For STUDENTS Carbohydrates

Carbohydrates
Section 18.1
Biochemistry – An Overview
The Study of Living Things

• Biochemistry is the study of the chemical substances
found in living organisms and the chemical interactions
of these substances with each other.
• A biochemical substance is a chemical substance found
within a living organism.
• Two types of biochemical substances: bioinorganic
substances and bioorganic substances.
– Bioinorganic substances : water and inorganic salts.
– Bioorganic substances : carbohydrates, lipids,
proteins, and nucleic acids
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Section 18.1
Biochemistry – An Overview
The Study of Living Things

• As isolated compounds, bioinorganic and bioorganic
substances have no life in and of themselves. Yet when
these substances are gathered together in a cell, their
chemical interactions are able to sustain life.
• It is estimated that more than half of all organic carbon
atoms are found in the carbohydrate materials of plants.
• Human uses for carbohydrates of the plant kingdom
extend beyond food. Carbohydrates in the form of cotton
and linen are used as clothing. Carbohydrates in the
form of wood are used for shelter and heating and in
making paper.

Section 18.2
Occurrence and Functions of Carbohydrates
Carbohydrates
• Most of the matter in plants, except water, is
carbohydrate material.
• Carbohydrates account for 75% of dry plant material
and are produced by photosynthesis.
– Cellulose: structural element.
– Starch/glycogen: energy reservoir.
- small amount in human body.
• Plant products are source of carbohydrates.
- Average human diet contains 2/3 of carbohydrates.

Section 18.2
Photosynthesis
• A process in which plants produce carbohydrates using
carbon dioxide, water and solar energy.
Chlorophyll
CO2 + H2O + Solar Energy Carbohydrates + O2
Plant Enzymes

Section 18.2
Functions of Carbohydrates in the Human Body

• Carbohydrate oxidation - provides energy
• Carbohydrate storage, in the form of glycogen, provides a
short-term energy reserve
• Carbohydrates supply carbon atoms for the synthesis of other
biochemical substances (proteins, lipids, and nucleic acids)
• Carbohydrates form part of the structural framework of DNA
and RNA molecules
• Carbohydrates linked to lipids are structural components of
cell membranes
• Carbohydrates linked to proteins function in a variety of cell–
cell and cell–molecule recognition processes

Section 18.3
Classification of Carbohydrates
• Simpler Formula:
– CnH2nOn or Cn(H2O)n (hydrates of C).
– n= number of atoms.
• Carbohydrates are polyhydroxy aldehydes or ketones or
compounds that produce such substances upon
hydrolysis.
Aldehyde Ketone
Polyhydroxy ketone
Polyhydroxy
aldehyde

Section 18.3
Monosaccharide
• Contain single polyhydroxy aldehyde or ketone unit
• They can’t be broken down into simpler substances by
hydrolysis (reaction with water) reactions
• Water soluble, white, crystalline solids
Glucose and fructose

are monosaccharides

Section 18.3
Disaccharides
• Contains 2 monosaccharide units covalently bonded to
each other.
• Disaccharides are crystalline and water soluble
substances
• Table sugar (sucrose) and milk sugar (lactose) are
common disaccharides
• Upon hydrolysis they produce monosaccharides

Section 18.3
Oligosaccharides
• Contains 3-10 monosaccharide units - covalently bonded
to each other
• Free oligosaccharides are less common in nature
• Usually found associated with proteins and lipids in
complex molecules.
– Serve structural and regulatory functions

Section 18.3
Polysaccharides
• Contains many monosaccharide units covalently bonded
• Polymers: May contain a few 100s to > million
monosaccharide units
• Examples:
• Cellulose: Paper, cotton, wood
• Starch: Bread, pasta, potatoes, rice, corn, beans,
peas, etc.

Section 18.8
Classification of Monosaccharides
Monosaccharides
• Classification based on # of carbon atoms:
– Triose --- 3 carbon atoms
– Tetrose -- 4 carbon atoms
– Pentoses – 5 carbon atoms
– Hexoses -- 6 carbon atoms
• Classification based on functional groups:
– Aldoses: Monosaccharides with one aldehyde group
– Ketoses: Monosaccharides with one ketone group
• Combined # of C atoms and functional group:
– Example: Aldohexose: Monosaccharide with aldehyde group
and 6 C atoms

Section 18.8
Most Common Monosaccharides
• Example: CHO CH2OH

– Aldohexose:
H OH O
Monosaccharide with
aldehyde group and 6 C HO H HO H
atoms – D-glucose H OH H OH
– Ketohexose: H OH H OH
Monosaccharide with
CH2OH CH2OH
aldehyde group and 6 C
D-Glucose D-Fructose
atoms – D-fructose (aldohexose) (ketohexose)

Section 18.8
Exercise
Classify each of the following monosaccharides according
to both the number of carbon atoms and the type of
carbonyl group present.

Section 18.8
Glucose and Fructose

CHO
H OH 1. Most abundant in nature

2. Nutritionally
HO H most important
3.H Grape OH fruit good source of glucose (20 - 30%
H
by mass)
OH
-- also named grape sugar, dextrose
and
CH2OH
blood sugar (70 - 100 mg/100 mL of blood)
4.D-Glucose
Six membered cyclic form
(aldohexose)
CH2OH
O 1. Ketohexose
HO H 2. Sweetest tasting of all sugars
H OH
3. Found in many fruits and in honey
H OH
4. Good dietary sugar-- due to higher sweetness
CH2OH
5. Five membered cyclic form
D-Fructose
(ketohexose)

Section 18.9
Biochemically Important Monosaccharides
Galactose and Ribose
1. Milk sugar
2. Synthesize in human
3. Also called brain sugar-- part of brain and
nerve tissue
4. Used to differentiate between blood types
5. Six membered cyclic form
1. Part of RNA
2. Part of ATP
3. Part of DNA
4. Five membered cyclic form

Section 18.9
Cyclic Hemiacetal
Forms of D-Glucose
• Dominant form of
monosaccharides
with 5 or more C
atoms is cyclic -
cyclic forms are in
equilibrium with
open chain form
• Cyclic forms are
formed by the
reaction of carbonyl
group (C=O) with
hydroxyl (-OH)
group on carbon 5

Section 18.9
CHO CHO
H OH HO H
CH2OH CH2OH
D-Glyceroldehyde L-Glyceroldehyde
(-OH on rightside) (-OH on left side)

Section 18.9
Cyclic Hemiacetal Forms of D-Glucose

• 2 forms of D-glucose:
– Alpha-form: -OH of C1 and CH2OH of C5 are on opposite sides
– Beta-form: -OH of C1 and CH2OH of C5 are on same sides
6 6
CH2OH Anomeric CH2OH
O Carbon O OH
5 5
4 1
OH 4 OH
1
2 OH 2
OH OH
3 3 Anomeric
OH OH Carbon
a-D-Glucose b-D-Glucose
– Anomers: Cyclic monosaccharides that differ only in the position

of the substituents on the anomeric carbon atom.

Section 18.9
Practice Exercise
• Which of the monosaccharides glucose, fructose, galactose, and

ribose has each of the following structural characteristics? (There
may be more than one correct answer for a given characteristic)
a. It is a pentose.
b. It is a ketose.
c. Its cyclic form has a 6-membered ring.
d. Its cyclic form has two carbon atoms outside the ring.

Section 18.12
Reactions of Monosaccharides
Oxidation
• Oxidation to acidic sugars: The redox chemistry of
monosaccharides is closely linked to the alcohol
and aldehyde functional groups present in them.
• Oxidation can yield three different types of acidic
sugars depending on the type of oxidizing agent
used:
– Weak oxidizing agents such as Tollens and
Benedict’s solutions oxidize the aldehyde end to
give an aldonic acid.
– A reducing sugar is a carbohydrate that gives a
positive test with Tollens and Benedict’s
solutions.
Section 18.12
Reactions of Monosaccharides
Reduction to Sugar Alcohols

• Reduction to sugar alcohols: The carbonyl group in a
monosaccharide (either an aldose or a ketose) is
reduced to a hydroxyl group using hydrogen as the
reducing agent.
– The product is the corresponding polyhydroxy alcohol
- sugar alcohol.
– Sorbitol - used as moisturizing agents in foods and
cosmetics and as a sweetening agent in chewing
gum

Section 18.13
Disaccharides
• Two monosaccharides can react to form disaccharide

• One monosaccharide act as a hemiacetal and other as
alcohol and the resulting ether bond is a glycosidic
linkage.

Section 18.13
Disaccharides
Cellobiose
• Cellobiose is produced as an intermediate in the
hydrolysis of the polysaccharide cellulose:
– Cellobiose contains two beta - D-glucose
monosaccharide units linked through a beta (14)
glycosidic linkage.
CH2OH
O OH
CH2OH b (1-4)
H
O OH
O
OH
OH
OH
OH
Cellobiose

Section 18.13
Disaccharides
Maltose
• Maltose also known as malt sugar
• Maltose is digested easily by humans because we have
enzymes that can break alpha (14) linkages but not
beta (14) linkages of cellobiose. Therefore cellobiose
cannot be digested by humans.
• Baby foods are rich in maltose.
CH2OH CH2OH
O O
a (14)
OH OH
O OH
OH
OH Maltose OH

Section 18.13
Disaccharides
Lactose
• Lactose is made up of beta-D-galactose unit and a beta-
D-glucose unit joined by a beta (14) glycosidic linkage.
• Milk is rich in lactose disaccharide.
CH2OH
O OH
b (1-4)
CH2OH H
OH
OH O O
OH
OH
OH
Lactose

Section 18.13
Disaccharides
Lactose
• Lactose - principal carbohydrate in milk.
– Human - 7%–8% lactose
– Cow’s milk - 4%–5% lactose
– Lactose intolerance: a condition in which people lack the enzyme
lactase needed to hydrolyze lactose to galactose and glucose.
– Lactase hydrolyzes beta (14) glycosidic linkages.
– Deficiency of lactase can be caused by a genetic defect,
physiological decline with age, or by injuries to intestinal
mucosa.
– When lactose is undigested it attracts water causing fullness,
discomfort, cramping, nausea, and diarrhea. Bacterial
fermentation of the lactose further along the intestinal tract
produces acid (lactic acid) and gas, adding to the discomfort.

Section 18.13
Disaccharides
Sucrose
CH2OH
• Sucrose (table sugar): The O
most abundant of all CH2OH
OH
disaccharides and found in OH OH
O
plants. OH
OH
OH
• It is produced commercially a-D-Glucose
b (1-2)
OH
from the juice of sugar cane CH2OH
+
CH2OH
O
Linkage
OH O
and sugar beets. O
OH
OH
– Sugar cane contains up to CH2OH
CH2OH
20% by mass sucrose OH
OH
– Sugar beets contain up to b-D-Fructose
Sucrose
17% by mass sucrose

Section 18.14
Oligosaccharides
• Carbohydrates that contain 3-10 monosaccharide units

boded to each other via glycosidic linkages.
• Not as common as disaccharides in nature. Generally
present in association with other complex molecules.
• Examples:
• Raffinose: made of one each of galactose, glucose
and fructose.
• Stachyose: made of 2 galactose, 1 glucose and 1
fructose units.
• Commonly found in onions, cabbage, broccoli and
wheat.

Section 18.14
Oligosaccharides
Blood Types
• Human blood is classified into four types: A, B, AB, and
O blood groups:
– The basis for the difference is the type of sugars
(oligosaccharides) present.
– Blood of one type cannot be given to a recipient with
blood of another type.
– A transfusion of wrong blood type can cause the blood
cells to form clumps - a potentially fatal reaction.
– People with type O blood are universal donors, and
those with type AB blood are universal recipients.

Section 18.14
Oligosaccharides
Blood Types
• In the United States type O blood is the most common
and type A the second most common.
• The biochemical basis for the various blood types
involves oligosaccharides present on plasma
membranes of red blood cells.
• The oligosaccharides responsible for blood groups are
D-galactose and its derivatives.

Section 18.14
Oligosaccharides
Other oligosaccharides:
• Solanin - a potato toxin, is a oligosaccharide found in
association with an alkaloid.
– Bitter taste of potatoes is due to relatively higher
levels of solanin.
• The oligosaccharides responsible for blood groups are

D-galactose and its derivatives.

Section 18.15
General Characteristics of Polysaccharides
The Polymer Chain

• Polymers of many
monosaccharide
units bonded with
glycosidic linkages
• Two types:
– Linear and
branched, homo-
and hetero-
polysaccharides

Section 18.15
General Characteristics of Polysaccharides
• Polysaccharides are not sweet and don’t show positive

tests with Tollen’s and Benedict’s solutions whereas
monosaccharides are sweet and show positive tests
• Limited water solubility
• Examples:
– Cellulose, starch in plants
– Glycogen in animals
– Chitin in arthropods

Section 18.16
Storage Polysaccharides
Starch
• A storage polysaccharide is a polysaccharide that is a
storage form for monosaccharides and is used as an
energy source in cells.
• Starch:
– Glucose is the monomeric unit
– Storage polysaccharide in plants
– Two types of polysaccharides isolated from starch:
– Amylose: Straight chain polymer - 15 - 20% of the
starch and has alpha (1  4) glycosidic bonds
– Molecular Mass: 50,000 (up to 1000 glucose units)

Section 18.16
Starch
• Amylopectin:
– Branched chain polymer - 80 - 85 % of the starch
alpha (14) glycosidic bond for straight chain and
alpha (16) for branch
– Molecular Mass: 300,000 (up to 100,000 glucose
units) - higher than amylose
– Amylopectin is digested more readily by humans (can
hydrolyze alpha linkages but not beta linkages)

Section 18.16
Glycogen
– Human and animal storage polysaccharide
– Contains only glucose units
– Branched chain polymer – alpha (14) glycosidic bonds in
straight chains and alpha (16) in branches
– Molecular Mass: 3,000,000 (up to 1,000,000 glucose units)
– Three times more highly branched than amylopectin in starch
– Excess glucose in blood stored in the form of glycogen
Glycogenesis
Glucose Glycogen
Glycogenolysis

Section 18.17
Structural Polysaccharides
Cellulose
• Linear homopolysaccharide with beta (14) glycosidic bond
• Up to 5000 glucose units with molecular mass of ~900,000 amu
– Cotton ~95% cellulose and wood ~50% cellulose
– Humans don’t have enzymes that hydrolyze beta (14) linkages - so
they can not digest cellulose -- animals also lack these enzymes but
they can digest cellulose because they have bacteria in their guts to
hydrolyze cellulose
– It serves as dietary fiber in food-- readily absorbs water and results in
softer stools HO
– 20 - 35 g of dietary fiber is desired everyday O
HO O
OH
HO O O
OH b(1-4) OH
O O
HO
OH b (1-4)
O O OH
OH b(1-4)
O OH
OH
Section 18.17
Structural Polysaccharides
Chitin
– Similar to cellulose in both function and structure
– Linear polymer with all beta (14) glycosidic linkages - it has a
N-acetyl amino derivative of glucose
– Function is to give rigidity to the exoskeletons of crabs, lobsters,
shrimp, insects, and other arthropods
HO
HO O O
OH
HO O
O NAcetyl
OH HN
O O bDGlucoseamine
HO
OH HN O
O O
O OH HN O
HN O

Section 18.18
Acidic Polysaccharides
• Acidic polysaccharides - polysaccharides with a repeating

disaccharide unit containing an amino sugar and a sugar with a
negative charge due to a sulfate or a carboxyl group.
• Structural polysaccharide present in connective tissue associated
with joints, cartilage, synovial fluids in animals and humans
– Primary function is lubrication necessary for joint movement
– These are heteropolysaccharides - have more than one type of
monosaccharide monomers is present.
• Examples:
– Hyaluronic acid
– Heparin

Section 18.18
Acidic Polysaccharides
Hyaluronic Acid and Heparin

• Hyaluronic acid:
– Highly viscous - serve as
lubricants in the fluid of
joints and part of vitreous
humor of the eye.
• Heparin:
– An anticoagulant-prevents
blood clots.
– Polysaccharide with 15–90
disaccharide residues per
chain.

Section 18.19
Dietary Considerations and Carbohydrates
Nutrition
• Foods high in carbohydrate content constitute over 50% of the diet of
most people of the world -- a balanced dietary food should contain
about 60% of carbohydrate:
– Corn in South America
– Rice in Asia
– Starchy root vegetables in parts of Africa
– Potato and wheat in North America
• Nutritionists divide dietary carbohydrates into two classes:
– Simple carbohydrates: dietary monosaccharides or
disaccharides - sweet to taste commonly referred to as sugars -
20 % of the energy in the US diet
– Complex carbohydrates: Dietary polysaccharides -- starch and
cellulose - normally not sweet to taste

Section 18.19
Dietary Considerations and Carbohydrates
Glycemic Foods
• A developing concern about intake of carbohydrates
involves how fast the given dietary carbohydrates are
broken down to glucose within the human body
• Glycemic effect refers to:
– how quickly carbohydrates are digested
– how high blood glucose rises
– how quickly blood glucose levels return to normal
• Glycemic index (GI) has been developed for rating foods

Section 18.20
Glycolipids and Glycoproteins: Cell Recognition
• A glycolipid is a lipid molecule that has one or more

carbohydrate (or carbohydrate derivative) units
covalently bonded to it.
• A glycoprotein is a protein molecule that has one or more

carbohydrate (or carbohydrate derivative) units
covalently bonded to it.
• Such carbohydrate complexes are very important in

cellular functions such as cell-cell recognition, cell
adhesion and cellular communication.

For STUDENTS Carbohydrates

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Carbohydrates

The Study of Living Things

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The Study of Living Things

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Functions of Carbohydrates in the Human Body

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Glucose and fructose

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Most Common Monosaccharides

• Example: CHO CH2OH

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Glucose and Fructose

H OH 1. Most abundant in nature

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Galactose and Ribose

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Cyclic Hemiacetal Forms of D-Glucose

– Anomers: Cyclic monosaccharides that differ only in the position

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• Which of the monosaccharides glucose, fructose, galactose, and

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Reduction to Sugar Alcohols

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• Two monosaccharides can react to form disaccharide

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17% by mass sucrose

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• Carbohydrates that contain 3-10 monosaccharide units

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• The oligosaccharides responsible for blood groups are

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The Polymer Chain

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• Polysaccharides are not sweet and don’t show positive

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• Acidic polysaccharides - polysaccharides with a repeating

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Hyaluronic Acid and Heparin

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• A glycolipid is a lipid molecule that has one or more