CHEM113: BIOCHEMISTRY PRELIMS

02
Prof. Merly Alfafara / Second Semester
Transcriber: Kathleen Venus 23

CARBOHYDRATES
o Carbohydrates in the form of wood are
OUTLINE used for shelter and heating and in making
I. BIOCHEMISTRY – OVERVIEW paper
II. BIOCHEMICAL SUBSTANCE
A. MASS COMPOSITION DATA FOR THE HUMAN MASS COMPOSITION DATA
IIIBODY FOR THE HUMAN BODY
III. OCCURRENCE AND FUNCTIONS OF
CARBOHYDRATES
A. FUNCTIONS OF CARBOHYDRATES IN HUMANS
B. CLASSIFICATION OF CARBOHYDRATES
C. CHIRALITY: HANDEDNESS IN MOLECULES
D. STEREOISOMERISM: ENANTIOMERS AND
IIIIIDIASTEREOMERS
E. DESIGNATING HANDEDNESS USING FISCHER
IIIIIIPROJECTION FORMULAS
F. ISOMERISM
IV. CLASSIFICATION OF MONOSACCHARIDE
A. BIOCHEMICALLY IMPORTANT
IIIIIMONOSACCHARIDE
B. CYCLIC FORMS OF MONOSACCHARIDES
C. REACTIONS OF MONOSACCHARIDES
i. OXIDATION TO ACIDIC SUGARS OCCURRENCE AND FUNCTIONS OF
ii. REDUCTION TO PRODUCE SUGAR CARBOHYDRATES
IIIIIIIIIALCOHOLS - Carbohydrates are the most abundant class of
iii. GLYCOSIDE FORMATION bioorganic molecules on planet Earth
iv. PHOSPHATE ESTER FORMATION - In plants, carbohydrates constitute about 75% by
v. AMINO SUGAR FORMATION mass of dry plant materials
V. DISACCHARIDES - Green (chlorophyll-containing) plants produce
VI. POLYSACCHARIDES carbohydrates via photosynthesis
A. STORAGE POLYSACCHARIDES
B. STRUCTURAL POLYSACCHARIDES
C. ACIDIC POLYSACCHARIDES
VII. GLYCOLIPIDS AND GLYCOPROTEINS: CELL
RECOGNITION - Plants have two main uses for carbodydrates they
VIII. DIETARY CONSIDERATIONS AND produce:
CARBOHYDRATES o Cellulose: serves as structural elements
A. GLYCEMIC FOODS o Starch: provide energy reserves
- Dietary intake of plant materials is the major
BIOCHEMISTRY – OVERVIEW carbohydrate source for humans and animals
- It is the study of the chemical substances found in - The average human diet should ideally about two-
living organisms and the chemical interactions of thirds carbohydrates by mass
these substances with each other
- The knowledge explosion that has occurred in this FUNCTIONS OF CARBOHYDRATES IN HUMANS
field during the last decades of the twentieth century • Carbohydrate oxidation provides energy
and the beginning of the twenty-first century is truly • Carbohydrate storage, glycogen, provides a short-
phenomenal term energy source
• Carbohydrates supply carbon atoms for the
BIOCHEMICAL SUBSTANCE synthesis of other biochemical substances
- It is a chemical substance found within a living • Carbohydrates form part of the structural framework
organism of DNA and RNA molecules
- These substances are divided into two groups: • Carbohydrates linked to lipids are structural
o Bioinorganic substances components of cell membranes
o Bioorganic substances • Carbohydrates linked to proteins function in a
- As isolated compounds, bioinorganic and variety of cell-cell and cell-molecule recognition
bioorganic substances have no life in and of process
themselves
CLASSIFICATION OF CARBOHYDRATES
- Yet when these substances are gathered together
in a cell, their chemical interactions are able to - Most simple carbohydrates have empirical formula
sustain life that fit the general formula CnH2nOn.
- It is estimated that more than half of all organic - Early observation by scientists that the above-
carbon atoms are found in the carbohydrate mentioned formula can also be written as Cn(H2O)n,
materials of plants hydrate of water
- Human uses carbohydrates of the plant kingdom - A carbohydrate is a polyhydroxy aldehyde, a
extend beyond food polyhydroxy ketone, or a compound that yields
Page1

o Carbohydrates in the form of cotton and polyhydroxy aldehydes or polyhydroxy ketones

linens are used as clothing upon hydrolysis.
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
CHIRAL CENTER
H O - An atom in a molecule that has four different groups
C CH2OH tetrahedrally bonded to it
CHIRAL MOLECULE
H C OH C O - A molecule whose mirror images are not
superimposable
HO C H HO C H
ACHIRAL MOLECULE
- A molecule whose mirror images are
H C OH H C OH
superimposable

H C OH H C OH
H
CHO
CH2OH CH2OH

D-glucose D-fructose I C Cl H C OH
iiiiiiiii polyhydroxy aldehyde polyhydroxy ketone
MONOSACCHARIDE Br CH2OH
- Is a carbohydrate that contains a single polyhydroxy
aldehyde or polyhydroxy ketone unit
- Cannot be broken down into simpler units by Bromochloroiodomethane Glyceraldehyde
hydrolysis (addition of water molecule) (chiral organic compound) (simple chiral monosaccharide)
- Pure monosaccharides are water-soluble, white,
crystalline solids
- Examples:
o Glucose
CH3
o Fructose
OLIGOSACCHARIDE
- A carbohydrate that contains two-ten
H3C CH2 CH2 *C CH2 CH3
monosaccharide units covalently bonded to each
other
o Disaccharide: most common type of H
oligosaccharide that contains two 3-Methylhexane
monosaccharide units covalently bonded
to each other
- Example:
Cl
o Sucrose (table sugar) H
POLYSACCHARIDE
- A polymeric carbohydrate that contains many H3C CH2*C CH3
H *C CH3
monosaccharide units covalently bonded to each
other
- Example: OH I
o Cellulose 2-Butanol 1-Chloro-1-iodoethane
o Starch
- Organic molecules, especially monosaccharides,
Upon hydrolysis, oligosaccharides and polysaccharides may contain more than one chiral center
produce monosaccharide units
CHIRALITY: HANDEDNESS IN MOLECULES
HANDEDNESS
CHO
- An important general structure property of most

-
monosaccharide
Two forms: left-handed and right handed (mirror
H C OH
images)
- This property in not restricted to carbohydrates
MIRROR IMAGE
H C OH
- Is the reflection of an
object in a mirror
o Superimposable mirror
CH2OH
image Naturally occurring monosaccharides are almost always
▪ Images that coincide at “right-handed”.
all points when the image
are laid upon each other STEREOISOMERISM: ENANTIOMERS AND
o Nonsuperimposable
DIASTEREOMERS
mirror image
STEREOISOMERS
▪ Images where not all
- Are isomeric molecules that have the same
points coincide when the
molecular formula and sequence of bonded atoms
images are laid upon each
but differ in three-dimensional orientation of their
other – exists in “left-
atoms in space
handed” and “right-handed”
FEATURES THAT GENERATE STEREOISOMERISM:
- Not all molecules possess handedness
- Presence of a chiral center in a molecule
- Any organic molecule that contains a carbon atom
- Presence of “structural rigidity” in a molecule
with four different groups attached to it in a
Page2

tetrahedral orientation possesses handedness

[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
ENANTIONAMERS
CHO CHO
- Are stereoisomers whose molecules are
nonsuperimposable mirror images of each other HO H H OH
- Left- and right-handed forms of a molecule with a
single chiral center are enantiomers
- Came from the Greek word enantios, meaning CH2OH CH2OH
opposite L-Glyceraldehyde D-Glyceraldehyde
DIASTEREOMERS
- Are stereoisomers whose molecules are not mirror D- (dextro) means right and L- (levo) means left.
images of each other
- Examples: There are four stereoisomers for the compound below – two
o Cis-trans isomers of alkenes pairs of enantiomers.
o Cycloalkanes
- Molecules that contain more than one chiral center
can also exist in diastereomeric as well as H2C *C
H *CH C H
enantiomeric forms

CHO CHO CHO CHO OH OH OH O

H C OH HO C H H C OH H C OH CHO CHO CHO CHO

H C OH HO C H HO C H H C OH H OH HO H HO H H OH

H C OH HO C H H OH HO H H OH HO H
H C OH HO C H
CH2OH CH2OH CH2OH CH2OH
CH2OH CH2OH CH2OH CH2OH
First enantiomeric pair Second enantiomeric pair
Enantiomers Diastereomers
In a monosaccharide with more than one chiral carbon:
1. The carbon chain is numbered starting at the
carbonyl group of the molecule
2. The last chiral carbon is used to determine D or L
configuration
CHO CHO CHO CHO
H OH HO H HO H H OH
H OH HO H H OH HO H
CH2OH CH2OH CH2OH CH2OH

D-isomer (A) L-isomer (B) D-isomer (C) L-isomer (D)

D-Erythrose L-Erythrose D-Threose L-Threose

AS DIASTEREOMERS
- A and C
DESIGNING HANDEDNESS USING
- A and D
FISCHER PROJECTION FORMULAS - B and C
- It is a two-dimensional structural notation for - B and D
showing the spatial arrangement of groups about Each of these pairs are epimers – diastereomers whose
chiral centers in molecules molecules differ only in the configuration at one chiral center
- Chiral center is represented as the intersection of
vertical and horizontal lines
- The chiral center, which is almost always carbon, is
not explicitly shown
chiral
CH3 center

H CH3
I
- Example:
o Glyceraldehyde

H2C *CH C H

OH OH
Page3
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
ISOMERISM 2. A pair of enantiomers have the same solubility in an
achiral solvent, such as ethanol, but differing solubilities
in a chiral solvent, such as D-2-Butanol
3. The rate and extent of reaction of enantiomers with
another reactant are the same if the reactant is achiral
but differ if the reactant is chiral
4. Receptor sites for molecules within the body have chirality
associated with them
Examples:
- Spearmint (D-Carvone) and Caraway (L-Carvone)
- D-Epinephrine (perfect fit with the cellular receptor)
and L-Epinephrine

CLASSIFICATION OF MONOSACCHARIDE
- The term saccharide comes from the Latin word for
“sugar”, which is saccharum
ALDOSE
- A monosaccharide that contains an aldehyde
functional group
- A polyhydroxy aldehyde
KETOSE
- A monosaccharide that contains a ketone functional
group
- A polyhydroxy ketone

PROPERTIES OF ENANTIOMERS
- When plane-polarized light is passed through a
solution containing a single enantiomer, the plane of
the polarized light is rotated counterclockwise (to
the left) or clockwise (to the right), depending on the Aldopentose Ketopentose
enantiomer
- The extent of rotation depends on the concentration
of the enantiomer as well as on its identity
- The two enantiomers of a pair rotate the plane-
polarized light the same number of degrees, but in
opposite directions
- Enantiomers are sometimes called optical isomers
OPTICALLY ACTIVE COMPOUND
- A compound that rotates the plane polarized light
- Achiral compound – are optically inactive
- Chiral molecules – optically active
DEXTROROTATORY COMPOUND
- Chiral compound that rotates the plane of polarized
light in a clockwise direction
LEVOROTATORY COMPOUND
- Chiral compound that rotates the plane of polarized
light in a counterclockwise direction
ADDITIONAL NOTATIONS
- (+) means rotation to the right (clockwise)
- (-) means rotation to the left (counterclockwise)
- D-L configuration is not directly related to + and –
designations
- D(+)-Mannose – right-handed isomer that rotates
plane-polarized light in a clockwise direction (to the
right)
INTERACTION BETWEEN CHIRAL COMPOUNDS
- Enantiomeric pair have the same interaction with
achiral molecules and different interactions with
chiral molecules
1. Enantiomers have identical:
- Boiling points
- Melting points
Page4

- Densities
- Intermolecular force strength
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
sugar), a disaccharide consisting of a glucose unit
and galactose unit
- Also called brain sugar because it is a component
of glycoproteins (protein-carbohydrate compounds)
found in brain and nerve tissue
- Also present in the chemical markers that
distinguish various tupes of blood – A, B, AB, and O
D-FRUCTOSE
- Most important ketohexose CH2OH
- Also known as levulose and fruit
sugar C O
- The sweetest-tasting of all sugars
HO H
- Found in fruits and honey
- Sometimes used as dietary sugar H OH
- Different in C-1 and C-2 with D-
Glucose H OH
CH2OH
D-RIBOSE
- An aldopentose
- A component of a variety of complex molecules
such as RNA and ATP
- The compound 2-Deoxy-D-ribose is an important
component in nucleic acid chemistry

CHO CHO
H OH H H
H OH H OH
H OH H OH
CH2OH CH2OH
BIOCHEMICALLY IMPORTANT
D-Ribose 2-Deoxy-D-Ribose
MONOSACCHARIDE
D-GLYCERALDEHYDE AND DIHYDROXYACETONE
- The simplest of the monosaccharides CYCLIC FORMS OF MONOSACCHARIDES
- Are important intermediates in the process of - Experimental evidence indicates that for
glycolysis monosaccharides containing five or more carbon
atoms, such open-chain structures are actually in
equilibrium with two cyclic structures, and the cyclic
CHO CH2OH RECALL:
structures are the predominant forms at equilibrium

- Hemiacetals- both –OH and –OR groups are

attached to the same carbon atom
H OH C O O OH OR'
C + R'OH R C H R C H
R H
OR' OR'
CH2OH CH2OH hemiacetal acetal
D-Glyceraldehyde Dihydroxyacetone geminal geminal
ether/alcohol diether
reducing! non-reducing!
D-GLUCOSE
- Monosaccharides – the –OH and –OR groups are
- Ripe fruits are a good source of CHO
attached to the carbonyl carbon
glucose, which is often referred to
H OH - The cyclic forms of
as grape sugar
monosaccharides
- Other names are dextrose and HO H result from the
blood sugar
ability of their
- The normal glucose in human blood H OH
carbonyl group to
is in the range of 70-100 mg/dL (1
H OH react
dL=100 mL)
intramolecularly
- Cells use glucose as a primary CH2OH with a hydroxyl
source of energy
group
D-GALACTOSE CHO - Cyclization of
- D-Galactose and D-Glucose are
glucose
epimers (C-4) H OH
(hemiacetal)
- Seldom encountered as a free
HO H creates a new chiral center at carbon 1, and the
monosaccharide
presence of this new chiral center produce two
- In the human body, it is synthesized HO H stereoisomers, called α and β isomers
from glucose in the mammary
glands for use in lactose (milk H OH
Page5

CH2OH
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
- In an aqueous solution of D-Glucose, a dynamic - α and β configuration is determined by the position
equilibrium exists among the α, β and open-chain of the –OH group on carbon 1 relative to the
forms, and there is continual interconversion among CH2OH group that determines the D or L series
them - In a β configuration
H OH
CHO
H OH
o CH2OH and the –OH of carbon 1 point on
H OH
HO HO the same direction
HO H
HO
HO H H OH
HO
HO OH - In an α configuration
H OH H OH
H OH H OH H H
o The two groups point in opposite directions
CH2OH
alpha-(+)-glucose beta-(+)-glucose

CH2OH CH2OH
H O H O OH
H
OH H OH H
OH OH OH H - In situations where α and β configuration does not
H OH H OH matter, the –OH group on carbon 1 is placed in a
horizontal position

1
CH2OH

2C O

HO C H
1 CH2OH
3 HOH2C 6 O
H C OH HO
4 5 H 2

H C OH H 4 3 OH
5
OH H
6
CH2OH

D-fructose (linear) -D-fructofuranose

PYRANOSE
- A cyclic monosaccharide that contains a six-atom
ring
FURANOSE
- A cyclic monosaccharide that contains a five-atom
ring REACTIONS OF MONOSACCHARIDES
1. Oxidation to acidic sugars
2. Reduction to sugar alcohols
3. Glycoside formation
4. Phosphate ester formation
5. Amino acid sugar formation

OXIDATION TO ACIDIC SUGARS

- Monosaccharide oxidation can yield three different
types of acidic sugars depending on the oxidizing
agent used

HAWORTH PROJECTION FORMULA

- It is a two-dimensional structural notation that
specifies the three-dimensional structure of a cyclic
form of a monosaccharide
- It is from Walter Norman Haworth
WEAK OXIDIZING AGENT
- Tollen’s and Benedict’s Reagents
- Aldoses are converted into aldonic acid

- The D and L of a monosaccharide is determined by

the position of the terminal CH2OH group on the
highest-numbered ring carbon atom
Page6
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
- Aldoses are reducing sugars GLYCOSIDE FORMATION
o Reduces Ag+ to Ag in Tollen’s Reagent - Reacting between monosaccharide and an alcohol
o Reduces Cu2+ to Cu+ in Benedict’s GLYCOSIDE
Reagent - Is an acetal formed from a cyclic monosaccharide
- A reducing sugar is a carbohydrate that gives a by replacement of the hemiacetal carbon –OH
positive test with Tollen’s and Benedict’s solutions group with an –OR group
- In basic conditions, ketoses also give positive
results with these reagents
- These tests are used to test glucose in the urine
- The color of the strip is compared with a chart to
determine the concentration of the glucose in the
urine sample
STRONG OXIDIZING AGENT
- Oxidize both ends of a monosaccharide at the same
time to produce a dicarboxylic acid, aldaric acid
PHOSPHATE ESTER FORMATION
- The hydroxyl groups of a monosaccharide can react
with inorganic oxyacids to form inorganic esters
- Play important roles in the metabolism of
carbohydrates

- In biochemical systems, enzymes can oxidize the

primary alcohol end of an aldose to produce

AMINO SUGAR FORMATION

- One of the hydroxyl group is replaced with an amino
group
- The three common natural amino sugars:

REDUCTION TO PRODUCE SUGAR ALCOHOLS
- The carbonyl group can be reduced to a hydroxyl
group using hydrogen as the reducing agent –
sugar alcohols
- Amino sugars and their N-acetyl derivatives are
important building blocks of polysaccharides found
in chitin and hyaluronic acid
- N-Acetyl-α-D-glucosamine and N-Acetyl-α-D-
galactosamine
o Are present in the biochemical markers on
red blood cells, which distinguish the
various blood types

D-GLUCITOL
- Common name is D-Sorbitol that is used as
moisturizer in foods and cosmetics
- Used as sweetening agent in chewing gum because
Page7

it cannot be used by bacteria as their food

[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
DISACCHARIDES - Like maltose, cellobiose is a reducing sugar, has
- A monosaccharide that has cyclic forms can react three isomeric forms in aqueous solution, and upon
with an alcohol to form a glycoside hydrolysis produces two D-glucose molecules
- This is the same process in joining two or more
monosaccharide units

LACTOSE
- Is made up of β-D-galactose and a D-glucose unit
joined by β(1→4) glycosidic linkage

CH2OH
GLYCOSIDIC LINKAGE
- Is the bond in a disaccharide resulting from the O OH
 (1-4)
reaction between the hemiacetal carbon atom –OH CH2OH H
group of one monosaccharide and an –OH group OH
OH O O
on the other monosaccharide
- Always carbon-oxygen-carbon bond OH
MALTOSE OH
- Often called malt sugar
- Comes from the breakdown of starch OH
- Common ingredient in baby foods and in malted Lactose
sugar -Lactose - principal carbohydrate in milk.
- Made up of 2 D-Glucose units
o Human: 7%–8% lactose
- A reducing sugar
o cow’s milk: 4%–5% lactose
o Lactose intolerance: a condition in which
people lack the enzyme lactase needed to
hydrolyze lactose to galactose and
glucose.
o Lactase hydrolyzes β(1-4) glycosidic
linkages.
o Deficiency of lactase can be caused by a
genetic defect, physiological decline with
age, or by injuries to intestinal mucosa.
o 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.
o If not treated, galactosemia can cause
mental retardation in infants and even
- The most important chemical reaction of maltose is death.
that of hydrolysis producing 2 D-Glucose units o Treatment involved exclusion of milk and
- Acidic condition is needed or maltase is needed milk products from diet
- The α form of lactose is sweeter to the taste and
more soluble in water than the β form
- The β form can be found in ice cream that has been
stored for a long time; it crystallizers and gives the
CELLOBIOSE ice cream a gritty texture
- Is produced as an intermediate in the hydrolysis of SUCROSE
the polysaccharide cellulose - Has a head-to-head glycosidic linkage between α-
- Like maltose, cellobiose two D-glucose units but D-glucose and β-D-fructose with an α, β(1→2)
has a β(1→4) glycosidic linkage configuration
CH2 OH
CH2OH
O
O OH
CH2OH  (1-4) OH
CH2 OH
H O
O OH OH OH
O OH OH
OH -D-Glucose OH
OH OH  (1-2)
OH + O
Linkage
CH2 OH CH2 OH
OH O OH O

Cellobiose OH OH

CH 2OH CH 2OH

OH OH
Page8

-D-Fructose Sucrose
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
- It is a non-reducing sugar due to the absence of
hemiacetal part in the molecule
- Sucrase, the enzyme needed to break a glucose
molecule, is present in the human body
- It only exists in one form either in solid or in
aqueous solution
POLYSACCHARIDES
- A polysaccharide is a polymer that contains many
monosaccharide units bonded to each other by
glycosidic linkages
- Polysaccharides are often also called glycans
1. The identity of the monosaccharide repeating unit(s) in the
polymer chain.
- Homopolysaccharide
- Heteropolysaccharide
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.
STORAGE POLYSACCHARIDE
- Is a polysaccharide that is a storage form for
monosaccharides and is used as an energy source
in cells
- This is done to lower the osmotic pressure within
cells
- The most important storage polysaccharides are
starch (in plant cells) and glycogen (in animal and
human cells)
- 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:
o Cellulose, starch in plants
o Glycogen in animals
o Chitin in arthropods
STARCH
- A storage polysaccharide is a polysaccharide that is
a storage form for monosaccharides and is used as
an energy source in cells.
- Glucose is the monomeric unit
- Storage polysaccharide in plants
- Two types of polysaccharide isolated from starch:
- Amylose: Straight chain polymer - 15 -20%
of the starch and has α(1 → 4) glycosidic bonds
o Molecular Mass: 50,000 (up to 1000
glucose units)
AMYLOPECTIN
- Branched chain polymer - 80 - 85 % of the starch
α(1→4) glycosidic bond for straight chain and a
(1→6) for branch
- Molecular Mass: 300,000 (up to 100,000 glucose
units) - higher than amylose
- Human can hydrolyze alpha linkage but not beta
linkage
- Iodine is often used for the presence of starch in
solution
- Starch-containing solutions turn a dark blue-black
when iodine is added
- As starch is broken down through acid or enzymatic
hydrolysis to glucose monomers, the blue-black
color disappears
GLYCOGEN
- Contains only glucose units
- Sometimes referred to as animal starch
- Liver cells and muscle cells are the storage sites for
glycogen in humans
- Muscle tissue – approximately 1% glycogen
- Liver tissue – 2-3% glycogen
- This amount is enough to take care the demands of
the body for 15 hours
- During strenuous activities, glycogen supplies can
be exhausted rapidly thus the body begins to
oxidize fat as a source of energy
- Athletes do “carbohydrate loading”
- When excess glucose is present in the blood, the
liver and the muscle tissue convert the excess
glucose to glycogen for storage
- Whenever the glucose blood level drops, some
stored glycogen is hydrolyzed back to glucose
- Formation of glycogen reduces osmotic pressure
within the cells and prevents it from living the cells
STRUCTURAL POLYSACCHARIDES
CELLULOSE
- Linear homopolysaccharide with β(1→4) glycosidic
bond
- Up to 5000 glucose units with molecular mass of
900,000 amu
- Cotton is approximately 95% cellulose and wood is
approximately 50% cellulose
- Humans do not have cellulase that hydrolizes
β(1→4) linkage so humans cannot digest cellulose
- Some animals have bacteria that produces
Page9
cellulase in their guts in order for them to get free
glucose from cellulose
[CHEM113] 2.02 CARBOHYDRATES – Prof. Merly Alfafara
- In humans, it serves as dietary fiber in food – GLYCOLIPIDS AND GLYCOPROTEINS:
readily absorbs water and results in softer stools CELL RECOGNITION
and regular bowel movement
- A glycolipid is a lipid molecule that has one or more
- 23-35 g of dietary fiber is required everyday
HO
carbohydrate (or carbohydrate derivative) units
covalently bonded to it.
HO O O - A glycoprotein is a protein molecule that has one or
OH
HO O O more carbohydrate (or carbohydrate derivative)
OH (1-4) OH units covalently bonded to it.
HO O O
(1-4)
- The lipid or protein part of the glycolipids is
OH OH
O O incorporated into the cell membrane structure and
(1-4)
O OH OH the carbohydrate (oligosaccharide) part functions as
a marker on the outer cell membrane surface
OH
CHITIN - In the human reproductive process, fertilization
- Similar to cellulose in both function and structure involves binding interaction between
- Linear polymer with all b (1 4) glycosidic linkages - oligosaccharide markers on the outer membrane
it has a N-acetyl amino derivative of glucose surface of an ovulated egg and protein receptor
- Function is to give rigidity to the exoskeleton s of sites on a sperm cell membrane
crabs, lobsters, shrimp, insects, and other
arthropods DIETARY CONSIDERATIONS
HO
AND CARBOHYDRATES
O
HO O - Foods high in carbs content constitute over 50% of
OH
HO O
O the diet of most people of the world -- a balanced
O
OH HN dietary food should contain about 60% of
HO O
OH O
carbohydrate:
O HN
O - Corn in South America
O OH HN O o Rice in Asia
HN N-Acetyl o Starchy root vegetables in parts of Africa
O
-D-Glucoseamine o Potato and wheat in North America
O
- Nutritionist divide dietary carbs into two classes:
o Simple carb: dietary monosaccharides or
ACIDIC POLYSACCHARIDES
disaccharides - sweet to taste commonly
-
Acidic polysaccharides: polysaccharides with a
referred to as sugars - 20 % of the energy
repeating disaccharide unit containing an amino
in the US die
sugar and a sugar with a negative charge due to a
o Complex carbs: Dietary polysaccharides --
sulfate or a carboxyl group.
starch and cellulose - normally not sweet
- Structural polysaccharide present in connective
to taste
tissue associated with joints, cartilage, synovial
fluids in animals and humans
o Primary function is lubrication necessary GLYCEMIC FOODS
for joint movement - A developing concern about intake of carbohydrates
o These are heteropolysaccharides - have involves how fast the given dietary carbs are broken
more than one type of monosaccharide down to glucose within the human body
monomers is present. - Glycemic effect refers to:
o Examples: o How quickly carbs are digested
▪ Hyaluronic acid o how high blood glucose rise
▪ Heparin o how quickly blood glucose levels return to
HYALURONIC ACID normal
- Alternating residues of N-acetyl-b-D-glucosamine - Glycemic index (GI) has been developed for rating
and D-glucuronic acid. foods
- Highly viscous - serve as lubricants in the fluid of
joints and part vitreous humor of the eye.

HEPARIN
- An anticoagulant-prevents blood clots.
- Polysaccharide with 15–90 disaccharide residues
per chain.
Page10