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For STUDENTS Carbohydrates
For STUDENTS Carbohydrates
Section 18.1
Biochemistry – An Overview
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.
Photosynthesis
• A process in which plants produce carbohydrates using
carbon dioxide, water and solar energy.
Chlorophyll
CO2 + H2O + Solar Energy Carbohydrates + O2
Plant Enzymes
• 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
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
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
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
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.
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
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)
Exercise
Classify each of the following monosaccharides according
to both the number of carbon atoms and the type of
carbonyl group present.
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)
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
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
CHO CHO
H OH HO H
CH2OH CH2OH
D-Glyceroldehyde L-Glyceroldehyde
(-OH on rightside) (-OH on left side)
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
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.
Copyright © Cengage Learning. All rights reserved 21
Section 18.12
Reactions of Monosaccharides
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 (14)
glycosidic linkage.
CH2OH
O OH
CH2OH b (1-4)
H
O OH
O
OH
OH
OH
OH
Cellobiose
Maltose
• Maltose also known as malt sugar
• Maltose is digested easily by humans because we have
enzymes that can break alpha (14) linkages but not
beta (14) 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
Lactose
• Lactose is made up of beta-D-galactose unit and a beta-
D-glucose unit joined by a beta (14) glycosidic linkage.
• Milk is rich in lactose disaccharide.
CH2OH
O OH
b (1-4)
CH2OH H
OH
OH O O
OH
OH
OH
Lactose
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 (14) 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.
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
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.
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.
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.
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)
Starch
• Amylopectin:
– Branched chain polymer - 80 - 85 % of the starch
alpha (14) glycosidic bond for straight chain and
alpha (16) 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)
Glycogen
– Human and animal storage polysaccharide
– Contains only glucose units
– Branched chain polymer – alpha (14) glycosidic bonds in
straight chains and alpha (16) 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
Cellulose
• Linear homopolysaccharide with beta (14) 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 (14) 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
Copyright © Cengage Learning. All rights reserved 38
Section 18.17
Structural Polysaccharides
Chitin
– Similar to cellulose in both function and structure
– Linear polymer with all beta (14) 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
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
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