BIOCHEMISTRY

CARBOHYDRATES M#2.3.1
Doc Asdala| Sept. 20, 2017
OUTLINE Types of Isomerism

I. Isomers and Epimers A. Structural Isomers

A. Structural Isomerism  Isomers having same molecular formulas but differing
1. Chain isomers in the order in which the individual atoms are
2. Positional isomers connected.
3. Functional group isomers  Same molecular formula, but their atoms have different
B. Stereoisomerism arrangements or bonds
1. Enantiomer  Butane and isobutene habe same # of carbon and
2. Diastereomer hydrogen atoms but has a different structural formula.
II. Chiral Molecules  Types: Chain, potential, functional group isomers
III. Carbohydrates
A. Classification Based on Sugar Unit
1. Monosaccharide
2. Disaccharide
3. Oligosaccharide
4. Polysaccharide
B. Classification of Monosaccharide
1. Based on Functional group
2. Based on Number of Carbons
3. Based on functional group and number
of carbons
C. Fischer Projection on Monosaccharide
IV. Biologically Important Monosaccharide
1. Chain isomers
V. Biologically Important Disaccharide
- Made up of 2 or more carbon or other compounds with
VI. Polysaccharide
the same molecular formula but different atomic
arrangements.
OBJECTIVES:
At the end of the lecture, the student should be able to:
1. Identify isomers and its types
2. Define a chiral carbon
3. Identify the classification of carbohydrates and its
examples
4. Define what is glycemic index

Legend:
Remember Prev ious
Lecturer Book Trans Com
(Exams) Trans 2. Positional isomers
- Differ in the position of the functional groups with
     respect to main chain
- Same functional group, but different position
I. ISOMERS
 Compounds that have the same chemical formula but
different spatial or structural arrangement.
e.g. Fructose, glucose, mannose and galactose
 Carbohydrate isomers that differ in configuration
around only one specific carbon atom are defined as
epimers of each other.

3. Functional group isomers

- Same molecular or chemical formula, different
functional groups
- e.g. ethyl alcohol and dimethyl ether

TRANSCRIBERS || HERNANDEZ, MM. , JUMAW AN CHECKER || Fernandez, M.C.

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B. Stereoisomers
 Isomers have the same molecular formula and the
samestructural formula but differ in the spatial
arrangement of the atoms in the molecule (Optical
isomers)
 Types: Enatiomers, Diastereomers
1. Enantiomers
- Greek: “enantios” + “meros”, opposite + part
- 2 stereoisomers that are nonsuperimposable mirror
images of the another
- Racemases – enzyme that are able to inconvert D
and L isomers.
2. Diasteriomer
- Stereoisomers that are NOT mirror images of each
other
- Cis and Trans isomers are also called Geometric
Isomers
- Cis-isomers have 2 groups on the same direction
- Trans-isomers have point in opposite direction
II. CHIRAL MOLECULES
 Organinc molecule that contains at least 1 carbon with
four different atoms or groups attached is a chiral
molecule and the carbon is said to be a Chiral carbon
Glyceraldehyde
TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ
BIOCHEMISTRY 2021A
A. Fischer Configuration
 Method to represent a 3D molecule using a 2D drawing
 The chiral carbon is centered at the point of
intersection. Horizontal lines represent bonds directed
outward toward the observer while vertical lines are
bonds pointing away
 E.g. CHClBrI molecule
III. CARBOHYDRATES
 Also known as Saccharides
 Most abundant organic compounds in nature
 Molecular compounds containing 3 elements: carbon,
hydrogen, and oxygen (CHO)
 Source and storage form of energy as well as structural
component of cell membrane
 E.g. Glucose, sucrose, starch, and cellulose
 The predominant carbohydrates encountered in the
body are structurally related to the aldotriose
glyceraldehyde and to the ketotriose dihydroxyacetone
 All carbohydrates contain at least 1 assymetrical
(chiral) carbon and are therefore, optically active
CHECKER || Fernandez, M.C. 2
 M#2.5 CARBOHYDRATES BIOCHEMISTRY 2021A

 Simple sugars (fructose, sucrose, lactose)

4. Polysaccharides
 Complex sugars (fibers and starches)  More than 10 monosaccharide units
***longer to be digested, body needs more time to  Tasteless and water-insoluble
release carbs into your blood as glucose
B. Classification of Monosaccharides

1. Based on Functional Group

a. Aldose
- If an aldehyde is present
- Note: ald-prefix indicates aldehyde, -ose suffix
indicates sugar
b. Ketose
- A monosaccharide with a ketone group

A. Classification Based on Sugar Unit

1. Monosaccharide
 Cannot be broken down into smaller carbohydrate
units
 Simple sugars or polyhydroxyaldehydes or
polyhydroxyketones – generally all carbons except
the carbonyl carbon (C=O) contain a bound
hydroxyl group (-OH)
 Fundamental building blocks of all carbohydrates
 Classified based on functional group, the number
of carbon atoms or both
a. Glucose
 Known as dextrose or grape sugar
 Blood Sugar
 Prepared by hydrolysis of glucose or starch
 Can be given IV to patients unable to take
food by mouth
 NOT ALL IV FLUIDS HAVE DEXTROSE
b. Fructose
 Known as levulose or fruit sugar
 Prepared by hydrolysis of sucrose and inulin
c. Galactose
 Isomer of glucose
 Present in some glycoproteins and glycolipids 2. Based on Number of Carbons
a. Triose is a 3-carbon monosaccharide
Three requirements to be considered a b. Tetrose is a 4-C monosaccharide
carbohydrate:
c. Pentose is a 5-C monosaccharide
- At least a 3-carbon backbone
d. Hexose is a 6-C monosaccharide
- An aldehyde or ketone group
- At least two hydroxyl groups

2. Disaccharides
 Contain 2 monosaccharide units
 Glycosidic linkage – bond between two
monosaccharide
 Optically active

3. Oligosaccharides
 3-10 monosaccharide units
 e.g. Raffinose and Stachyose (found in beans and
legumes)

TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ CHECKER || Fernandez, M.C. 3

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3. Based on Functional group and Number of Carbons
a. Ketotetrose – a 4-C monosaccharide with a ketone
group
b. Aldopentose – a 5-C monosaccharide with an aldehyde
group
C.Fischer projections of Monosaccharides
- based on the stereochemistry of the highest
numbered chiral carbon or the chiral carbon most
distant from the carbonyl group
- Usually considers the hydroxyl (-OH) group at the
chiral carbon whether it is found on the left or right.
1. D- isomers- (Dextro “right side” in Latin) the OH group of
the highest numbered chiral carbon is found at the right
2. L- isomers- (Levo “left side” in Latin) the OH group of the
highest numbered chiral carbon is found at the left
Epimers
- A special type of isomerism where 2 different
monosaccharides differ in configuration around1
specific C atom (except the carbonyl carbon)
TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ
BIOCHEMISTRY 2021A
D.Cyclic projection of Monosaccharides
1. ANOMERS (Haworth Projection)
- - Monosaccharides normally occur in cyclic form in
order to maintain stability wherein C1 and C5 bind
together.
- During a cyclic form, the arrangement of the hydroxyl
group of C1 with respect to the horizontal plane can
vary called anomers
a. α- anomer- hydroxyl group is below the plane (the H is
above)
b. β- anomer- hydroxyl group is above the plane (the H
is below)
**you can also use H as marker wherein α anomer H is
at akyat and β anomers the H is at baba.
IV. Biologically Important Monosaccharides
- C6H12O2 – common formula of monosaccharides
- D- glucose is the most common monosaccharide in
biological system as it is utilized for generation of
ATP and reducing agents
- Glucose is also known as dextrose or blood sugar
- Fructose is also known as fruit sugar
- Ribose and Deoxyribose- sugar found in DNA and
RNA
CHECKER || Fernandez, M.C. 4
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V. Biologically Important Disaccharides
- Formed by dehydration reaction (loss of water) of
two monosaccharides
- Joined by “oxygen bridge” or glycosidic bonds at
specific carbon of the two monosaccharides
A. Sucrose
 Most abundant disaccharide
 Formed by a α,β (1-2) glycosidic linkage between a D-
glucose and β-D-fructose
 Non-reducing sugar since the glycosidic bond was
formed at both anomeric carbons. No free aldehyde
group can reduce the dye/reagent
B. Lactose
 Also called as milk sugar as it is found in high
percentage of dairy milk
 Formed by a β (1-4) glycosidic linkage between β-D-
galactose and D-glucose
 Reducing sugar since there is a free anomeric carbon
(of glucose) that can open to give an aldehyde
TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ
BIOCHEMISTRY 2021A
C.Maltose
 Also called as malt sugar
 Formed by an α (1-4) between 2 d-glucose units
 Reducing sugar since there is a free anomeric carbon
on one of the glucose that can open to give an aldehyde
VI. Polysaccharides
 Polysugars or sugars formed by a large number of
monosaccharide units
 Can be linear or have branches of monosaccharide
units
A. Important polysaccharides
- that differs in the type of glycosidic bonds and the degree of
branching but composed of glucose units
1. Starch
- Primary storage polysaccharide in plants (roots and
stem)
- Most common forms of starch are Amylose and
Amylopectin. Most starches contain 20 to 30%
Amylose and 75-80% Amylopectin
- The breakdown of these polysaccharides will
produce only D-glucose monosaccharides
a. Amylose
Linear or chain type and can contain as many as 4,000
D-glucose units connected by α- 1,4 glycosidic
linkages
b. Amylopectin
Branched-chain and can contain thousands of D-
glucose upon hydrolysis. Linear portion are joined by
α- 1,4 glycosidic linkages while branches are formed
by α- 1,6 glycosidic linkages. Branching usually
occurs every 30 glucose subunits
CHECKER || Fernandez, M.C. 5
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5. Glycosaminoglycans
2. Glycogen - Also called as mucopolysaccharides since it is a
- Major glucose storage molecules in animals complex of carbohydrates containing amino sugars
- Structurally similar to amylopectin in starches but and uronic acids
are highly branched - Precursor of proteoglycans (GAGs attached to
protein) which is an integral part of the ground
substance of connective tissues.

3. Cellulose
- Most abundant organic molecule in nature
- Long, unbranched, D-glucose polymer linked by β
1-4 glycosidic linkages
- Animals can’t hydrolyze cellulose and fibers due to
the lack of enzyme-cellulase

4. Inulin
- Dietary fibers from plants which on hydrolysis,
yields mainly fructose units but are not hydrolyzed
by intestinal enzymes
- Can be used to determine Glomerular Filtration Rate
(GFR)

TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ CHECKER || Fernandez, M.C. 6

 M#2.5 CARBOHYDRATES BIOCHEMISTRY 2021A

6. Glycoproteins
- Also called as mucorproteins which can contain
either branched or unbranched oligosaccharides
which plays a role in maintaining the integrity of cell
membranes.
- Carbohydrates that are commonly found in
glycoproteins are:
- N-acetylclucosamine (GlcNAc) and N-
acetylgalactosamine (GalNaC) which are acetyl
hexosamines
- The carbohydrate can either be attached via O-
linkage (hydroxyl group) or via N-linkage (amino
group)

References:
1. Doc Asdala’s powerpoint
2. Lippincott’s Illustrated Reviews
3. Harper’s Illustrated Biochemistry by Murray et. al

TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ CHECKER || Fernandez, M.C. 7

M#2.5 CARBOHYDRATES BIOCHEMISTRY 2021A

TRANSCRIBERS || HERNANDEZ, MM., JUMAW AN, DQ CHECKER || Fernandez, M.C. 2