systems and often do within folded proteins,
adding to the stability of the structure
Used by the brain to produce norepinephrine, a chemical that transmits signals within nerve cells
Promotes alertness and vitality; elevates mood; decreases pain; aids in memory and learning
Used to treat arthritis, depression, menstrual cramps, migraines, obesity, Parkinsons disease, and schizophrenia
Threonine Non- Polar Both and carbons f Thr are optically active
T aromatic (uncharged) Helps maintain proper protein balance in the body
Thr hydroxyl Important for the formation of collagen, elastin and tooth enamel
Assist metabolism and assimilation
Aids in liver lipoprotic function combined with Asp and Met; prevents the buildup of fat in the liver

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 Tryptophan Aromatic Nonpolar Largest amino acid
W Derivative of Ala, having an indole substituent on the carbon
Trp Indole functional group absorbs strongly in the near UV part of the spectrum. Indole N can H bond, and as a result,
the W, or at least the N is often in contact with solvent in folded proteins
Natural relaxant, alleviates insomnia by inducing normal sleep
Reduces anxiety and depression and stabilizes mood
Enhance the release of growth hormones
Helps in treatment of migraine headaches; helps the immune system function properly
Aids in weight control by reducing appetite
Helps control hyperactivity in children
Valine Aliphatic Nonpolar Needed for muscle metabolism and coordination, tissue repair, and for the maintenance of proper nitrogen
V balance in the body
Val Used as an energy source by muscle tissue; helpful in treating liver and gallbladder disease and promotes mental
vigor and calm emotions.