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CARBOHYDRATES AND

LIPIDS
PERTEMUAN KE-3

CARBOHYDRATE
Carbohydrates

are one of the three major

classes of biological molecules.


Carbohydrates

are also the most abundant


biological molecules.

Carbohydrates

derive their name from the

general formula (CH2O)n.

Function
Variety

of important functions in living systems:

nutritional

(energy storage, fuels, metabolic


intermediates)

informational

(cell surface of eukaryotes -- molecular


recognition, cell-cell communication)

osmotic
serve

pressure regulation (bacteria)

as a structural component of many organisms, including


thecell walls of bacteria, the exoskeleton of many insects,
and the fibrouscellulose of plants.

Classification of Carbohydrates

The four major types of carbohydrates are:

1) Monosaccharides
2) Disaccharides
3) Oligosaccharides
4) Polysaccharides

These classifications are based on the units (monosaccharides) in the


molecules.

Classification of Carbohydrates

A monosaccharide is the smallest unit of a carbohydrate that cannot be


hydrolyzed to a simpler carbohydrate unit. It is the basic carbohydrate unit
of cellular metabolism.

Glucose is a monosaccharide. Monosaccharides like glucose are important


sources of cellular energy.

Classification of Carbohydrates

A disaccharide yields two monosaccharideseither the same or


differentwhen hydrolyzed.

Disaccharides are often used by plants and animals to transport


monosaccharides from one cell to another.

The monosaccharides and disaccharides generally have names ending


in ose like glucose, sucrose, and lactose.

Monosaccharides and disaccharides are water-soluble carbohydrates,


have a characteristically sweet taste, and are often called sugars.

Classification of Carbohydrates

An oligosaccharide is a carbohydrate with at least two but not more than six
monosaccharide units linked together.

A polysaccharide is a macromolecular substance that can be hydrolyzed to


yield many monosaccharide units.

Polysaccharides are important structural materials in plants and animals.

Classification of Carbohydrates

Carbohydrates can also be classified by the:

a) Number of carbon atoms in the molecule


b) Functional group present in the molecule
c) Spatial orientation of the molecule
d) Optical activity of the molecule

Carbohydrates classified by the: Number of carbon


atoms in the molecule

The monosaccharides shown below are classified based on


the number of carbon atoms in the molecules.
Monosaccharides commonly have three to seven carbon
atoms.

Carbohydrates classified by the: Functional group


present in the molecule
Mononosaccharides can also be classified based on
whether they have the aldehyde or ketone functional
group.
Monosaccharides with a CHO (aldehyde) group are
known as aldoses while those with a C=O (ketone)
group are known as ketoses. The ketone group is
usually on carbon #2.

Carbohydrates classified by the: Spatial orientation of


the molecule

Monosaccharides can be classified based on their spatial orientation


(stereochemistry).
A monosaccharide can be classified as a D or L isomer, depending
on the spatial orientation of the H and OH groups attached to the
carbon atom adjacent to the terminal primary alcohol group.
The D isomer is represented when the OH is written to the right of
this carbon in the Fischer projection formula. The L isomer is
represented when this OH is written to the left.

Sweeteners and Diet


Sucrose represents 40-60% of all sweeteners and is
20-30% of the average caloric intake in the United
States.
Sucrose is hydrolyzed to glucose and fructose to
prevent crystallization in certain food preparations
and in these cases it is known as invert sugar.

Redox Reactions of Monosaccharides


The redox chemistry of carbohydrates is fundamental to
life.
Glucose is the most important carbohydrate in
biochemistry. Almost all cells derive energy from the
oxidation of glucose through glycolysis, citric acid cycle,
and oxidative phosphorylation. The energy yield from the
oxidation of glucose is shown below.

Redox Reactions of Monosaccharides


The Benedict, Barfoed, and Fehling tests are based on the
formation of a brick red copper(I) oxide precipitate as a
positive result while the Tollens test is based on the
formation of a silver mirror.
The Barfoed test is more sensitive in that it can distinguish
a reducing monosaccharide from a reducing disaccharide.
The sugars are oxidized to carboxylic acids and the metal
ions are reduced . . .

Carbohydrates Characterization
Molischs Test : carbohydrate
Benedict s Test : color change indicator for
simple sugars
Fehling Test: Reducing sugars
Barfoeds
Test:
Monosaccharides
and
Oligosaccharides
Seliwanoff Test : Differentiation of Ketose from
Aldose
Iodine Test : Cellulose, Starch, Dextrin

Redox Reactions of Monosaccharides

Redox Reactions of Monosaccharides


Many clinical tests that monitor color change are
based on the oxidation reaction shown here.

Redox Reactions of Monosaccharides


Sugars with the hemiacetal structure can be reduced under
alkaline conditions because the ring opens as shown below
forming an aldehyde group.

Glucose, lactose, and maltose have the hemiacetal


structure and are reducing sugars, but the disaccharide
sucrose is not a reducing sugar because it does not have
the hemiacetal structure.

Molischs Test
Test

for carbohydrate materials

Using 2 ml of test solution in a test tube,


add 2 drops of 1% 1-naphthol, mix and then
allow 2 ml of conc. Sulphuric acid to flow down
the side of the inclined tube to layer under the
mixture. Note the colour at the junction.

Procedure:

Barfoeds Test
Test

for Monosaccharides and Oligosaccharides

Procedure: To 2 ml of a sample solution is placed


in a test tube. 2 ml of Barfoed's reagent is added.
The solution is then heated in a boiling water bath
for three minutes.

Seliwanoff Test
Test

for Differentiation of Ketose from Aldose

Add 0.5 ml of the test solution to 2.5 ml of


the Seliwanoffs reagent. Place the tubes in boiling
water and note the results and continue heating,
observe the colour change at after 1 minute.

Procedure:

Iodine Test

Test for Cellulose, Starch, Dextrin

Add a drop of dil. HCl to 1 ml test solution to


acidify the solution. Add few drops of iodine
solution. Record the colours observed. Gently warm
the solution and then cool it. Note he change.

Procedure:

Fehlings Test
Test

for Monosaccharides and Oligosaccharides

Using 0.5 ml of test solution, mix with


2.0 ml of Fehlings solution in a test tube and
heat the mixture. Red precipitate indicates the
presence of reducing sugar.
Procedure:

Benedicts Test
Test

for Monosaccharides and Oligosaccharides

Using 0.5 ml of test solution, mix with 5 ml


of Benedicts reagent in a test tube and heat the
mixture. Appearance of red precipitate indicate the
presence of reducing sugar.

Procedure:

Polysaccharides Derived from Glucose


There are three types of naturally occurring
polysaccharides. They are cellulose, glycogen, and starch
that are of major importance.

Polysaccharides Derived from Glucose


An important reaction during digestion is the hydrolysis
of starchy foods as shown below.

Starch is not soluble in cold water due to its large size and
will form a colloidal dispersion in hot water.
Starch solutions form a blue-black color in the presence of
free iodine.

Complex Polysaccharides
Complex polysaccharides are found in animal tissue
including glycosaminoglycans and antigens.
Glycosaminoglycans are part of the connective tissue
found in joints such as the knee.
These complex polysaccharides act as shock absorbers
between bones.

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Complex Polysaccharides
Antigens are even more complex polysaccharides and act as
labels to help the immune system differentiate an
animals cells from invading bacteria.
Antigens are found on red blood cells and are used in the
ABO classification system as shown in Figure 27.10 on
the next slide . . .

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Figure 27.10 These are antigens


that are used in the ABO blood
group classification system.

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Lipids: classification,
structure and
biological role.

About Lipids

Natural materials that preferentially extract into


nonpolar organic solvents

Includes fats, oils, waxes, some vitamins and


hormones, some components of membrane

General types: esters (saponifiable) and those that


cant be hydrolyzed

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Why this Chapter?

Lipids are the largest and most diverse class of biomolecules

To examine lipid structure, function, and metabolism

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LIPIDS
Lipids are a class of biological molecules defined
by low solubility in water and high solubility in
nonpolar solvents.
As molecules that are largely hydrocarbon in
nature, lipids represent highly reduced forms of
carbon and, upon oxidation in metabolism, yield
large amounts of energy. Lipids are thus the
molecules of choice for metabolic energy storage.

Classification
By structure:
1. Simple: fats, oils, waxes, steroids.
2. Complex: phospholipids, spingolipids, glygolipids.
3. They derivatives: hormones, fat-solubility
vitamins
On the basis of whether they undergo hydrolysis
reactions in alkaline solution:
4. Saponifiable lipids can be hydrolyzed under
alkaline conditions to yield salts of fatty acids.
5. Nonsaponifiable lipids do not undergo hydrolysis
reactions in alkaline solution.

Biological functions
The

most important role of lipids is as fuel. Thus fat


is the most concentrated form in which potential
energy can be stored.
Since fat is bad conductor of heat, it provides
excellent insulation.
Fat may also provide padding to protect the internal
organs.
Some compounds derived from lipids are important
building blocks of biologically active materials.
Lipoproteins are constituents of cell walls.
One more important function of dietary lipids is that
of supplying the so-called essential fatty acids

Triacylglycerol

Tri-esters of glycerol with three long-chain carboxylic acids, fatty acids.

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Fatty Acids (from Fats and Oils)

Straight-chain (C12 - C20) carboxylic acids

Double bonds are cis-substituted but trans-fatty


acids also occur
A fat or oil in nature occurs as a mixture of many
different triacylglycerols
The most abundant saturated fatty acids are
palmitic (C16) and stearic (C18)

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Unsaturated and Polyunsaturated Fatty


Acids

Oleic (C18 with one C=C) and linolenic (C18 with 3


C=C) are the most abundant unsaturated

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Soap

A mixture of sodium or potassium salts of long-chain


fatty acids produced by alkaline hydrolysis
(saponification) of animal fat with alkali

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Cleansing Action of Soap

The carboxylate end of the long-chain molecule is


ionic and therefore is preferentially dissolved in water
The hydrocarbon tail is nonpolar and dissolves in
grease and oil
Soaps enable grease to be dissolved into water

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Detergents

Hard water contains Mg+2 and Ca+2 that form


insoluble salts with soaps
Synthetic detergents are alkylbenzene sulfonates
that dissolve dirt like soaps but do not form scums
with Mg+2 and Ca+2 .

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Phospholipids

Phospholipids are diesters of H3PO4, phosphoric acid

Phosphoric acid can form monoesters, diesters and


triesters

In general these are known as phosphates

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Phosphoglycerides

Contain a glycerol backbone linked by ester bonds to


two fatty acids and phosphoric acid
Fatty acid residues with C12C20
The phosphate group at C3 has an ester link to an
amino alcohol

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Sphingolipids
The other major group of phospholipids
Sphingosine or a dihydroxyamine backbone
Constituents of plant and animal cell membranes
Abundant in brain and nerve tissue, as coating around
nerve fibers.

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Phosphoglyceride Membranes

Phosphoglycerides comprise the major lipid


component of cell membranes
Nonpolar tails aggregate in the center of a bilayer
Ionic head is exposed to solvent

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Prostaglandins and Other Eicosanoids

C20 lipids that contain a fivemembered ring with two long


side chains

Present in small amounts in all


body tissues and fluids

Many physiological effects

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Prostaglandin Sources

Biosynthesized from arachidonic acid (C20 unsaturated fatty acid)

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Terpenoids

Steam distillation of plant extracts produces


essential oils
Chemically related to compounds in turpentine (from
pine sap) called terpenes and thus called terpenoids
Mostly hydrocarbons (some oxygens) that do not
contain esters (stable to hydrolysis)

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Steroids

Steroids,are another class of nonsaponifiable lipid,


defined by structure
Has four fused rings A, B, C, and D, beginning at the
lower left
Carbon atoms are numbered beginning in the A ring
The six-membered rings are in fixed chair
conformations

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Male Sex Hormones

Testosterone and androsterone are the two most


important male sex hormones, or androgens

Androstanedione is a precursor

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Female Sex Hormones

Estrone and estradiol are the two most important


female sex hormones, or estrogens
Progesterone is the most important progestin,
steroids that function in pregnancy

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Adrenocortical Hormones

Adrenocortical steroids: secreted by the adrenal


glands near the upper end of each kidney
Mineralocorticoids: control tissue swelling by
regulating cellular salt balance
Glucocorticoids: regulation of glucose metabolism
and in the control of inflammation

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LIPID TEST
SOLUBILITY

TEST

SAPONIFICATION
LIEBERMAN-BUCHARD
SALKOWSKI

TEST

TEST

END