Biochemistry

Biochemistry is the branch of

chemistry concerned with the chemical
reactions occurring in living organisms.
Its scope includes such processes as
growth, digestion, metabolism, and
reproduction.
Learning Objectives
• After studying this course, the students
should be able to:
• Familiarize on the concepts of Biochemistry and its
major classes namely Carbohydrates, Proteins,
Lipids, and Nucleic Acids
• Explain the synthesis of micro and macromolecules
and their role in metabolic pathways.
The four major classes of biomolecules upon which
all life depends are:

1 CARBOHYDRATES

2 LIPIDS

3 PROTEINS

4 NUCLEIC ACIDS
4

Carbohydrates

-"hydrates of carbon"
-Most abundant biomolecules in nature.
-A carbohydrate is a biological molecule consisting
of carbon (C), hydrogen (H) and oxygen (O) atoms.
-They are also defined as polyhydroxy aldehydes and
ketones.
5

Carbohydrates
Carbohydrates are the primary molecules responsible
for short-term energy storage in living organisms. They
also form the main structural components of plants.

The many – OH groups make glucose soluble in water

(and therefore in blood), which is important in
glucose’s role as the primary fuel of cells. Glucose is
easily transported in the bloodstream and is soluble
within the aqueous interior of a cell.
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There are three classes of
carbohydrates

Monosaccharides
(oligosaccharide)disaccharides
Polysaccharides

– (the word “saccharide” is derived from the Greek

sakcharon, meaning “sugar”).
7

Monosaccharides
• They are white, crystalline solids that contain a
single aldehyde or ketone functional group.
• Monosaccharides are also called "simple
sugars".
Monosaccharides are the common base unit of
all carbohydrate molecules.

– Characteristics:
Soluble in water
8

Monosaccharides
- are also classified as a triose, tetrose,
pentose, hexose, or heptose on the basis of
whether they contain three, four, five, six, or
seven carbon atoms
 Examples of
Monosaccharides

Trioses: aldotriose and ketotriose

Glyceraldehyde Dihydroxyacetone

Tetroses have either an aldehyde functional group in position 1 (aldotetroses) or

a ketone functional group in position 2 (ketotetroses).
 Examples of
Monosaccharides
Pentoses
Aldopentoses: Ribose, xylose, Ketopentoses: Ribulose, xylulose
arabinose, lyxose
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Examples of
Monosaccharides

Ketohexoses Aldohexoses
psicose  allose
fructose  altrose
sorbose  glucose
Tagatose  mannose
 gulose
 idose
 galactose
 talose
12

KETOHEXOSES
STRUCTURES:
ALDOHEXOSES STRUCTURE
14

ISOMERS
• are compounds that have same chemical
formula but different structures.
Examples: all have chemical formula C6H12O6
• Fructose
• Glucose
• Mannose
• galactose
15

EPIMERS
• carbohydrate isomers that different in
configuration around only one specific
carbon atom.
Examples
• Glucose and galactose C-4 Epimer
• Glucose and mannose C-2 Epimer
16

EPIMERS examples
Formation of cyclic sugars
REACTIONS:

FORMATION OF CYCLIC
 HEMIACETAL FORMATION
SUGARS
 HEMIKETAL FORMATION
18

• Five-membered rings are called "furanoses"

and
• six-membered rings are called "pyranoses".
19

Hemiacetal formation
20

Hemiketal Formation
21

Dissacharides

• Disaccharides consist of (exactly) TWO

(2) monosaccharides joined together.
• A glycosidic bond can form between any hydroxyl
group on the monosaccharide.
• a glycosidic bond or glycosidic linkage is a
type of covalent bond that joins
a carbohydrate (sugar) molecule to another group.
Characteristics:
• Soluble in water
22

Common Dissacharides
SUCROSE (SACCHAROSE)
• glucose + fructose
• Sucrose is table sugar. It is
purified from sugar cane or
sugar beets.
• Formation
• it involves the use of the
alpha form of D-glucose and
the beta form of D-fructose
23

Common Dissacharides
MALTOSE
• glucose + glucose
• Maltose is a sugar found in some
cereals and candies. It is a product of
starch digestions and may be purified
from barley and other grains.
24

Common Dissacharides
LACTOSE
• galactose + glucose
• Lactose is a
disaccharide found in
milk
25

Common Dissacharides

LACTULOSE
• galactose + fructose
• Lactulose is a synthetic (man-made)
sugar that is not absorbed by the
body but is broken down in the colon
into products that absorb water into the
colon, thus softening stools.
• Its primary use is to treat constipation.
It is also used to reduce blood
ammonia levels in persons with liver
disease since lactulose absorbs
ammonia into the colon (removing it
from the body).
26

Common Dissacharides
TREHALOSE
• glucose + glucose
• Trehalose is also known as
tremalose or mycose. It is a
natural alpha-linked
disaccharide with extremely
high water retention
properties.
• In nature, it helps plants and
animals from drying out due
to long periods without water. Trehalose can be found in
shiitake mushrooms and
club moss.
27

Common Dissacharides
CELLOBIOSE
• glucose + glucose
• Cellobiose is a hydrolysis product of cellulose or
cellulose-rich materials, such as paper or cotton.
It is formed by linking two beta-glucose
molecules by a β(1→4) bond.
28

Common Dissacharides
29

Polysaccharides
• Polysaccharides are sugar polymers
containing more than 20 or so monosaccharide
units, and some have hundreds or thousands of
units.
30

Starch
• Starch or amylum is a polysaccharide, a
digestible complex carbohydrate made of
thousands of glucose molecules
• Starch is a mixture of two polysaccharides:
amylose and amylopectin
• Amylose is a linear chain of glucose
molecules; it is poorly soluble in water and
slowly digestible.
• Amylopectin is a branched chain of
glucose molecules; it is more soluble in
water and more easily digestible than
amylose.
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Starch
32
List of Polysaccharides and
Food Examples
POLYSACCHARIDE COMPOSITION FOOD SOURCE

DIGESTIBLE

Starch-storage of Glucose Cereal grains (wheat,

glucose in plants oats, barley, corn,
rice…) and their
products (bread, pasta,
pastries, cookies),
potatoes, tapioca, yam,
legumes
Dextrin (starch gum) Dextrin (starch gum) An artificially produced
food additive

Glycogen (animal Glucose

starch)-storage form of Shellfish, animal liver
glucose in animals
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List of Polysaccharides and
Food Examples

POLYSACCHARIDE COMPOSITION FOOD SOURCE

NON-DIGESTIBLE
(DIETARY FIBER)
Cellulose-Most abundant Glucose Whole grains, green
structural polysaccharide leafy vegetables, beans,
of plants peas, lentils

Hemicellulose Arabinose + xylose Cereals bran

Pectin Various carrots, sweet potatoes;

monosaccharides a food additive
Polydextrose Glucose A food additive
 OTHER POLYSACCHARIDES
• CHITIN
• Principal structural component of the
exoskeletons of arthropods such as insects
and crustaceans
• Also found in the cell walls of many fungi

β(1->4) glycosidic bonds

 The Functions of
Carbohydrates in the Body
• Carbohydrates provides your body with energy.
Your cells convert carbohydrates into the fuel
molecule ATP through a process called cellular
respiration.
• They Also Provide Stored Energy
• Carbohydrate (fibers) promotes good digestive
health by reducing constipation and lowering
the risk of digestive tract diseases.
 Lipids
Lipids are chemical components of the cell that are
insoluble in water but soluble in nonpolar solvents. Lipids
include fatty acids, fats, oils, phospholipids, glycolipids, and
steroids. Insolubility in water makes lipids an ideal structural
component of cell membranes. Lipids make up the containers
that separate the interior of the cell from its external
environment. Lipids are also used for long-term energy
storage and for insulation. We all store extra calories from
food as lipids, some of us more than others.
Five Categories of Lipids:

1 FATS

2 OILS

3 PHOSPHOLIPIDS

4 STEROIDS

5 WAXES
Fats vs Oils

Oils and fats form an important part of a healthy diet. Structurally

they are esters of glycerol with three fatty acids (called either triacylglycerols
or triglycerides). It is these fatty acids that give the functionality to
fats. Chemically, they can be divided into four main types – saturated, cis-
monounsaturated, cis-polyunsaturated and trans fatty acids. In very broad
terms, saturated fatty acids and trans fatty acids are solid at room temperature
while the cis-unsaturates are liquid at room temperature. Although no
naturally occurring fat is either 100% saturated or 100% unsaturated (but is a
mix of the two), fats are often referred to as ‘saturated’ or ‘unsaturated’
because of the predominance of one or other type of fatty acid.
Fats vs Oils
A triglyceride is called a fat if it is a solid at 25°C; it is called an oil if it is
a liquid at that temperature. These differences in melting points reflect
differences in the degree of unsaturation and number of carbon atoms in the
constituent fatty acids. Triglycerides obtained from animal sources are usually
solids, while those of plant origin are generally oils. Therefore, we commonly
speak of animal fats and vegetable oils.
Fatty Acids
FATTY ACIDS
One class of lipids are the fatty acids, carboxylic acids with long hydrocarbon tails.
The general structure for a fatty acid is:

where R represents a hydrocarbon chain containing 3 to 19 carbon atoms. Fatty acids

differ only in their R group. A common fatty acid is myristic acid, where the R group
is CH3(CH2)12-
Fatty Acids

Myristic acid occurs in butterfat and in coconut oil. Myristic acid is an example of
a saturated fatty acid—its carbon chain has no double bonds.

Other fatty acids—called monounsaturated or polyunsaturated fatty acids—have

one or more double bonds, respectively, in their carbon chains. For example, oleic
acid— found in olive oil, peanut oil, and human fat—is an example of a
monounsaturated fatty acid.
 Focus on Health and Medicine

Fats And Oils In The Diet

Fats and oils in our diet come from a variety of sources—meat, dairy products, seeds and nuts,
salad dressing, fried foods, and any baked good or packaged food made with oil. Some fat is required in
the diet. Fats are the building blocks of cell membranes, and stored body fat insulates an organism and
serves as an energy source that can be used at a later time.

In contrast, unsaturated triacylglycerols lower the risk of heart disease by decreasing the amount
of cholesterol in the blood. Unsaturated triacylglycerols from omega-3 fatty acids appear to reduce the
risk of heart attack, especially in individuals who already have heart disease. Dietary recommendations
on fat intake must also take into account trans triacylglycerols, so called trans fats. Trans fats are
formed when liquid oils are partial hydrogenated to form semi-solid triacylglycerols. The three-
dimensional structure of a trans triacylglycerol shows its similarity to saturated triacylglycerols. Like
saturated fats, trans fats also increase the amount of cholesterol in the bloodstream, thus
increasing an individual’s risk of developing coronary artery disease.
 Saturated Fats

Saturated fatty acids have no double bonds in their long

hydrocarbon chains.
 Unsaturated Fats

Unsaturated fatty acids have one or more double bonds in their

long hydrocarbon chains.
Trans Fat
 Phospholipids

The central
architectural feature of
biological membranes is
a double layer of lipids,
which acts as a barrier
to the passage of polar
molecules and ioins.
Membrane lipids are
amphipahtic; one end of
the moleule is
hydrophobic, the other
is hydrophilic.
Phospholipids make-up the cell
membrane.
 Steroids

In addition to their roles as

membrane constituents, the
sterols server as precursors for a
variety of products with specific
Steroids are oxidized derivatives of sterols; biological activities. Steroid
they have the sterol nucleus but lack the hormones for example are potent
alkyl chain attached to ring D of Cholesterol. biological signals that regulate
gene expression.
Bile acids are polar
derivatives of cholesterol that act
as detergents in the intestine,
emulsifying dietary fats to make
them more readily accessible to
digestive lipases.
Example of Steroids
 Cholesterol: In Focus

Cholesterol, the most prominent member of the steroid family, is synthesized

in the liver and found in almost all body tissues. It is a vital component for
healthy cell membranes, and it serves as the starting material for the synthesis
of all other steroids and vitamin D.
 Cholesterol: In Focus
Cholesterol is obtained in the diet from a variety of sources, including meat,
cheese, butter, and eggs. Table below lists the cholesterol content in some
foods. While the American Heart Association currently recommends that the
daily intake of cholesterol should be less than 300 mg, the average American
diet includes 400–500 mg of cholesterol each day

Cholesterol Content in Some Foods

 Cholesterol: In Focus

While health experts agree that the amount of cholesterol in the diet should be
limited, it is also now clear that elevated blood cholesterol (serum cholesterol)
can lead to coronary artery disease. It is estimated that only 25% of the
cholesterol in the blood comes from dietary sources, with the remainder
synthesized in the liver. High blood cholesterol levels are associated with an
increased risk of developing coronary artery disease, heart attack, and stroke.
To understand the relationship between cholesterol and heart disease, we
must learn about how cholesterol is transported through the bloodstream.

Like other lipids, cholesterol is insoluble in the aqueous medium of the blood,
since it has only one polar OH group and many nonpolar C C and C H bonds.
In order for it to be transported from the liver where it is synthesized, to the
tissues, cholesterol combines with phospholipids and proteins to form small
water-soluble spherical particles called lipoproteins.
 In a lipoprotein, the polar heads of phospholipids and the polar portions of protein
molecules are arranged on the surface. The nonpolar molecules are buried in the
interior of the particle. In this way, the nonpolar material is “dissolved” in an aqueous
environment.

Lipoproteins are classified on the basis of their density, with two types being
especially important in determining serum cholesterol levels.

Low-density lipoproteins (LDLs) transport cholesterol from the liver to the

tissues.
High-density lipoproteins (HDLs) transport cholesterol from the tissues back
to the liver.
 Cholesterol: In Focus

HDL particles transport excess cholesterol from

the tissues back to the liver, where it is converted to
other substances or eliminated. Thus, HDLs reduce
the level of serum cholesterol, so HDL cholesterol is
often called “good” cholesterol. Thus, a physical
examination by a physician includes blood work that
measures three quantities: total serum cholesterol,
HDL cholesterol, and LDL cholesterol.

LDL particles transport cholesterol to tissues where it is

incorporated in cell membranes. When LDLs supply more
cholesterol than is needed, LDLs deposit cholesterol on the wall of
arteries, forming plaque. Atherosclerosis is a disease that results from
the buildup of these fatty deposits, restricting the flow of blood,
increasing blood pressure, and increasing the likelihood of a heart
attack or stroke. As a result, LDL cholesterol is often called “bad”
cholesterol.
Atherosclerosis
 Cholesterol: In Focus

Several drugs called statins are now available to reduce the level of
cholesterol in the bloodstream. These compounds act by blocking the
synthesis of cholesterol at its very early stages.

Two examples include atorvastatin (Lipitor) and simvastatin (Zocor).

 Waxes

• A wax is a simple lipid which is an

ester of a long-chain alcohol and a
fatty acid. The alcohol may contain
from 12-32 carbon atoms.
• Waxes are found in nature as
coatings on leaves and stems.
The wax prevents the plant from
losing excessive amounts of water.
• Wax esters are saponified by hot
alkaline solutions and give a fatty acid
and an alcohol.
 Examples of Waxes

• Beeswax - produced by honey bees.

• Chinese wax - produced by the scale
insect Ceroplastes ceriferus.
• Lanolin (wool wax) - from the
sebaceous glands of sheep.
• Shellac wax - from the lac insect
Kerria lacca.
• Spermaceti - from the head cavities
and blubber of the sperm whale.
Waxes
Spermaceti
 References
• Lehninger Principles of Biochemistry Fourth Edition
• www.whfreeman.com/lehninger4e
• Copyright (C) Texas Education Agency, 2012. All rights reserved
• https://www.ifst.org/resources/information-statements/oils-and-fats
• https://chem.libretexts.org/Courses/Eastern_Mennonite_University/EMU%3A_Chemistry_f
or_the_Life_Sciences_(Cessna)/17%3A_Lipids/17.2%3A_Fats_and_Oils
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