CARBOHYDRATES

MATERI
1. Pengantar Biokimia dan Pendahuluan
Karbohidrat
2. Katabolisme karbohidrat (I)
3. Katabolisme karbohidrat (II)
4. Biosintesis Karbohidrat
5. Pendahuluan Lipid
6. Katabolisme Lipid
7. Biosintesis Lipid
UAS
 Proporsi penilaian

1. Tugas : 15%
2. Kuis : 15%
3. Ujian (UTS & UAS) : 70%
(UTS 35% & UAS 35%)
 CARBOHYDRATE

Biological Molecules
 CARBOHYDRATE
-Monosaccharides-

The simplest carbohydrate are

monosaccharides.
These are sugars. They include glucose,
fructose, and galactose.
These three monosaccharides each have six
carbon atoms.
So they are also known as hexose sugars.
Their molecular formula is C6H12O6

Biological Molecules
A. MONOSACCHARIDES
• D- and L-
Monosaccharides
•D-Monosaccharide
• has the –OH group
on its penultimate
carbon to the right

•L-Monosaccharide
• has the –OH group
on its penultimate
carbon to the left
A. MONOSACCHARIDES
•Cyclic Structure
• Haworth Projection

•β means that the –OH on the anomeric

carbon lies on the same side of the ring as
the terminal –CH2OH

•α means that the –OH on the anomeric

carbon lies on the side of the ring opposite
from the terminal –CH2OH
D- galaktosa D- fruktosa
 CARBOHYDRATE
-Disaccharides-

Two monosaccharides can link together to

form a disaccharide.
Two glucose molecules can link to produce
maltose.
The bond that joins them together is called a
glycosidic bond.
As the two monosaccharides react and the
glycosidic bond forms, a molecule of water
(H2O) is released.
This type of reaction is known as a
condensation reaction.
Biological Molecules
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• contain 2 monosaccharide units joined by a
glycosidic bond

•Oligosaccharides
• to describe any of the carbohydrates that
contain from 6 to 10 monosaccharide units

•Polysaccharides
• a carbohydrate containing a large number
of monosaccharide units, each joined to the
next by one or more glycosidic bonds
 CARBOHYDRATE
-Disaccharides-

Biological Molecules
 CARBOHYDRATE
-Polysaccharides-

Biological Molecules
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• Maltose
• derives its name
from its presence
in malt, the juice
from sprouted
barley and other
cereal grains
• consists of 2 units
of D-glucopyranose
joined by a glycosidic
acid between carbon
1 of one unit and
carbon 4 of the other
unit
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• Lactose
• principal sugar
present in milk
• consists of D-
galactopyranose
bonded by a
beta-1,4-
glycosidic bond
to carbon 4 of D-
glucopyranose
• reducing sugar
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• Sucrose (table
sugar)
• most
abundant
• obtained
principally from
the juice of
sugar cane and
sugar beets
• nonreducing
sugar
B. DISACCHARIDES and OLIGOSACCHARIDES
•Relative Sweetness
•Fructose
• sweetest – even sweeter than sucrose
• Honey
• D-fructose and D-glucose
•Lactose
•almost no sweetness and is sometimes added
to food as a filler
 Important
Polysaccharides

Biological Molecules
C. POLYSACCHARIDES
•Polysaccharides
•Starch: Amylose and Amylopectin
• used for energy storage in plants
• complete hydrolysis yields only D-Glucose
• Amylose – composed of continuous,
unbranched chains of as many as 4000 D-
glucose units joined by alpha-1,4-glycosidic
bonds
• Amylopectin – contains chains of as many
as 10,000 D-glucose units joined by alpha-
1,4-glycosidic bonds
• new chains of 24-30 units are started by
alpha-1,6-glycosidic bonds
C. POLYSACCHARIDES
•Polysaccharides
•Glycogen
• acts as the energy-reserve carbohydrate for
animals
• it is branched polysaccharide containing
approximately 106 glucose units joined by
alpha-1,4 and alpha-1,6-glycosidic bonds
C. POLYSACCHARIDES
•Polysaccharides
•Cellulose
• most widely distributed plant skeletal
polysaccharide
• is a linear polysaccharide of D-glucose units
joined by beta-1,4-glycosidic bonds
 Important
Polysaccharides

Biological Molecules
 Carbohydrates
Carbohydrates Contain the Elements:

Carbon
Hydrogen
Oxygen
They Are Split Into Three Groups
Known As:

Monosaccharides(Monomers)
Disaccharides(Dimers)
Polsaccharides(Polymers)
CARBOHYDRATES
• means “hydrate of carbon”
• derives from the formula Cn(H O)m 2

• Glucose: C6H12O6 or C6(H2O)6

• most are polyhydroxyaldehydes,

polyhydroxyketones, or compounds that yield
them after hydrolysis
• saccharides – simpler members of the CHO
family (Latin: saccharum – sugar)
• Monosaccharide, Disaccharide, Oligosaccharide,
and Polysaccharide
A. MONOSACCHARIDES
• C6H12O6
• with one of the carbons being the carbonyl
group of either an aldehyde or a ketone

• have 3 to 9 carbon atoms

• -ose indicates that a molecule is a
carbohydrate
• tri-, tetr-, pent-, so and so forth - indicate the
number of carbon atoms in the chain
A. MONOSACCHARIDES

•Aldoses
• monosaccharides
containing an aldehyde
group
A. MONOSACCHARIDES

•Ketoses
• monosaccharides
containing a ketone
group
A. MONOSACCHARIDES

•2 Trioses
• aldotriose
glyceraldehyde

• ketotriose
dihydroxyacetone
A. MONOSACCHARIDES
• D- and L-
Monosaccharides
•D-Monosaccharide
• has the –OH group
on its penultimate
carbon to the right

•L-Monosaccharide
• has the –OH group
on its penultimate
carbon to the left
CONFIGURATIONAL RELATIONSHIPS
AMONG THE ISOMERIC
D-ALDOTETROSES, D-ALDOPENTOSES,
AND D-ALDOHEXOSES
CONFIGURATIONAL RELATIONSHIPS
AMONG
D-2-KETOPENTOSES AND
D-2-KETOHEXOSES
A. MONOSACCHARIDES
•D-
• specifies the configuration
at the stereocenter farthest
from the carbonyl group
•Prefixes (rib-, arabin-,
and gluc-)
• specify the configuration
of all other stereocenters in
the monosaccharide relative
to one another
•-ose
• indicates that the
compound is a carbohydrate
A. MONOSACCHARIDES
•Most Abundant
Hexoses

•D-Glucose
•D-Galactose
• D-aldohexoses
•D-Fructose
• D-ketohexose
A. MONOSACCHARIDES
•Amino Sugars
• a monosaccharide in which an –OH group is
replaced by an –NH2 group
•D-Glucosamine
•D-Mannosamine
•D-Galactosamine
A. MONOSACCHARIDES
•Physical Properties
• are colorless, crystalline solids

•Are very soluble in water

• because hydrogen bonding is possible
between their polar –OH groups and water

•Slightly soluble in ethanol

•Insoluble in nonpolar solvents such as
diethyl ether, dicloromethane, and benzene
A. MONOSACCHARIDES
•Cyclic Structure
• Haworth Projection
•A way to view furanose and pyranose forms
of monosaccharides
•The ring is drawn flat and viewed through its
edge with the anomeric carbon (new C
stereocenter created in forming the cyclic
structure) on the right and the oxygen atom
to the rear
•A 5- or 6-membered cyclic hemiacetal is
represented as a planar pentagon or
hexagon, respectively, lying roughly
perpendicular to the plane of the paper
A. MONOSACCHARIDES
•Cyclic Structure
• Haworth Projection

•β means that the –OH on the anomeric

carbon lies on the same side of the ring as
the terminal –CH2OH

•α means that the –OH on the anomeric

carbon lies on the side of the ring opposite
from the terminal –CH2OH
A. MONOSACCHARIDES
•Cyclic Structure
• Haworth Projection

•-pyran- a 6-membered hemiacetal ring

•-furan- a 5-membered hemiacetal ring
•Pryanose and Furanose
•Are used because monosacharide 5- and
6-membered rings correspond to the
heterocyclic compunds pyran and furan
REACTION OF MONOSACCHARIDES
•Formation of Glycosides (Acetals)
•Acetal – yields when hemiacetal is treated
with one molecule of alcohol

•Glycoside
•A carbohydrate in which the –OH group on
its anomeric carbon is replaced by an –OR
group

•Glycosidic Bond
•the bond from the anomeric carbon of a
glycoside to an –OR group
REACTION OF MONOSACCHARIDES
•Reduction to Alditols
•Carbonyl group is reduced to an hydroxyl
group by a variety of reducing agents,
including hydrogen in the presence of a
transition metal catalyst and sodium
borohydride – alditols

• drop –ose and change to -itol

NaBH4

D-Glucitol
(D-Sorbitol)
Xylitol – used as a
sweetening agent in
“sugarless” products
REACTION OF MONOSACCHARIDES
•Oxidation to
Aldonic Acids
(Reducing
Sugars)

•Aldehyde
group of an
aldose can be
oxidized,
under basic
conditions, to
a carboxylate
group
REACTION OF MONOSACCHARIDES
•Oxidation to
Uronic Acids

•Enzyme-
catalyzed
oxidation of
the primary
alcohol at
carbon 6 of a
hexose yields
a uronic acid
REACTION OF MONOSACCHARIDES
•Phosphoric Esters
•Important in the
metabolism of
monosaccharides

• eg. Conversion
of glucose to
glucose-6-
phosphate
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• contain 2 monosaccharide units joined by a
glycosidic bond

•Oligosaccharides
• to describe any of the carbohydrates that
contain from 6 to 10 monosaccharide units

•Polysaccharides
• a carbohydrate containing a large number
of monosaccharide units, each joined to the
next by one or more glycosidic bonds
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• Sucrose (table
sugar)
• most
abundant
• obtained
principally from
the juice of
sugar cane and
sugar beets
• nonreducing
sugar
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• Lactose
• principal sugar
present in milk
• consists of D-
galactopyranose
bonded by a
beta-1,4-
glycosidic bond
to carbon 4 of D-
glucopyranose
• reducing sugar
B. DISACCHARIDES and OLIGOSACCHARIDES
•Disaccharides
• Maltose
• derives its name
from its presence
in malt, the juice
from sprouted
barley and other
cereal grains
• consists of 2 units
of D-glucopyranose
joined by a glycosidic
acid between carbon
1 of one unit and
carbon 4 of the other
unit
B. DISACCHARIDES and OLIGOSACCHARIDES
•Relative Sweetness
•Fructose
• sweetest – even sweeter than sucrose
• Honey
• D-fructose and D-glucose
•Lactose
•almost no sweetness and is sometimes added
to food as a filler
C. POLYSACCHARIDES
•Polysaccharides
•Starch: Amylose and Amylopectin
• used for energy storage in plants
• complete hydrolysis yields only D-Glucose
• Amylose – composed of continuous,
unbranched chains of as many as 4000 D-
glucose units joined by alpha-1,4-glycosidic
bonds
• Amylopectin – contains chains of as many
as 10,000 D-glucose units joined by alpha-
1,4-glycosidic bonds
• new chains of 24-30 units are started by
alpha-1,6-glycosidic bonds
C. POLYSACCHARIDES
•Polysaccharides
•Glycogen
• acts as the energy-reserve carbohydrate for
animals
• it is branched polysaccharide containing
approximately 106 glucose units joined by
alpha-1,4 and alpha-1,6-glycosidic bonds
C. POLYSACCHARIDES
•Polysaccharides
•Cellulose
• most widely distributed plant skeletal
polysaccharide
• is a linear polysaccharide of D-glucose units
joined by beta-1,4-glycosidic bonds
THANK YOU…