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Name: PALANGI, GENESIS B. Submission Date: _____________

Year & Section: BSED 2 (MAJOR IN SCIENCE)
BIOCHEMISTRY (PRELIMS)
MODULE 1 (LESSON 1)

CARBOHYDRATES

LESSON 1. The Occurrence, Characteristics and Classifications of Carbohydrates

ENHANCEMENT ACTIVITY/OUTCOME:
1. What role does chlorophyll play in photosynthesis?
Chlorophyll is vital for photosynthesis, which allows plants to absorb energy from light. Chlorophyll
molecules are specifically arranged in and around photosystems that are embedded in the
thylakoid membranes of chloroplasts. In these complexes, chlorophyll serves two primary
functions. The function of the vast majority of chlorophyll (up to several hundred molecules per
photosystem) is to absorb light and transfer that light energy by resonance energy transfer to a
specific chlorophyll pair in the reaction center of the photosystems. The function of the reaction
center of chlorophyll is to absorb light energy and transfer it to other parts of the photosystem.
2. What are the two major functions of carbohydrates in the plant kingdom?
Two main functions of carbohydrates in plants are:
a) Polysaccharides such as starch serve as storage molecules.
b) Cellulose, a polysaccharide, is used to build the cell wall.
3. Indicate how many monosaccharide units are present in each of the following.
a. Disaccharide - are the smallest form of oligosaccharides and consist of two
monosaccharide units.
b. Oligosaccharide – up to ten monosaccharide residues joined together by glycosidic
linkages.
c. Tetrasaccharide - is made up of two β-1, 4, d glucose units, one β-1, 4, d-glucuronic acid
unit, and one α-L. 1,3-rhamnose unit.
d. Polysaccharide - contain more than ten monosaccharide units, whereas oligosaccharides
contain three to ten monosaccharide units; but the precise cutoff varies somewhat
according to convention.

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LESSON 2: Chirality: Handedness in Molecules

ENHANCEMENT ACTIVITY/OUTCOME:

1. Explain what the terms superimposable and non-superimposable mean.

Superimposable Many objects (including molecules) are indistinguishable from their mirror images,
so they are superimposable.
Non-superimposable Other objects, such as your left and right hands, can be distinguished, they
are non-superimposable. Words like "MOM" are the same as the mirror image but "DAD" is not. 
That's why the word "AMBULANCE" on the front hood of the vehicle looks "odd" unless you are
looking at it in your rear-view mirror.
2. In each of the list of objects, identify/underline those objects that are chiral.
a. Nail, hammer, screwdriver, drill bit
b. Your hand, your foot, your ear, your nose
c. The words TOT, TOOT, POP, PEEP

3. Indicate whether the circled carbon atom in each of the following molecules is a chiral center.

Answers:
a. Not Chiral Center
b. Chiral Center
c. Chiral Center
d. Chiral Center
4. Use asterisks (*) to show the chiral center(s), if any, in the following structures. Then, classify
each of the molecules as chiral or achiral.

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College Department
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Bangued, Abra
College Department
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LESSON 3. Stereoisomerism: Enantiomers and Diastereomers

ENHANCEMENT ACTIVITY/OUTCOME:

1. What is the difference between constitutional isomers and stereoisomers?

Difference Between Constitutional Isomers and Stereoisomers

 Definition
a) Constitutional isomers: Constitutional (structural) isomers are compounds with the same
molecular formula but with a different structure.
b) Stereoisomers: Stereoisomers (spatial isomers) are compounds with the same molecular
formula and functional structure but with a different spatial orientation of the molecules or
their parts.
 Types
a) Constitutional isomers: The constitutional isomers can be skeletal, positional, and functional
group isomers.
b) Stereoisomers: The stereoisomers can be configurational (geometric, optical) and
conformational isomers.
 Arrangement of atoms
a) Constitutional isomers: The arrangement of atoms of constitutional isomers is different.
b) Stereoisomers: The arrangement of atoms of stereoisomers is the same.
 Chirality
a) Constitutional isomers: Chirality is absent in constitutional isomers.
b) Stereoisomers: Chirality is present in stereoisomers.
 Properties
a) Constitutional isomers: Constitutional isomers have significantly different properties.
b) Stereoisomers: Stereoisomers have relatively similar properties.
 Nomenclature
a) Constitutional isomers: Constitutional isomers often have different chemical names.
b) Stereoisomers: Stereoisomers often have the same name with a letter/symbol in front of the
name, for identification of orientation.

2. Both enantiomers and diastereomers are stereoisomers. How do they differ?

Enantiomers Diastereomers
Enantiomers are non-superimposable mirror Diastereomers are also non-superimposable but
images of each other are not mirror images of each other.
Enantiomers are mirror images of each other Diastereomers are not mirrored images of each
which are known as stereoisomers. other which are known as stereoisomers.

All enantiomers have the same physical and All diastereomers have different physical and
chemical properties except, interaction with eight chemical properties.
and interaction with other chiral compounds.
Enantiomers have one or more stereocenters. Diastereomers have two or more than two
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stereocenters.
All Enantiomers pass optical activity. They have Not all Diastereomers pass the optical activity.
equal but opposite angles of rotation. They do not have an equal angle of rotation.
In the Enantiomers the Shapes of molecules are Diastereomers have different molecular shapes.
similar.
Enantiomers are present in pairs. There can be several molecules in Diastereomers.
They always have a different R, S-configuration. They have the same R, S-configuration at least at
one stereocenter.
They cannot be separated by crystallization, They can be separated by fractional distillation,
chromatography, etc. chromatography, etc.
Example: Lactic acid Example: Tartaric acid

3. What are two major structural features that can generate stereoisomerism?

Because carbon forms four bonds, there can be multiple ways to form molecules that follow the
octet rule. Even with only four carbon atoms, there are two possible structures for the carbon
backbone. The carbon atoms can be bonded to make a four-carbon chain (butane) or there can be
a one carbon branch from a three-carbon chain (2-methylpropane). Butane and 2-methylpropane
are structural isomers because they both have the chemical formula C4H10.
4. Explain why cis-trans isomers are diastereomers rather than enantiomers?

Stereoisomers can be subdivided into two types: enantiomers and diastereomers.

Enantiomers are stereoisomers whose molecules are nonsuperimposable mirror images of each
other. Left- and right-handed forms of a molecule with a single chiral centre 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.

Cis-trans isomers are diastereomers because if we rotate 180o the mirror image of a cis-trans
isomer we gain the identical compound. We use cis-trans isomerism only to express the relation
between two substituents in a cycloalkane or alkene.

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LESSON 4: Designating Handedness using Fischer Projection Formulas

ENHANCEMENT ACTIVITY/OUTCOME:

 Perform as indicated.

1. What is Fischer projection formula? How to draw the mirror image of a Fischer projection
structure?
A Fischer projection or Fischer projection formula is a convention used to depict a stereo formula in
two dimensions without destroying the stereochemical information, i.e., absolute configuration, at
chiral centers.
You draw the groups on the other side of the vertical line, Enantiomers are mirror images of each
other. If you have the structure for one isomer, you just draw its mirror image to get the enantiomer.
With a Fischer projection, you simply exchange for the groups on either side of the vertical line.
2. Draw the Fischer projection formula for each of the following molecules.

3. Draw a Fischer projection formula for the enantiomer of each of the following
monosaccharides. Then classify each of the molecules as a D enantiomer or an L
enantiomer.

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4. Characterize the members of each of the following pairs of structures as (1) enantiomers,
(2) diastereomers, or (3) neither enantiomers nor disastereomers

Answers:
a. Enantiomers
b. Diastereomer 5 dejay
c. Enantiomers
d. Enantiomers

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LESSON 5: Classification of Monosaccharide

ENHANCEMENT ACTIVITY/OUTPUT:

1. Classify each of the following monosaccharides as an aldose or a ketose.

Answers:
a. Aldose
b. Ketose
c. Ketose
d. Ketose

2. Classify each monosaccharide in Problem 1 by its number of carbon atoms and its type of carbonyl
group.
Answers:
a. Aldohexose
b. Ketohexose
c. Ketotriose
d. Kentopentose

3. Using the information in Figures (2 and 3) below, assign a name to each of the monosaccharides in
Problem 1.
Answers:
a. D-Glucose
b. D-Fructose
c. Dihydroxyacetone
d. Erythrulose

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__________________________________________________________________________________

LESSON 6: Biochemically Important Monosaccharides

ENHANCEMENT ACTIVITY/OUTCOME:
Perform as indicated.
1.) Indicate at what carbon atom(s) the structures of each of the following pairs of
monosaccharides differ.
a. D-Glucose and D-galactose
b. D-Glucose and D-fructose
c. D-Glyceraldehyde and dihydroxyacetone
d. D-Ribose and 2-deoxy-D-ribose

Answers:
a. The main difference between glucose and galactose is the position of each hydroxyl group
(-OH) in the 4th carbos is horizontal in the chair confirmation of the glucose. Whereas the
position of hydroxyl group (-OH) in the 4 th carbon is upward in the chair confirmation of the
Galactose.
b. D- Fructose has a primary alcohol at C-1 and a ketone at C-3. And D-glucose has an
aldehyde at C-1 and a secondary alcohol at C-2. This makes them constitutional isomers,
because they have the same formula but a different order of bonding.
c. Glyceraldehyde is an aldehyde, whereas dihydroxyacetone is a Ketone. Moreover,
glyceraldehyde is a chiral compound, and it has two enantiomers, while dihydroxyacetone
does not show chirality.
d. Pentane sugar for RNA is ribose with 5 carbon atoms. Pentose sugar for DNA is
deoxyribose. Ribose has 5 carbon atom only, while two glucoses have 6 carbons.

2.) Indicate which of the terms aldoses, ketoses, hexoses, and aldohexoses apply to both
members of each of the following pairs of monosaccharides. More than one term may
apply in a given situation.
a. D-Glucose and D-galactose
b. D-Glucose and D-fructose

c. D-Galactose and D-fructose

d. D-Glyceraldehyde and D-ribose

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Answers:
a. Aldoses, Hexoses
b. Aldohexos, Ketoses
c. Hexoses, Ketoses
d. Aldoses, Ketoses

3.) Draw the Fischer projection formula for each of the following monosaccharides.
a. D-Glucose
b. D-Glyceraldehyde
c. D-Fructose
d. L-Galactose

4.) To which of the common monosaccharides does each of the following terms apply?
a. Levulose
b. Grape sugar
c. Brain sugar

Answers:
a. Fructose
b. Glucose
c. Galactose

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Bangued, Abra
College Department
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LESSON 7: Cyclic Forms of Monosaccharides

ENHANCEMENT ACTIVITY/OUTCOME:

Perform the following as directed.

1.) The intermolecular reaction that produces the cyclic forms of monosaccharides involves
functional groups on which two carbon atoms in the case of each of the following?
a. D-Glucose
b. D-Galactose
c. D-Fructose
d. D-Ribose

Answers:
a. Aldehyde C atom and the C-5 hydroxyl group
b. Carbon 6 and Carbon 5 (Pentose)
c. Carbon 2 (the Keto group) and carbon 5
d. Carbon 1 (The aldehyde group) and Carbon 4

2.) What is the structural difference between the alpha (α) and beta (β) forms of D-glucose?
They differ only in the direction that -H and -OH groups point on carbon 1. When alpha-
glucose molecules are joined chemically to form a polymer cellulose is formed.

3.) Fructose contains six carbon atoms, and ribose has only five carbon atoms. Why do both of
these monosaccharides have cyclic forms that involve a five-membered ring?
Since Fructose has a ketone functional group, the ring closure occurs at carbon 2. In
the case of fructose, a five numbered ring is formed. The -OH on Carbon 5 is converted
into the ether linkage to close he ring with carbon 2. This makes a 5-member ring four
carbons and one oxygen. And the Ribose is a pentose, five carbons. Therefore, a five
remembered ring is formed. The -OH on carbon 4 is converted into the ether linkage to

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close the ring with carbon 1. This makes a 5-member ring-four carbons and one
oxygen.

4.) The structure of glucose is sometimes written in an open-chain form and sometimes as a cyclic
hemiacetal structure. Explain why either form is acceptable.
In glucose aldehydic and OH groups are present. OH group a fifth carbon of glucose
get added to the aldehydic group, which result in the formation of cyclic hemiacetal
structure. In this, new chiral carbon is formed known as anomeric carbon. Cyclic
structure of glucose resembles pyran, which has six membered heterocyclic ring.

LESSON 8: Haworth Projection Formulas (HPF)

ENHANCEMENT ACTIVITY/OUTCOME:

Perform as indicated.

1. Identify each of the following structures as an α- D-monosaccharide or a β -D-monosaccharide.

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2. Identify whether each of the structures in Problem 1 is that of a hemiacetal.

Answers:
a. Hemiacetal
b. Hemiacetal
c. Hemiacetal
d. Non-Hemiacetal

3. Draw the open-chain form for each of the monosaccharides in Problem 1.

4. Using the information in Figures 1 and 2, assign a name to each of the monosaccharides in
Problem 1.
Answers:
a. Galactose
b. Glucose
c. Ribose
d. Fructose

5. Draw the Haworth projection formula for each of the following monosaccharides.
a. α-D-Galactose

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b. β-D-Galactose
c. α-L-Galactose
d. β-L-Galactose

LESSON 09: Reactions of Monosaccharides

ENHANCEMENT ACTIVITY/OUTCOME:

Perform as indicated.

1. Which of the following monosaccharides is a reducing sugar?

a. D-Glucose - reducing sugar c. D-Fructose – reducing sugar
b. D-Galactose- reducing sugar d. D-Ribose- not reducing sugar

2. In terms of oxidation and reduction, explain what occurs to both D-glucose and Tollens solution
when they react with each other.
As noted above, sugars may be classified as reducing or non-reducing based on their reactivity
with Tollens', Benedict's or Fehling's reagents. If a sugar is oxidized by these reagents it is called
reducing, since the oxidant (Ag(+) or Cu(+2)) is reduced in the reaction, as evidenced by formation
of a silver mirror or precipitation of cuprous oxide. The Tollens' test is commonly used to detect
aldehyde functions; and because of the facile interconversion of ketoses and aldoses under the
basic conditions of this test, ketoses such as fructose also react and are classified as reducing
sugars.
3. Draw structures for the following compounds.
a. Galactonic acid c. Galacturonic acid
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b. Galactaric acid d. Galactitol

4. Indicate whether each of the following structures is that of a glycoside.

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5. For each structure in Problem 4, identify the configuration at the acetal carbon atom as α or β.
a. Methyl-a-D-glucoside
b. Methyl-B-D- glucoside
c. Methyl-a-D- glucoside
d. Methyl-B-D- glucoside

6. Identify the alcohol needed to produce each of the compounds in Problem 4 by reaction of the
alcohol with the appropriate monosaccharide.
a. Carbonyl group
b. Carbonyl group
c. Terminal primary alcohol group
d. Carbonyl group

7. What is the difference in meaning between the term’s glycoside and glucoside?
If two sugar moieties are joined together through ether linkage, then that ether linkage is known
as glyosidic linkage or bond, and if polysaccharides on hydrolysis yields only groups sugar, then
that glycoside bond is termed as glucosidic bond. The anomeric carbon hydroxyl group of
carbohydrate is linked with alcoholic group of any molecule and by the elimination of water
molecule, the glycosidic bond is formed.

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8. Draw structures for the following compounds.

a. Ethyl-β-D-glucoside
b. Methyl-α-D-galactoside

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