1.

Know and identify the major types of functional groups found in biochemical
compounds of the human body
Major types of functional groups found in biochemical compounds of the human
body
Bonds usually shared between: Carbon Oxygen , Carbon Nitrogen, Carbon
Sulfur, Carbon Phosphate
Carbon Carbon Bond & Carbon Hydrogen Bonds: Electrons shared equally,
Nonpolar, and relatively unreactive
Carbon Oxygen & Carbon Nitrogen bonds: Electrons shared unequally, polar
bonds, and reactive
o Carbon-oxygen groups (6): Alcohol, Aldehyde, Ketone, Carboxylic Acid, Ether,
Acid Anhydride

o Carbon-sulfur groups (2): Sulfhydryl and

(Disulfide in Proteins and INSULIN)

Disulfide

o Carbon-Nitrogen Groups (2): Amino Groups

(Primary, Secondary, Tertiary) and Quaternary Amine
Amino groups carry positive charges
Choline = Quaternary Amine
Dopamine (primary) plays important roles in the
brains (as a neurotransmitter) and as a chemical messenger in locations like the
blood vessels, the kidneys, the pancreas, the digestive system & the immune system.
o Esters (Thioester) and Amides (Phosphoester) Amide has a C=O attached

2. Explain how the formation of esters, thioesters, amides, phosphoesters and

anhydrides occur and be able to identify each group
Partial charges on carbon-oxygen, carbon-nitrogen, and carbon-sulfur bonds.
Ester: Formed by reacting an Acid and Alcohol Loss of H20

Thioester: Formed by reacting an Acid and Sulfhydryl Loss of H20

Phosphoesters: Formed by reacting a

Phosphoric Acid and Alcohol Loss of H20

Amide: Formed by reacting Acid and Amine

Loss of H20

Anhydrides: Formed by reacting Acid and Acid Loss of H20

3. Know how to name different biochemical compounds

Know Nomenclature: The alpha carbon refers to the first carbon that attaches
to a functional group (the carbon is attached at the first or alpha position).
Therefore, the second carbon is the beta carbon, and so on and so forth.
Gamma Hydroxybutyrate

Two systems for identifying the carbon atoms in a compound. This compound is called 3hydroxybutyrate or -hydroxybutyrate.

-hydroxybutyric acid: is produced in mammalian tissues (mainly the liver). Found in

urine of patients suffering from lactic acidosis and ketoacidosis. Generally appears in
situations related to deficient energy metabolism caused by a pyruvate dehydrogenase
deficiency.
-hydroxybutyric acid: is synthesized in the liver from acetyl-CoA . It can be used as an
energy source by the brain when blood glucose is low. Diabetic & alcoholic ketoacidosis
results in an increase -hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle
stalling and shifting of glucose towards ketone body production.
-hydroxybutyric acid: is a naturally occurring substance found in the human central
nervous system. Medically used as a general anesthetic. GHB is a central nervous system
depressant used as an intoxicant.
Chemical structure of Ketone Bodies (ketones smell sweet)
o The ketone bodies -hydroxybutyrate, acetoacetate, and acetone. -hydroxybutyrate
and acetoacetateare are formed in the liver. Acetone (CH3-CO-CH3) is produced by
nonenzymatic decarboxylation of acetoacetate. However, acetone is expired in the
breath and not metabolized to a significant extent in the body, whereas -

hydroxybutyrate and acetoacetate are used by muscles and the nervous system as an
energy source.

4. Identify different classes of carbohydrates and their derivatives, plus be able to

state their functions.
CARBOHYDRATES (Oxidized to CO2 and H2O (4kcal/g) (know)
Monosaccharide Fructose (ketohexose), glucose (D-Glucose) and Mannose (DMannose)
o Triose(2), Tetrose(3), Pentose(5), Hexose(6), and Heptose(7)
Length of sugar Chains (carbons)
o Aldoses or Ketoses, (CH2O)X (X>=3)
o Can be both D and L sugars
o Most sugars in human tissues are D sugars
o Pyranose {6 membered ring (consisting of 5C atoms
and one oxygen atom)
Glucose, Galactose
o Furanose {5 membered ring (consisting of 4C atoms
and one oxygen atom)
Fructose, Ribose, Deoxyribose sugars
o Oxidized and reduced sugars Just know the definition of this
Reducing sugars Open-chain forms of 5 or 6 carbon sugars that expose the
carbonyl group to react with reducing agents
Oxidized and reduced sugars. The affected group is shown in the colored box.
Gluconic acid (D-gluconate) is formed by oxidation of the glucose aldehyde carbon.
Glucuronic acid is formed by oxidation of the glucose terminal OH group. Sorbitol, a
sugar alcohol, is formed by reduction of the glucose aldehyde group. Deoxyribose is
formed by reduction of ribose.

o D-

sugars are the only

sugars found in the body
Enantiomers: one of two stereoisomers that are mirror images of each other that are
non-superimposable.
D- and L-glyceraldehyde. The carbon in the center contains four different substituent groups
arranged around it in a tetrahedron. A different arrangement creates an isomer that is a nonsuperimposable mirror image. If you rotate the mirror image structure so that groups 1 and 2
align, group 3 will be in the position of group 4, and group 4 will be in position 3. B. Dglyceraldehyde and D-glucose. These sugars have the same configuration at the asymmetric
carbon atom farthest from the carbonyl group. Both belong to the D series. Asymmetric
carbons are shown in red.

o Monosaccharides: Stereoisomers: same chemical formula, different -OH

position
o Examples of stereoisomers. These compounds have the same chemical formula
(C6H12O6) but differ in the positions of the hydroxyl groups on their asymmetric carbons
(in red)

Monosaccharides Derivatives (memorize): KNOW

o Sugar acids
Ascorbic acid (Vitamin C): scurvy
Glucuronic acid: conjugated bilirubin
Bilirubin that has been conjugated (mainly to glucuronic acid) in the liver- direct
result to the van den bergh test. High blood levels indicate obstructive or
hepatocellular origin of the jaundice.
o Deoxy sugars
2-Deoxyribose: DNA
o Sugar alcohols (polyols)
Glycerol, glycerol 3-phosphate
Sorbitol: cataract
Galactitol: cataract
o Amino sugars
Glucosamine and galactosamine
o Sugar esters
Glycosidic bond with phosphate or sulfate
o Glycosylation
Microvascular disease, hyaline arteriolosclerosis
Disaccharide - Sucrose, lactose
o Contains two monosaccharides joined by an O-glycosidic bond
N- and O-glycosidic bonds. Adenosine triphosphate (ATP) contains a , Nglycosidic bond.
Lactose contains an O-glycosidic (14) bond..
o Maltose - glucose + glucose, starch breakdown product
o Lactose - glucose + galactose, milk sugar
o Sucrose - glucose + fructose, table sugar, nonreducing
Polysaccharide Starch
o Oligosaccharides - 3 to 12 monosaccharides, form glycoproteins
o Polysaccharides - Tens to thousands of monosaccharides joined by glycosidic bonds
Starch
Amylose: -1, 4 linkage
Amylopectin: -1, 4 linkage, -1, 6 linkage
Glycogen: more highly branched than amylopectin
Cellulose: -1, 4 linkage
Hyaluronic acid and other glycosaminoglycans - Extracellular matrix

5. Define enantiomers, diastereomers, stereoisomers, mutarotation & oxidized and

reduced sugars. Also know the difference between pyranose and furanose.
Stereoisomers: isomeric molecules that have the same molecular formula & sequence
of bonded atoms, but that differ only in 3-D orientations of their atoms in space
Anomers: one of two stereoisomers of a cyclic carbohydrates that differs only in its
configuration at the anomeric carbon.
Enantiomers: one of two stereoisomers that are mirror images of each other that are
non-superimposable
Diastereomers: stereoisomers that are not enantiomers (they are not mirror images of
each other)
Tautomers: are two molecules with the same molecular formula but different
connectivity (constitutional isomers)
Polymers: a large molecule composed of many repeated subunits (also known as
monomers)
Mutarotation is the interconversion of - and - anomers (isomers at the anomeric
center). Anomeric center is the site at which ring opening occurs.
6. Identify each class of lipids, list their functions and explain their relationships
with specific diseases
Lipids
Fatty acids
o Greatest energy source of energy for cells - Except brain cells and RBC
o Two essential FA: -linolenic acid & linoleic acid
o Composed of an unbranched hydrocarbon chain with a terminal carboxyl group
o Short vs. long chain, Saturated vs. unsaturated, Cis vs. trans double bond,
o Carnitine deficiency - Carnitine shuttle long chain FA from the cytosol into the
mitochondria
o Nonketotic hypoglycemia
o Saturated fatty acids and unsaturated fatty
acids. In stearic acid, the saturated fatty acid at
the top of the figure, all the atoms are shown. A
more common way of depicting the same structure
is shown below. The carbons are either numbered
starting with the carboxyl group or given Greek
letters starting with the carbon next to the
carboxyl group. The methyl (or ) carbon at the
end of the chain is always called the -carbon,
regardless of the chain length. The symbol 18:0
refers to the number of carbon atoms (18) and the
number of double bonds (0). In the unsaturated
fatty acids shown, not all of the carbons are
numbered, but note that the double bonds are cis
and spaced at three-carbon intervals. Both 3 and
6 fatty acids are required in the diet. B. Cis and
trans double bonds in fatty acid side chains. Note that the cis double bond causes the
chain to bend.
o Trans fatty acids - margarine, risk factor for atherosclerosis
o Oxidation of unsaturated fatty acids - membrane damage, hemolytic anemia (e.g.,
vitamin E deficiency).
Triacylglycerols

o A triacylglycerol. Note that carbons 1 and 3 of the glycerol moiety are not
identical. The broad end of each arrowhead is closer to the reader than the
narrow, pointed end.
o Structure of a triacylglycerol. Palmitate and stearate are saturated fatty acids
(i.e., they have no double bonds). Oleate is monounsaturated (one double
bond). Polyunsaturated fatty acids have more than one double bond.
o Formed by esterification of fatty acids with glycerol
o Oxidized to CO2 and H2O (9kcal/g)
Phospholipids
o Major membranes component
o Cleaved by phospholipases
o Lung surfactant - Respiratory Distress Syndrome (RDS) LecithinSphingomyelin
ratio (L/S ratio)
Sphingolipids
o Derivatives of ceramide
Sphingomyelin
Galactocerebroside
Ganglioside
o White matter of CNS
o Sphingolipidoses
Tay-Sachs disease
Gauchers (go-SHAYZ) disease
Steroids
o Cholesterol - Most abundant
Precursors for: steroid hormone, Vitamin D, bile acids
The bile salt, cholic acid, and the steroid hormone 17-estradiol are derived
from cholesterol and contain the steroid ring structure.
Eicosanoids
o Short-term signaling molecules
Prostaglandins (PGs)
Thromboxane A2 (TXA2)
Leukotrienes (LTs)
7. Know difference between saturated and unsaturated plus cis and trans fatty
acids as well as the essential fatty acids
Trans FA (Eaidic) Elaidic acid is the principal trans unsaturated fatty acid often found
in partially hydrogenated vegetable oils.
Cis (Oleic Acid) Oleic acid is a cis unsaturated fatty acid that comprises 5580% of
olive oil.
Saturated (Stearic Acid) Stearic acid is a saturated fatty acid found in animal fats
and is the intended product in full hydrogenation. Stearic acid is neither cis nor trans
because it has no double bonds.
8. Know relationship between uric acid, urate and gout. Also define tautomer.
Tautomers are two molecules with the same molecular formula but different connectivity
(constitutional isomers). In other words, molecule which can interconvert in a rapid
equilibrium.
Tautomers of uric acid (C5H4N4O3)

 Gout is caused by build up of sodium urate, which tends to precipitate in joints.

9.

Define

radicals, free radicals and superoxides plus know an example of one

Radicals are compounds that have a single electron
Free Radicals are radicals that exist independently in solution or in a lipid environment
Many enzymes generate radicals as intermediates in reactions, they are usually not
released into the cell to become free radicals.
Superoxides are radicals produced in the cell that is the source of much destruction (such
as O2-)
Example: nitrogen dioxide (NO2) is a potent, reactive, toxic radical present in smog and
cigarette smoke

10.
Name and describe the different nitrogen-containing compounds in the body
Polymer of amino acids
Contain about 16% nitrogen by
weight
Oxidized to CO2, H2O and NH4+
(4kcal/g)

Example of - and -amino acid plus L- and D- configuration. The structure of the
-amino acid alanine (both the D- and L-configuration), and the -amino acid aminobutyrate.

The Nitrogenous Bases

11.
Clinical correlations: understand how the chlorinated aromatic hydrocarbon
environmental toxins behave in
the body
Chlorinated Aromatic Hydrocarbon Environmental toxins: DDT,
CDDs
o Dichlorodiphenyl-trichloroethane - (DDT) was a commonly
used pesticide.
o CDDs are formed as a by-product during the production of
other chlorinated compounds and herbicides.
FIG. 5.25. Environmental toxins. Dichlorodiphenyl-trichloroethane
(DDT) is a member of a class of aromatic hydrocarbons that contains
two chlorinated benzene (phenyl) rings joined by a chlorinated ethane
molecule. Chlorodibenzo-p-dioxins (CDDs) are a related class of more
than 75 chlorinated hydrocarbons that all contain a dibenzo-p-dioxin
(DD) molecule comprising two benzene rings joined via two oxygen
bridges at adjacent carbons on each of the benzene rings. The compound 2,3,7,8tetrachlorodibenzo-p-dioxin, shown previously, is one of the most toxic and the most
extensively studied. Chlorinated dibenzofurans (CDFs) are structurally and toxicologically
related.
12.
Clinical correlations: name the metabolic fuels and their energy content
CARBOHYDRATES - (4kcal/g)
Proteins (4kcal/g)
Lipids (9kcal/g)