Course Code: BIO 024
Student Activity Sheet #1
Name: _____________________________________________________________
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Lesson title: CARBOHYDRATES
Lesson Objectives: by the end of this module, you should be
able to …
1. Know what carbohydrates are.
2. Understand how carbohydrates are formed.
3. Classify and characterize simple carbohydrates,
oligosaccharides, polysaccharides, homoglycans and
heteroglycans.
4. Identify carbohydrate related diseases
Class number: _______
Date:________________
Materials:
Pen, SAS, Snacks
References:
▪
▪
5.
stoker, H. S.
(2017).Biochemistry (3rd ed.).
(M. Finch, Ed.) Belmont CA,
USA
Ferrier, D. (2017). Lippincott's
Illustrated Biochemistry (7th
ed.). Lippincott Williams &
Wilkins,.
Productivity Tip:
Today is quite exciting! Practice this exercise both with your right and left hands. First, imagine that you
have an additional 6th finger. Don’t ask why, just imagine. Second, number your fingers but consider your
index as number 1, middle finger as no. 2, ring finger as no. 3 and pinky as no. 4. Lastly, familiarize in your
head the counting and the position of the exercise. You can try doing it from slow until you get faster. Now, if
you already know how it’s done, teach someone this hand exercise and the importance of it as you finish
this module. Ooopsss…you might want to add some snacks, like Piatos, as you progress with your study
today. Have fun!
0
3
1
1, 3
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2, 3
1, 2
1, 2, 3
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A. LESSON PREVIEW/REVIEW
1) Introduction (3 min)
Carbohydrates are the most abundant class of bioorganic
molecules on planet Earth. Although their abundance in the
human body is relatively low, carbohydrates constitute about
75% by mass of dry plant materials. Green (chlorophyllcontaining) plants produce carbohydrates via photosynthesis.
In this process, carbon dioxide from the air and water from the
soil are the reactants, and sunlight absorbed by chlorophyll is
the energy source.
Chlorophyll
CO2 + H2O + solar energy -----------------→Carbohydrates
Plant enzyme
Plants have two main uses for the carbohydrates they produce. In the form of cellulose, carbohydrates
serve as structural elements, and in the form of starch, they provide energy reserves for the plants.
Dietary intake of plant materials is the major carbohydrate source for humans and animals. The
average human diet should ideally be about two-thirds carbohydrate by mass.
Carbohydrates have the following functions in humans:
1. Carbohydrate oxidation provides energy.
2. Carbohydrate storage, in the form of glycogen, provides a short-term energy reserve
3. Carbohydrates supply carbon atoms for the synthesis of other biochemical substances (proteins,
lipids, and nucleic acids).
4. Carbohydrates form part of the structural framework of DNA and RNA molecules.
5. Carbohydrates linked to lipids are structural components of cell membranes.
6. Carbohydrates linked to proteins function in a variety of cell–cell and cell–molecule recognition
processes.
In this module you will learn how carbohydrates are formed through structural arrangement, the
classification and the uses of the different sugars or carbohydrates. This entails you to review basic
organic chemistry (refer to the table of functional group).
2) Activity 1: What I Know Chart, part 1 (3 mins)
Instructions: "In this chart, reflect on what you know now. Do not worry if you are sure or not sure of
your answers. This activity simply serves to get you started on thinking about our topic. Answer only
the first column, "What I know" based on the question of the second column. Leave the third column
"What I learned" blank at this time.
What I Know
Questions:
1. Carbohydrates are major
sources of sugar for the body.
True or false?
2. Are all carbohydrates sweet?
3. Give at least one medical use
of carbohydrate.
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B.MAIN LESSON:
Activity 2: Content notes (70 min).
Instructions: Please highlight the MOST important information.
Note, it will help if you check the skill building activity first.
A carbohydrate (Cn(H2O)n) is a polyhydroxy aldehyde, a
polyhydroxy ketone, or a compound that yields polyhydroxy
aldehydes or polyhydroxy ketones upon hydrolysis. The
carbohydrate glucose is a polyhydroxy aldehyde, and the
carbohydrate fructose is a polyhydroxy ketone.
CLASSIFICATION OF CARBOHYDRATES
Monosaccharide
• contains a single
polyhydroxy aldehyde or
polyhydroxy ketone unit
• can't be broken down
into simpler units
• ex. Glucose, Fructose
Disaccharide
• contains two
monosaccharide units
covalently bonded to
each other.
• Sucrose (table sugar)
• Lactose (milk sugar)
Oligosaccharide
• contains three to ten
monosaccharide units
covalently bonded to
each other.
• tri,tetra,hexasaccharide
Polysaccharide
• a polymeric
carbohydrate that
contains many
monosaccharide units
covalently bonded to
each other.
• Ex. cellulose, starch
UNDERSTANDING PRINCIPLES ON THE MOLECULAR STRUCTURES OF CARBOHYDRATES
The structures of carbohydrates are far from for being basic and ordinary. However, through the
delicate principles involves from chirality-the handedness in molecules to Haworth projection formulas,
details as to how sugars looks and linked together can be understood in simple yet challenging ways.
MIRROR IMAGES
First, an important property of many molecules, including most
carbohydrates, is “handedness,” which is a form of isomerism. Molecules that
possess “handedness” exist in two forms: a “left-handed” form and a “righthanded” form. These two forms are related to each other in the same way
that a pair of hands is related to each other. The relationship is that of mirror
images. A left hand and a right hand are mirror images of each other.
Objects can be divided into two classes on the basis of their mirror images:
objects with superimposable mirror images and objects with
nonsuperimposable mirror images. Superimposable mirror images are
images that coincide at all points when the images are laid upon each other.
Nonsuperimposable mirror images are images where not all points
coincide when the images are laid upon each other.
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CHIRALITY
Some, but not all, molecules possess handedness. What determines whether or not a molecule
possesses handedness is the presence of a carbon atom that has four different groups bonded to it in a
tetrahedral orientation. The tetrahedral orientation requirement is met only if the bonds to the four
different groups are all single bonds. The handedness-generating carbon atom is called a chiral center.
A chiral center is an atom in a molecule that has four different groups bonded to it in a tetrahedral
orientation. A molecule that contains a chiral center is said to be chiral. A chiral molecule is a
molecule whose mirror images are not superimposable. Chiral molecules have handedness. An achiral
molecule is a molecule whose mirror images are superimposable. Achiral molecules do not possess
handedness.
Has 4 different atoms
bonded to the carbon:
-H,-Cl,-Br,-CH3
Does not have 4 different
atoms or groups bonded to
the carbon:
2 Hydrogens,-CH3,-Br
Has 4 different atoms
bonded to the carbon:
-H,-CH3,-CH2CH3,CH2CH2CH3
Only has 3 atoms
bonded to the carbon:
-H,-CH3, & O w/ double
bond
The Importance of Chirality
In human body chemistry, right-handed and left-handed forms of a molecule often elicit different
responses within the body. Sometimes both forms are biologically active, each form giving a different
response; sometimes both elicit the same response, but one form’s response is many times greater
than that of the other; and sometimes only one of the two forms is biochemically active. For example,
studies show that the body’s response to the right-handed form of the hormone epinephrine is 20 times
greater than its response to the left-handed form.
Monosaccharides, the simplest type of carbohydrate and the building block for more complex types of
carbohydrates, are almost always “right-handed.” Plants, the main dietary source of carbohydrates,
produce only right-handed monosaccharides. Interestingly, the building blocks for proteins, amino
acids, are always left-handed molecules.
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STEREOISOMERISM: ENANTIOMERS and DIASTEREOMERS
The left- and right-handed forms of a chiral molecule are isomers. They are not constitutional
isomers, but rather are stereoisomers. Stereoisomers are isomers that have the same molecular and
structural formulas but differ in the orientation of atoms in space. By contrast, atoms are connected to
each other in different ways in constitutional isomers.
Stereoisomers can be subdivided into two types: enantiomers and diastereomers. Enantiomers
(Enantios- means opposite) are stereoisomers whose molecules are nonsuperimposable mirror images
of each other. Left- and right-handed forms of a molecule with a single chiral center are enantiomers.
Diastereomers are stereoisomers whose molecules are not mirror images of each other. Cis–trans
isomers (of both the alkene and the cycloalkane types) are diastereomers. Molecules that contain more
than one chiral center can also exist in diastereomeric as well as enantiomeric forms.
DESIGNATING HANDEDNESS (D,L) USING FISCHER PROJECTION FORMULAS
Enantiomers are said to be optically active because of the way they interact with plane-polarized
light. An optically active compound is a compound that rotates the plane of polarized light. A
dextrorotatory compound is a chiral compound that rotates the plane of polarized light in a clockwise
direction (means to the right, the Latin dextro means “right). A levorotatory compound is a chiral
compound that rotates the plane of polarized light in a counterclockwise (to the left, the Latin Levo
means “left”) direction
A Fischer projection formula is a two-dimensional structural notation for showing the spatial
arrangement of groups about chiral centers in molecules.
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The D,L system used to designate the handedness of enantiomers is extended to
monosaccharides with more than one chiral center in the following manner. The carbon chain is
numbered starting at the carbonyl group end of the molecule, and the highest-numbered chiral center is
used to determine D or L configuration. Particularly, the –OH group of the highest chiral carbon
determines the configuration. If the –OH is in the right, then it’s a D-isomer and if the –OH is in the left,
and then it’s an L-isomer.
In the present example, compounds A and B (the first enantiomeric pair) are D-erythrose and Lerythrose; compounds C and D (the second enantiomeric pair) are D-threose and L-threose. However,
A and C hass a different relationship since they are epimers. Epimers are diastereomers whose
molecules differ only in the confi guration at one chiral center Other diastereomeric pairs in the present
example are A and D, B and C, and B and D.
STRUCTURES AND CLASSIFICATION OF MONOSACCHARIDE
Although there is no limit to the number of carbon atoms that can be present in a
monosaccharide, only monosaccharides with three to seven carbon atoms are commonly found in
nature. A three-carbon monosaccharide is called a triose, and those that contain four, five, and six
carbon atoms are called tetroses, pentoses, and hexoses, respectively.
Monosaccharides are classified as aldoses or ketoses on the basis of type of carbonyl group
present. An aldose is a monosaccharide that contains an aldehyde functional group. Aldoses are
polyhydroxy aldehydes. A ketose is a monosaccharide that contains a ketone functional group.
Ketoses are polyhydroxy ketones.
C atoms
RCHO
RCOR
RCHO
RCOR
3(C3H6O3)
triose
triulose
glyceraldehyde
dihydroxyacteone
4(C4H8O4)
tetrose
tetrulose
-Erythroluse
5(C5H10O5)
pentose
pentulose
-Erythrose
-Threose
-Ribose
-Arabinose
-Xylose
-Lyxose
-Allose
-Altrose
-Glucose
-Mannose
-Gulose
-Idose
-Galactose
-Talose
6(C6H12O6)
hexose
hexulose
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-Ribulose
-Xylulose
-Psicose
-Fructose
-Sorbose
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Monosaccharides are often classified by both their number of carbon atoms and their functional
group. A six-carbon monosaccharide with an aldehyde functional group is an aldohexose; a five-carbon
monosaccharide with a ketone functional group is a ketopentose. Monosaccharides are also often
called sugars. Hexoses are six-carbon sugars, pentoses five-carbon sugars, and so on. The word
sugar is associated with “sweetness,” and most (but not all) monosaccharides have a sweet taste. The
designation sugar is also applied to disaccharides, many of which also have a sweet taste. Thus sugar
is a general designation for either a monosaccharide or a disaccharide. Saccharide from the latin
Saccharum means sugar.
ALDOSES (D-configuration)
0
1
2
1, 2
3
1, 3
2, 3
1, 2, 3
FAMILIAR???
I know it’s quite challenging. But was it exciting that finally you’ve got to learn that this hand exercise has meaning? Yes, they’re
structures of sugars. First, I told you to imagine having an additional 6th finger. It is because 6 mean the total number of carbon (Hexoses).
Second, numbering your fingers but consider your index as number 1 and not the thumb, because it is in your index finger that the first chiral
carbon is present Lastly, familiarize in your head the counting and the position of the exercise. Zero for the first sugar, Allose, it is because it
doesn’t have any chiral center. Now, you’ve tried doing it but only with your right hand or the right or D-configuration. However, then again
because of its handedness, sugars also have left or L-configuration. Hence, practice this exercise both with your right and left hands and now
you can name them. Let’s see about how ketoses would look like.
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This table shows the possible number of optical isomer that the sugar (aldoses or ketoses) structures
can be made based on the number of chiral centers/carbons and the location of the hydroxyl (-OH)
group in the each of the chiral centers/carbons. The higher the number of chiral center/carbon, the
higher is the possible number of optical isomer.
Carbon atoms
Aldohexose (6c)
Aldopentose (5c)
Aldotetrose (4c)
Ketohexose (6c)
Ketopentose (5c)
Chiral
carbons
4
3
2
3
2
Ruling (Location of –OH in the chiral centers)
optical isomers 2n
2(4) = 16, 8 D & 8 L
2(3) = 8, 4 D & 4 L
2(2) = 4, 2 D & 2 L
2(3) = 8, 4 D & 4 L
2(2) = 4, 2 D & 2 L
▪
▪
▪
▪
1st chiral carbon – OH alternating right and left
2nd chiral carbon – OH alternating 2 rights and 2 lefts
3rd chiral carbon – OH alternating 4 rights and 4 lefts
4th chiral carbon – OH alternating 8 rights and 8 left
THE 16 OPTICAL ISOMER OF ALDOHEXOSES
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KETOSES (D-configuration)
Do you agree that they somehow look the same as aldohexoses? Yes! Although there major difference is
that the second carbon is not a chiral center. Hence, these ketohexose structures that somehow look the
same as other alhohexoses are epimers at carbon 2.
EXAMPLE OF EPIMER:
D - glucose
Aldose
Structure
Hexose
Epimers at C2
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D-mannose
Aldose
Hexose
Epimers at C2
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IMPORTANT SACCHARIDE
Sugar
D-Ribose
(DNA & RNA sugar,
ATP sugar)
Where Found
Nucleic acids (β-dribose
and
β-ddeoxyribose) and ATP
D-Ribulose
Formed in metabolic
processes.
Gum arabic. Plum and
cherry gums.
Wood
gums,
proteoglycans,
glycosaminoglycans.
Heart cells/muscle.
D-Arabinose
D-Xylose
sugar)
(aka
D-Lyxose
L-Xylulose
wood
Intermediate in uronic
acid pathway.
Sugar
D-Glucose
(Grape
sugar,
dextrose,
blood sugar)
D-Fructose
(levulose,
fruit sugar,
dietary
sugar)
Source
Fruit juices. Hydrolysis of
starch,
cane
sugar,
maltose, and lactose.
D-Galactose
(brain sugar)
(just
remember
that
our
brain is a
galaxy
of
information )
D-Mannose
Hydrolysis of lactose.
(disaccharide consisting
of a glucose and a
galactose unit) since this
sugar does not occur free
in nature. Synthesized in
the mammary gland to
make the lactose of milk
Hydrolysis
of
plant
mannans and gums.
Fruit juices. Present in
Honey in equal amount
w/ glucose.
Biochemical Importance
Structural elements of nucleic acids and coenzymes,
eg, ATP, NAD, NADP, flavoproteins. Ribose
phosphates are intermediates in pentose phosphate
pathway (PPP)
Ribulose phosphate is an intermediate in pentose
phosphate pathway (PPP)
Constituent of glycoproteins.
Constituent of glycoproteins.
A constituent of a lyxoflavin isolated from human heart
muscle.
Found in urine in essential pentosuria.
Importance
“Sugar” of the body since blood
contains dissolved glucose. Normal
glucose level 70-100mg/dL
Primary source of cell’s energy.
Can be changed to glucose in the
liver and so used in the body.
Sweetest tasting sugar.
Dietary sugar because less is
needed for the same amount of
sweetness.
- Can be changed to glucose in the
liver and metabolized.
-As brain sugar it is a constituent of
glycolipids and glycoproteins found
in brain and nerve tissue.
- D-galactose is present in chemical
markers that distinguish various
types of blood—A, B, AB, and O
A
constituent
of
many
glycoproteins.
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Clinical Significance
Present in the urine
(glycosuria) in diabetes
mellitus owing to raised
blood
glucose
(hyperglycemia).
Hereditary
fructose
intolerance
leads
to
fructose
accumulation
and hypoglycemia.
Failure to metabolize
leads to galactosemia
and cataract
used
for
preventing
urinary tract infections
(UTIs)
and
treating
carbohydrate-deficient
glycoprotein
syndrome,
an inherited metabolic
disorder.
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CYCLIC MONOSACCHARIDE: HAWORTH PROJECTION FORMULA
Fischer projection formulas are useful for describing the stereochemistry of sugars, but their
long bonds and right-angle bends do not give a realistic picture of the bonding situation in the cyclic
forms, nor do they accurately represent the overall shape of the molecules. Haworth projection
formulas are more useful for those purposes. A Haworth projection formula is a two-dimensional
structural notation that specifies the three-dimensional structure of a cyclic form of a monosaccharide.
The cyclic forms of monosaccharides result from the ability of their carbonyl group to react
intramolecularly with a hydroxyl group. Structurally, the resulting cyclic compounds are cyclic
hemiacetals or hemiketals.
A cyclic monosaccharide containing a six-atom ring is called a pyranose (only aldohexose is
capable), and one containing a five-atom ring is called furanose (aldopentose and ketohexose are
capable of forming) because their ring structures resemble the ring structures in the cyclic ethers pyran
and furan, respectively.
Just like PIATOS, right?
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The hemiacetal carbon atom present in a cyclic monosaccharide structure atom is called the
anomeric carbon atom. An anomeric carbon atom is the hemiacetal carbon atom present in a cyclic
monosaccharide structure. It is the carbon atom that is bonded to an -OH group and to the oxygen
atom in the heterocyclic ring. Cyclic monosaccharide formation always produces two stereoisomers—
an alpha form and a beta form. These two isomers are called anomers. Anomers are cyclic
monosaccharides that differ only in the positions of the substituents on the anomeric (hemiacetal)
carbon atom. The a-stereoisomer has the -OH group on the opposite side of the ring from the -CH2OH
group, and the b-stereoisomer has the -OH group on the same side of the ring as the -CH2OH group.
Note: This pyran form is only for ALDOHEXOSES (bonding C1 & C5)
CYCLIC FORMS OF OTHER MONOSACCHARIDE
FURAN
KETOhexose: C2 & C5
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FURAN
ALDOpentose: C1 & C4
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HAWORTH PROJECTION FORMULA RULES
RULES
ALDOHEXOSES
Edge on oxygen atom ring
D or L isomers:
• Position of CH2OH group of
the highest carbon atom
• D form- CH2OH is aDove
the ring
• L form - CH2OH is beLow
the ring
Alpha or Beta configuration
(anomers)
•
•
•
Determines the –OH position
of the anomeric carbon (C1 or
C2) in relation to the position
of the highest CH2OH.
Alpha – 2 groups are in the
opposite or “apposite”position
Beta – 2 groups are in the
same or “Be same” position
Location of the remaining –OH
• Right –OH = down
(lower down)
• Left –OH = up
(lifted up)
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ALDOPENTOSES
KETOHEXOSES
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EXAMPLE
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REACTIONS OF MONOSACCHARIDE
Five important reactions of monosaccharides are oxidation to acidic sugars, reduction to sugar
alcohols, glycoside formation, phosphate ester formation, and amino sugar formation. Remember,
however, that other aldoses, as well as ketoses, undergo similar reactions.
Oxidation to Produce Acidic Sugars
The
redox
chemistry
of
monosaccharides is closely linked to that of
the alcohol and aldehyde functional groups.
ACIDIC SUGARS
ALDONIC ACID
•Acid group on top
• uses weak oxidizing agent
ALDURONIC ACID
•acid group on bottom
•uses enzymes
ALDARIC ACID
•acid groups both on top
and bottom
•uses strong oxidizing
agent
Reduction to Produce Sugar Alcohols
The carbonyl group present in a monosaccharide (either an aldose or a ketose) can be reduced
to a hydroxyl group, using hydrogen as the reducing agent. For aldoses and ketoses, the product of the
reduction is the corresponding polyhydroxy alcohol, which is sometimes called a sugar alcohol. For
example, the reduction of D-glucose gives D-glucitol.
D-Glucitol aka D-sorbitol have properties similar to those of
the trihydroxy alcohol glycerol. These alcohols are used as
moisturizing agents in foods and cosmetics because of their
affinity for water. D-Sorbitol is also used as a sweetening agent in
chewing gum; bacteria that cause tooth decay cannot use
polyalcohols as food sources, as they can glucose and many other
monosaccharides.
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Glycoside Formation
Hemiacetals were shown to react
with alcohols in acid solution to produce
acetals. Because the cyclic forms of
monosaccharides are hemiacetals, they
react with alcohols to form acetals, like
the reaction of b-D-glucose with methyl
alcohol.
The general name for monosaccharide acetals is glycoside. A glycoside is an acetal formed
from a cyclic monosaccharide by replacement of the hemiacetal carbon -OH group with an -OR group.
It can exist both in alpha and beta form.
Phosphate Ester Formation
The hydroxyl groups of a monosaccharide
can react with inorganic oxyacids to form
inorganic esters. Phosphate esters, formed from
phosphoric acid and various monosaccharides.
For example, specific enzymes in the human
body catalyze the esterifi cation of the hemiacetal
group (carbon 1) and the primary alcohol group
(carbon 6) in glucose to produce the compounds
glucose 1-phosphate and glucose 6-phosphate,
respectively.
These phosphate esters of glucose are stable in aqueous solution and play important roles in
the metabolism of carbohydrates.
Amino Sugar Formation
If one of the hydroxyl groups of a monosaccharide is replaced with an amino group, an amino
sugar is produced. In naturally occurring amino sugars, of which there are three common ones, the
amino group replaces the carbon 2 hydroxyl group. The three common natural amino sugars are.
Amino sugars and their N-acetyl derivatives are important building blocks of polysaccharides
found in chitin and hyaluronic acid. The N-acetyl derivatives of D-glucosamine and D-galactosamine
are present in the biochemical markers on red blood cells, which distinguish the various blood types
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DISACCHARIDES
A monosaccharide that has cyclic forms (hemiacetal forms) can react with an alcohol to form a
glycoside (acetal). This same type of reaction can be used to produce a disaccharide, a carbohydrate in
which two monosaccharides are bonded together. In disaccharide formation, one of the
monosaccharide reactants functions as a hemiacetal, and the other functions as an alcohol.
The bond that links the two monosaccharides of a disaccharide (glycoside) together is called a
glycosidic linkage. A glycosidic linkage is the bond in a disaccharide resulting from the reaction
between the hemiacetal carbon atom -OH group of
one monosaccharide and an -OH group on the other
monosaccharide. It is always a carbon–oxygen–
carbon bond in a disaccharide.
It was noted that a cyclic monosaccharide
contains a hemiacetal (anomeric) carbon atom. Many
disaccharides contain both a hemiacetal carbon atom
and an acetal carbon atom, as is the case for the
preceding disaccharide structure. Hemiacetal and
acetal locations within disaccharides play an important role in the chemistry of these substances.
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Tabulation of disaccharide
Features
Maltose
Common
Names
Malt sugar
(1/3 as sweet
as sucrose)
Source
Structural
Units
Glycosidic
Linkage
Enzymes
for
hydrolysis
Digestion by
amylase or
hydrolysis of
starch.
Germinating
cereals and
malt.
2 Glucose
units
- -D glucose
&
- D-glucose
Cellobiose
Lactose
Sucrose
Cellobiose
Milk sugar
Table sugar
Intermediate in the
hydrolysis of
polysaccharide
cellulose
Milk..
Nursing mother =78%
Cow’s milk = 4-5%
Clinical significance:
In lactase deficiency,
malabsorption leads
to diarrhea and
flatulence. Hence,
lactose intolerance
Juice of sugar cane
(20% by mass) &
sugar beets (17% by
mass)
Clinical significance:
In sucrase deficiency,
malabsorption leads to
diarrhea and
flatulence.
2Glucose units
--D-glucose &
-D- glucose
--D-galactose &
-D- glucose
--D glucose &
--D- fructose
(1-4) (head to
tail)
(1-4) (head to tail)
(1-4) (head to tail)
,(1-2)
(head to head)
Maltase
Cellobiase
Lactase
Sucrase
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OLIGOSACCHARIDES
Are saccharides that contain three to ten monosaccharide units bonded to each other via
glycosidic linkages. Two naturally occurring oligosaccharides found
in onions, cabbage, broccoli, brussel sprouts, whole wheat, and
all types of beans are the trisaccharide raffinose and
the tetrasaccharide stachyose.
TRISACCHARIDE:
RAFFINOSE composed of:
•
•
•
-D-galactose
-D-glucose
-D-fructose
TETRASACCHARIDE:
STACHYOSE composed of:
•
•
•
•
-D-galactose
-D-galactose
-D-glucose
-D-fructose
IMPORTANCE OF OLIGOSACCHARIDES
The type of blood a person has (O, A, B, or AB) is determined by the type of oligosaccharide
that is attached to the person’s red blood cells.
Four monosaccharides contribute to the make-up of the oligosaccharide “marking system.”
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POLYSACCHARIDES
A polysaccharide is a polymer that contains many monosaccharide units bonded to each other
by glycosidic linkages. Polysaccharides are often also called glycans. Glycan is an alternate name for
a polysaccharide. Unlike monosaccharides and most disaccharides, polysaccharides are not sweet.
They have limited water solubility because of their size. However, the -OH groups present can
individually become hydrated by water molecules. The result is usually a thick colloidal suspension of
the polysaccharide in water. Polysaccharides, such as flour and cornstarch, are often used as
thickening agents in sauces, desserts, and gravy.
Parameters to distinguish polysaccharides:
1. The identity of the monosaccharide repeating unit(s) in the polymer chain.
a. Homopolysaccharide/glycan - only one type of monosaccharide monomer
b. Heteropolysaccharide/glycan - with more than one (usually two) type of monosaccharide
monomer
2. The length of the polymer chain.
3. The type of glycosidic linkage between monomer units.
4. The degree of branching of the polymer chain.
TYPES OF POLYSACCHARIDES
A. STORAGE POLYSACCHARIDE : used as an energy source in cells. Examples are starch and
glycogen
GLYCOGEN
STARCH
-energy storage polysaccharide for
-energy storage polysaccharide in plants
animals aka animal starch
Amylose
Amylopectin
• 3x more highly branched than
amylopectin and it is much larger,
• -straight-chain
• -a branched glucose
with up to 1,000,000 glucose units
glucose polymer,
polymer, accounts for the
present.
usually accounts for
remaining 80%–85% of the
15%–20% of the
starch.
starch
• More water soluble
because of increase in
• - with 300-500
monomer units of
branching
glucose
• - contains 100,000 glucose
units
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B. STRUCTURAL POLYSACCHARIDE: serves as a structural element in plant cell walls and animal
exoskeletons like chitin and cellulose.
Cellulose
•
•
•
•
•
the structural component of plant cell walls,
is the most abundant naturally occurring
polysaccharide.
the “woody” portions of plants—stems,
stalks, and trunks—have particularly high
concentrations of this fibrous, waterinsoluble substance.
Contains 5000 glucose units
Nondigestible (human lacks cellulase)
Chitin
•
•
•
•
•
CELLULOSE
CHITIN
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The 2nd most abundant naturally occurring
polysaccharide, next to cellulose.
Function is to give rigidity to the
exoskeletons of crabs, lobsters, shrimp,
insects, and other arthropods.
It also has been found in the cell walls of
fungi.
Structurally identical to cellulose, except the
monosaccharide present is
N-acetyl-D-glucosamine (rather than
glucose)
ND-glucosamine, product of hydrolysis of
chitin, that is marketed as a dietary
supplement touted to decrease joint
inflammation and pain associated w/
osteoarthritis.
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C. ACIDIC POLYSACCHARIDE with a disaccharide repeating unit in which one of the disaccharide
components is an amino sugar and one or both disaccharide components has a negative charge
due to a sulfate group or a carboxyl group. Acidic polysaccharides are heteropolysaccharides.
ex.hyaluronic acid & heparin
HYALURONIC ACID
▪
contains alternating residues of Nacetyl-b-Dglucosamine (NAG) and DGlucuronate
▪
▪
▪
.
D-Glucuronate – is the carboxylate ion
formed when D-glucuronic acid loses its
acidic hydrogen atom.
Highly viscous hyaluronic acid solutions
serve as lubricants in the fluid of joints,
are also associated with the jelly-like
consistency of the vitreous humor of the
eye. (The Greek word hyalos means
“glass”; hyaluronic acid solutions have a
glass-like appearance.)
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HEPARIN
•
•
•
•
•
small highly-sulfated polysaccharide with
only 15–90 disaccharide residues per chain
The source for pharmaceutical heparin is
intestinal or lung tissue of slaughter-house
animals (pigs and cows). Both with negative
charge groups.
Blood anticoagulant. It is naturally present
in mast cells and is released at the site of
tissue injury.
It prevents the formation of clots in the
blood and retards the growth of existing
clots within the blood. It does not, however,
break down clots that have already formed.
The source for pharmaceutical heparin is
intestinal or lung tissue of slaughterhouse animals (pigs and cows).
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SPECIAL GROUP:
GLYCOSAMINOGLYCANS (GAGS)
-aka mucopolysaccharides, or negatively charged polysaccharides. Are large
linear polymers of repeating disaccharide units, commonly containing one or another
amino sugar as one of the monomers in the disaccharide units.
GENERAL ROLE:
▪ mechanical support
▪ cushioning of joints
▪ cellular signals in cell proliferation and cell migration
▪ inhibitors of certain enzymes
LOCATION:
▪ found outside cells
▪ cell surface
▪ part of extracellular matrix
▪ or attached to protein core to form
proteoglycans.
PROTEOGLYCANS:
▪ When glycosamnoglycans are attached to
a protein molecule the compound is called
proteoglycan
[proteoglycans
=
Glycosaminoglycans + proteins]
▪ are more carbohydrate than protein,
hence their properties are mainly
determined by the carbohydrate portion of
the molecule.
▪ The carbohydrate moieties may contain
carboxylic acids or sulfated sugars thus
the GAG chain carry negative charge
PROTEOGLYCAN STRUCTURE: Core protein
strands are heavily modified keratin sulfate and
chondroitin sulfate. The core protein strands are
held in a complex with s strand of hyaluronic acid
by link proteins.
EXAMPLES OF GLYCOSAMINOGLYCANS (GAGS)
▪ chondroitin sulfate
▪ heparin sulfate
▪ keratan sulfate
▪ dermatan sulfate
HEPARAN SULFATE (HS)
▪ sulfated polysaccharide found as a component of cell-surface proteoglycans as a
component of cell-surface proteoglycans in mast cells and in the surface of endothelial cells
lining blood vessels
▪ composed of repeating units of N-acetylglucosamine and uronic acids.
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▪
Class number: _______
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Sulfate ester formation can be found at several positions on these residues and the acetyl
group on N-acetylglucosamine may be replaced by sulfate group (see heparin structure)
FUNCTION: After an injury to tissue, the oligosaccharides derived from this GAG are released
to:
o help mediate the inflammatory response
o promote activity by growth factors, chemokines and cytokines
o recruit leukocytes to the injury site
o as anticoagulant in the form of pentasaccharide sequence, HEPARIN.
NOTE: Heparin is much smaller than heparin sulfate and that is not linked to a protein core. It is
also more sulfated than the average random polysaccharide sequence in heparin sulfate.
CHONDROITIN SULFATE (CS):
▪ contains alternating residues of glucuronic acid and galactose N-acetyl 4-sulfonate
▪ structural polysaccharide of ligaments, cartilage and tendons
▪ ROLE: to lend mechanical support and flexibility to tissue to help form skin and cartilage
DERMATAN SULFATE (DS):
▪ closely related GAG, which is composed of glucuronic acid and N-acetylgalactosamine
▪ structural polysaccharide in skin
KERATAN SULFATE (KS):
▪ formed form alternating units of galactose and sulfated N-acetylgucosamine
▪ found primarily in the cornea of the eye and in joint cartilage for mechanical support and
structural role
▪ structural polysaccharide in nails
OTHER NATURAL POLYSACCHARIDE OF INTEREST
AGAR
▪
▪
▪
▪
▪
INULIN
▪
linear polymer of sulfated and unsulfated galactose prepared form marine algae – agarose
w/ alternating copolymer of galactose and 3,6-anhydrous-galactose
Not a proteoglycan but is purely carbohydrate
When dissolves in hot water and then cooled, it forms gels
Also used as food additive to chicken liquid suspensions
is a polysaccharide of fructose (and hence a fructosan found in tubers and roots of dahlias,
artichokes, and dandelions.
▪ It is readily soluble in water and is used to determine the glomerular filtration rate.
DEXTRINS
▪ are intermediates in the hydrolysis of starch.
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(Lippincott 2017)
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Mucopolysaccharidoses (MPS)- are a group of metabolic disorders caused by the absence or malfunctioning of
lysosomal enzymes needed to break down molecules called glycosaminoglycans (GAGs).
MUCOPOLYSACCHARIDOSES (MPS
Note: Deficiencies in …
1.
2.
Galactosamine 6sulfatase and βgalactosidase that
degrade keratan sulfate
result in Morquio
syndrome (MPS IV), A
and B
Arylsulfatase B that
degrades dermatan
sulfate results in
Maroteaux-Lamy
syndrome (MPS VI).
Degradation of the glycosamino glycan hepararan sulfate by lysosomal enzymes, indicating sites of enzyme
deficiencies in some representative mucopolysaccharidoses (MPS). GlcUA and IdUA= glucuronic and iduronic acids;
GalNAc=N-acetylgalactosamine; GlcNAc=N-acetylglucosamine; GlcN=glucosamine; S=sulfate (Lippincott 2017)
)
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Activity 3: Skill-building Activities (with answer key) (25 mins + 5 mins checking)
A. Matching type: Match column A with the definition in column B
--------------------------------------------------------------------------------------------------------------
COLUMN A:
Terminologies
A. Anomers
B. Stereoisomers
C. Isomers
D. Enantiomers
E. Diastereomers
F. Epimers
G. Chiral molecule
H. Achiral molecule
I. Nonsuperimposable
mirror image
J. Superimposable mirror
image
COLUMN B: Definitions
_____ 1. Compounds that have the same numbers and kinds of
atoms but differ in the way atoms are arranged
_____ 2. Isomers with atoms of the same connectivity that differ
only in the orientation of the atoms in space (L or D)
_____ 3. stereoisomers whose molecules are nonsuperimposable
mirror images of each other
_____ 4. stereoisomers whose molecules are not mirror images of
each other
_____ 5. diastereomers that differ only in the configuration at one
chiral center
_____ 6. are diastereoisomers of cyclic forms of sugars or similar
molecules differing in the configuration (alpha and beta)
_____ 7, Molecule whose mirror images are not superimposable
_____ 8. Molecule whose mirror images are superimposable
_____ 9. Are images that coincide at all points when the images are
laid upon each other
_____ 10. Are images where not all points coincide when the
images are laid upon each other.
STEREOISOMERISM
B. MATCHING TYPE: Characterize the members of each of the following pairs of structure as:
Enantiomer, Diasteriomer, Niether enantiomer nor diasteriomer
-----------------------------------------------------------------------------------------------------------------------------------
A
B
Pairs:
1. A ____________________________
2. B____________________________
3. C ____________________________
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C
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FISCHER PROJECTION FORMULA
C. Instruction: Identify the 1st sugar as D or L isomer. Then draw its mirror image
-----------------------------------------------------------------------------------------------------------------------------------------
D. HAWORTH PROJECTION:
D1: Instruction: Identify the structure of sugar units. ENCIRCLE the letter of your choice.
---------------------------------------------------------------------------------------------------------------------------
1. What is the structure being illustrated?
A. a-D-altrose
B. b-D-altose
C. a-L-altrose
D. b-L-altrose
2. What is the structure being illustrated?
A. a-D-lyxose
B. b-D-lyxose
C. a-L-lyxose
D. b-L-lyxose
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3. What is the structure being illustrated?
A. a-D-tagatose
B. b-D-tagatose
C. a-L-tagatose
D. b-L-tagatose
D2: Instruction: Draw the (4) HAWORTH PROJECTION FORMULA for IDOSE. Label as D or L
isomer and as alpha or beta anomer.
---------------------------------------------------------------------------------------------------------------------------
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E. STRUCTURAL SIMILARITIES and DIFFERENCES
STRUCTURE
FEATURE
w/ or w/o chiral
center
D-glyceraldehyde
Dihydroxyacetone
L or D isomer is
or is not possible
Functional class
(Aldose or
Ketose)
STRUCTURE
FEATURE
Aldose or ketose
D-Fructose
D-glucose
Ribose
Deoxyribose
Hexose or
Pentose
C1 and C2 has
ketone or
aldehyde
STRUCTURE
FEATURE
Aldose or Ketose
Pentose or
tetrose
C2 has oxygen or
deoxygenated
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F. SACCHARIDE
F1:Match the following saccahrides as mono, di, oligo or polysaccharide. Write only the letter before
each number.
----------------------------------------------------------------------------------------------------------------------------COLUMN A:
Saccharide units
A. Monosaccharide
B. Disaccharide
C. Oligosaccharide
D. Polysaccharide
COLUMN B: Examples
_____ 6. Chondroitin sulfate
_____ 7. Starch
_____ 8. Glycogen
_____ 9. Erythrose
_____ 10. Cellobiose
COLUMN B: Examples
_____ 1. Idose
_____ 2. Heparin
_____ 3. Chitin
_____ 4. Dextrin
_____ 5. Psicose
F2: MATCH the letter from Column A on items given in column B and C. Write only the letter before
each number.
COLUMN A:
Saccharides
A. Glucose
B. Galactose
C. Ribose
D. Fructose
E. Xylose
F. Mannose
COLUMN B: OTHER
NAMES
_____ 1. Levulose
_____ 2. Dextrose
_____ 3. Wood sugar
_____ 4. DNA sugar
_____ 5. ATP sugar
_____ 6. Blood sugar
_____ 7. Grape sugar
_____ 8. RNA sugar
_____ 9. Dietary sugar
_____ 10. Fruit sugar
_____ 11. Brain sugar
COLUMN C: SIGNIFICANCE
____ 1. treatment for carbohydrate-deficient
glycoprotein syndrome 1b
____ 2. Is high during the state of
hyperglycemia
____ 3. Failure to metabolize leads to
galactosemia and cataract
____ 4. Another component to make the
disaccharide lactose aside from glucose
____ 5. Present in all 3 disaccharides
____ 6. A structural component of the brain
F3: MATCH the letter from Column A on items given in column B and C. Write only the letter before
each number.
COLUMN A:
Saccharides
A. Maltose
B. Lactose
C. Sucrose
COLUMN B: Composition
____ 1. Glucose + glucose
____ 2. Glucose + Fructose
____ 3. Glucose + Galactose
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COLUMN C: Other names
_____1. Milk sugar
_____2. Malt sugar
_____3. Table sugar
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F4: MATCH the letter from Column A on items given in column B. Then the number from column B with
column C.
COLUMN A:
Classification
A. Acidic
B. Structural
C. Storage
COLUMN B: OTHER
NAMES
_____ 1. Chitin
_____ 2. Starch
_____ 3. Hyaluronic acid
_____ 4. Cellulose
_____ 5. Glycogen
_____ 6. Heparin
COLUMN C: SIGNIFICANCE
_____ A. energy storage polysaccharide of
plants
_____ B. glucose storage polysaccharide in
humans and animals
_____ C. present in woody portion of plant-stem
_____ D. associated with the jelly-like
consistency of the vitreous humor of the eye
_____ E. blood anticoagulant
_____ F. contains alternating residues of Nacetyl-b-Dglucosamine (NAG) and DGlucuronate
used for arthritis
F5: MATCH the letter from Column A on items given in column B. Write only the letter before each
number.
COLUMN A:
glycosaminoglycans
A. chondroitin
sulfate
B. heparin
sulfate
C. keratin
sulphate
D. Dermatan
sulphate
COLUMN C: SIGNIFICANCE
_____ 1. recruit leukocytes to the injury site
_____ 2. structural polysaccharide in nails
_____ 3. which is composed of glucuronic acid and Nacetylgalactosamine
_____ 4. mechanical support and flexibility to tissue to help form
skin and cartilage
_____ 5. structural polysaccharide in skin
Activity 4: What I Know Chart, part 2 (2 mins)
Instruction: To review what was learned from this session, please go back to Activity 1 and
answer the “What I Learned” column. Notice and reflect on any changes in your answers.
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Activity 5: Check for Understanding (10 mins)
Instruction: Now it’s time for you to figure this one out on your own! Take time to read, analyze, and
understand the following questions. For this instance, you will not have the chance to check if you have
the correct answers since there are no more keys to correction.
MULTIPLE CHOICE: WRITE the letter of your choice before each number. Good luck!
1. Which of the following would be correct Haworth projection for b-D-Talose (linear form
is in the left)?
a.
b.
c.
d.
A
B
C
D
2. What is the relationship between the following monosaccharide
a.
b.
c.
d.
1 and 2 are enantiomers, while 2 and 3 are diastereomers
1 and 2 are diastereomers, whiles 2 and 3 are diastereomers
1 and 2 are enantiomers, while 2 and 3 are enantiomers
1 and 2 are diastereomers, while 2 and 3 are enantiomers.
3. Which of the following correctly describes the relationship between galactose and
glucose
a. Glucose is an aldohexose while galactose is a
ketopentose
b. They constitute the structure of the disaccharide
maltose
c. They are epimers at carbon 4
d. They are enantiomers
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4. The only carbohydrate which is NOT having any chiral carbon atom
a.
b.
c.
d.
Erythrose
Erythroluse
Glyceraldehyde
Dihydroxyacetone
5. Carbohydrates that cannot be hydrolyzed to compounds with simpler molecules?
a. Oligosaccharides
b. Monosaccharides
c. Disaccharides
d. Polysaccharides
6. What form must all carbohydrates be in for cells to use them as an energy source
making it the most abundant inside the body?
a. Glycogen
b. Fructose
c. Glucose
b. Ribose
7. Which of the following class of carbohydrates is considered as non-sugar?
a. Disaccharides
b. Monosaccharides
c. Oligosaccharides
d. Polysaccharides
8. Which of the following glycosidic linkage is found in maltose?
a.
b.
c.
d.
Glucose (α-1 – 2β) Fructose
Glucose (α1 – 4) Glucose
Galactose (β1 – 4) Glucose
Glucose (β1 – 4) Glucose
9. Name the major storage form of glucose in animals
a. Cellulose
b. Glycogen
c. Chitin
d. Starch
10. Why are carbohydrates the body\'s preferred source of energy? Because they…
a. Are inexpensive to buy
b. can be used as efficient fuel
c. are long term storage of energy
d. They are plentiful in the diet
11. A pentose sugar reported to be found in heart cells.
a. Xylose
b. Lyxose
c. Ribose
d. Erythrose
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LESSON WRAP-UP
1) Activity 6: Thinking about Learning (5 mins)
A. Work Tracker: You are done with this session! Let’s track your progress. Shade the session
number you just completed.
P1
1
2
P2
3
4
5
6
P3
7
8
9
10
B. Think about your Learning:
Tell me about your thoughts! Today’s topic is all about the carbohydrates.
1. What interests you about the lesson today?
2. Do you have questions in mind that you are interested to be discussed? Please write it down.
___________________________________________________________
___________________________________________________________
___________________________________________________________
________________________________________________________
___________________________________________________________
__________________________________________________________
FAQs
1. What are the negative effects of carbohydrates?
Ans: Refined carbs may increase blood triglycerides, blood sugar levels and cause
insulin resistance. All of these are major risk factors for heart disease and type 2
diabetes.
2. How can carbohydrates lead to diabetes?
Ans: When a person consumes carbohydrates, the digestive system breaks some of them
down into glucose. This glucose enters the blood and raises blood sugar, or glucose, levels.
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When blood glucose levels rise, beta cells in the pancreas release insulin.
Insulin is a hormone that makes our cells absorb blood sugar for energy or storage. As the
cells absorb the blood sugar, blood sugar levels start to drop.
When blood sugar levels drop below a certain point, alpha cells in the pancreas release
glucagon. Glucagon is a hormone that makes the liver release glycogen, a sugar stored in the
liver.
In short, insulin and glucagon help maintain regular levels of blood glucose in cells, especially
the brain cells. Insulin brings excess blood glucose levels down, while glucagon brings levels
back up when they are too low.
If blood glucose levels rise too rapidly, too often, the cells can eventually become faulty and
not respond properly to insulin’s instructions. Over time, the cells need more insulin to react.
We call this insulin resistance.
After producing high levels of insulin for many years, the beta cells in the pancreas can wear
out. Insulin production drops. Eventually it can stop altogether.
.
3. Should carbohydrates be eaten before exercise?
Ans: Ingestion of carbs before exercise is important, mainly for the purpose of topping up
energy stores in muscles and the liver, and so fatigue delay and performance can be
improved by ensuring these stores are high when first beginning exercise. Eating carbs will
therefore be beneficial both during and after exercise, helping you feel the benefits of your
sport and exercise. For high endurance sports it is best to maximise glycogen stores in the
days leading to an event by carbo-loading the few days prior to an event.
4. What happens when all carbs are used?
Ans: Your performance firstly decreases when you skip or use up all your carbs, muscle
movements and motivation both become more difficult, which can then affect performance.
When carb stores have been used up, the body will then use protein as it’s energy source,
which subsequently will affect it’s ability to gain and support muscles. Burning protein as
energy can cause further problems as when your body tries to clean out the byproducts of
protein, your kidneys have to work harder, causing stress which could result in damaging
them. Carbs also help fueling the brain and central nervous system, and when you have run
out of carbs, this can affect their functioning and can in serious cases lead to further
problems.
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KEY TO CORRECTION
A. TERMINOLOGIES
1. C
2.B
3.D
4.E
5.F
6.A
7.G
8.H
9.J
10. I
B. STEREOISOMERISM
Pairs: 1. A: diastereomers 2.B: diastereomers 3.C: Neither enantiomer nor diastereomer
FISCHER PROJECTION FORMULA
G.
-----------------------------------------------------------------------------------------------------------------------------------------
H. HAWORTH PROJECTION:
D1:
---------------------------------------------------------------------------------------------------------------------------
B. b-D-altose
A. a-D-lyxose
A. a-D-tagatose
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D2:
---------------------------------------------------------------------------------------------------------------------------
I.
STRUCTURE
FEATURE
w/ or w/o chiral
center
L or D isomer is
or is not possible
Functional class
(Aldose or
Ketose)
This document is the property of PHINMA EDUCATION
D-glyceraldehyde
Dihydroxyacetone
w/ chiral center
w/o chiral center
Possible
Not possible
Aldose
Ketose
Course Code: BIO 024
Teachers’ Guide Module #1
Name: ____________________________________________________________
Section: ____________ Schedule: ____________________________________
STRUCTURE
FEATURE
Aldose or ketose
Hexose or
Pentose
C1 and C2 has
ketone or
aldehyde
STRUCTURE
FEATURE
Aldose or Ketose
Pentose or
tetrose
C2 has oxygen or
deoxygenated
Class number: _______
Date: _______________
D-Fructose
D-glucose
Ketose
Aldose
Hexose
Hexose
Ketone
Aldehyde
Ribose
Deoxyribose
Aldose
Aldose
Pentose
Pentose
Oxygenated
Deoxygenated
F. SACCHARIDE
ACTIVITY
F1
F2
F3
F4
F5
ANSWERS:
1.A
2.D
3.D
4.D
Column B: 1. D
2.A
3. E
Column c: 1.F 2.A
3.B
4.B
Column b: 1. A
2.C
3.B
Column b: other names: 1.B 2.C
Column c: significance: A. 2 B.5
Column c: significance: 1. B 2.C
5.A
4. C
5.A
3.A
C.4
3.D
This document is the property of PHINMA EDUCATION
6. D 7.D
8.D
5.C
6.A
7.A
6.B
COLUMN C: 1.B
4.B
5.C
6.A
D.3
E.6
F.1
4.A
5.D
9.A 10.B
8.C
9.D
2.A
3.C
10.D
11.B