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CARBOHYDRATESCARBOHYDRATES
Abelgas, Aliza May B.
BS Nursing
general formula is commonly used
to represent many carbohydrates,
which means "watered carbon"
Carbohydrates are the nutritional
category for sugars and molecules
that your body breaks down to make
sugars.
ENERGY SOURCE ENERGY STORAGE CARBON SOURCE
STRUCTURE
OR
PROTECTION
RECOGNITION
OR
SIGNALLING
CAN BE ATTACHED
TO OTHER
MACROMOLECULES
CLASSES OF CARBOHYDRATESCLASSES OF CARBOHYDRATES
MONOSACCHARIDES
DISACCHARIDES
OLIGOSACCHARIDES
POLYSACCHARIDES
Any of the basic compounds that serve as
the building blocks of carbohydrates.
Contain at least three carbons.
SIMPLESIMPLESIMPLE
SUGARSUGARSUGAR
glucose
fructose
galactose
Can be either ALDEHYDES or KETONES;
that is, they are molecules with more
than one hydroxyl group (―OH), and a
carbonyl group (C=O) either at the
terminal carbon atom (aldose) or at
the second carbon atom (ketose).
It is found in fruits and
honey and is the major
free sugar circulating in
the blood of higher
animals.
It is the source of energy
in cell function, and the
regulation of its
metabolism is of great
importance.
Glucose aka dextroseGlucose aka dextrose
SINGLESINGLESINGLE
SUGARSUGARSUGAR
Fructose, along with
glucose, occurs in fruits,
honey, and syrups; it also
occurs in certain
vegetables.
It is a component, along
with glucose, of the
disaccharide sucrose, or
common table sugar.
FructoseFructose
SINGLESINGLESINGLE
SUGARSUGARSUGAR
It is usually found in nature
combined with other sugars.
Galactose is also found in
complex carbohydrates nd in
carbohydrate-containing lipids
called glycolipids, which occur
in the brain and other nervous
tissues of most animals.
Galactose or milk sugarGalactose or milk sugar
SINGLESINGLESINGLE
SUGARSUGARSUGAR
Carbons are numbered from the top.
Most oxidized C goes at top.
Last C will always be part of a CH OH group (not chiral).
Vertical lines go into the page.
Horizontal lines come out of the page.
Crosses can also be the carbons.
Stereochemistry of the last chiral C (2nd to last C in chain)
determines the stereochemisty of the sugar.
D-Isomer: if -OH is to the right.
L-Isomer: if -OH is to the left.
Fisher
Projections
-used to represent carbons.
-shows chiral carbons as the intersection of
vertical and horizontal lines.
rules:
2
D-Glyceraldehyde
L-Glyceraldehyde
Draw the Fischer
projection of the acyclic
form of D-glucose.
1.
Haworth
Projections
-is a common way of writing a structural formula to
represent the cyclic structure of monosaccharides
with a simple three-dimensional perspective
steps:
2. Number the carbon
chain in 1 staring at the
top.
3. To generate the pyranose ring, the oxygen atom
on C-5 in 1 needs to be attached to C-1 by a single
bond.
5. Add the ligands on C-2 through C-5
in 4. The ligands pointing up in 3 are
pointing up in 4; those pointing down
in 3 are pointing down in 4.
7. Add the two
remaining bonds
to C-1 in 6.
Haworth Projections
steps:
4. Redraw the atom chain
along the horizontal axis as
follows.
6. Remove the hydrogen atom and the oxygen
atom on C-1 and the hydrogen atom in the
hydroxy group on C-5 in 5 and connect the two
atoms by a single bond.
8. Attach a hydrogen atom to the
bond pointing up and a hydroxy
group to the bond pointing down
on C-1 in 7.
9. Interchange the hydrogen atom
and the hydroxy group on C-1 in 8.
α anomer or
β anomer
-An anomer is a geometric variation among
carbohydrates. It is a type of epimer in which
we can see an anomeric carbon atom.
Alpha anomer is
the configuration
of a carbohydrate
in which the
hydroxyl group is
cis to the
exocyclic oxygen
at the anomeric
center.
Beta anomer is the
configuration of a
carbohydrate in
which the
hydroxyl group is
trans to the
exocyclic oxygen
at the anomeric
center.
The hydroxyl group in the downward direction
is shown in green color in the above image. The
downward direction resembles the alpha
anomer.
The hydroxyl group in the upward direction is
shown in red color in the above image. The
upward direction resembles the alpha anomer.
oxidation-reduction
Complete oxidation of sugars
supplies energy.
All monosaccharides are reducing
sugars (sugars that can be
oxidized).
Reducing sugars must have a free
ANOMERIC CARBON.
Free anomeric carbon=REDUCING END.
Another oxidation carried out by an
enzyme is DEHYDROGENASE.
Oxidation of Glucose:
The reducing end of a sugar is the end with a
free anomeric hydroxyl group.
esterification
Esters are formed by the reaction
of alcohols (-OH) with acids.
PHOSPHATE ESTER - one of the
most important biological esters.
Performed in cells by transfer of
a phosphoryl group from ATP to a
carbohydrate hydroxyl; catalyzed
by KINASES.
DOUBLEDOUBLEDOUBLE
SUGARSUGARSUGAR
lactose
maltose
sucrose
Any substance that is composed of two
molecules of simple sugars linked to each
other.
Disaccharides are crystalline water-
soluble compounds. The
monosaccharides within them are linked
by a glycosidic bond (or glycosidic
linkage), the position of which may be
designated α- or β- or a combination
of the two (α-,β-).
DOUBLEDOUBLEDOUBLE
SUGARSUGARSUGAR
obtained from sugar cane and
sugar beets.
consists of α-D-glucose and β-D-
fructose.
has an α, β-1,2-glycosidic bond.
not a reducing sugar.
anomeric carbon (C1) on glucose is
linked to the anomeric carbon (C2)
on fructose.
Sucrose or table sugar:Sucrose or table sugar:
DOUBLEDOUBLEDOUBLE
SUGARSUGARSUGAR
Galactose in a β(1→4)
linkage with glucose.
Galactose is converted by the
body to glucose and glucose
used for energy.
Lactose IS digestible by most
humans.
Lactose Intolerance -
deficiency in enzyme lactase.
Lactose or milk sugar:Lactose or milk sugar:
Enzyme LACTASE present in small intestine
hydrolyzes lactose to galactose and glucose.
Maltose or malt sugar:Maltose or malt sugar: DOUBLEDOUBLEDOUBLE
SUGARSUGARSUGAR
formed from two units of
glucose joined with an α(1→4)
bond.
Maltose is the two-unit
member of the amylose
homologous series, the key
structural motif of starch.
found in starchy grains.
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR
Any carbohydrate of from three to six units
of simple sugars.
A large number of oligosaccharides
have been prepared by partially
breaking down more
polysaccharides. Most of the few
naturally occurring
oligosaccharides are found in
plants.
raffinose
stachyose
Is a trisaccharide composed of
galactose, glucose, and fructose.
It can be found in beans, cabbage,
brussels sprouts, broccoli, asparagus,
other vegetables, and whole grains
Procedures concerning
cryopreservation have used raffinose
to provide hypertonicity for cell
desiccation prior to freezing
RaffinoseRaffinose
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR
a tetrasaccharide consisting of two
α-D-galactose units, one α-D-glucose
unit, and one β-D-fructose unit
sequentially linked as
gal(α1→6)gal(α1→6)glc(α1↔2β)fru.
Stachyose occurs naturally in
numerous vegetables (e.g. green
beans, soybeans and other beans) and
other plants.
StachyoseStachyose
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR
influence structure, folding and stability of protein.
may determine the lifetime of a protein.
serve as markers to identify a cell type.
when glycosylated proteins are at the cell surface:
can MODULATE CELL-CELL INTERACTIONS1.
Changes in carbohydrate content may influence contact inhibition
of cells.
2.can MODULATE CELL-MOLECULE INTERACTIONS (e.g. hormone with
receptor)
3.can serve as ANTIGENIC DETERMINANTS
e.g. The difference
between blood
types is due to
glycosylation of
red blood proteins.
presence or absence of the terminal carbohydrate is
genetically determines the blood type.
blood plasma contains antibodies against foreign blood-
group antigens that aggregate the foreign blood cells.
Type A blood has antibodies against that recognize B
sugars.
Type B blood contains antibodies against A sugars.
Type O blood has antibodies against both A and B
sugars(universal donor)
Type AB blood contains neither antibody (universal
acceptor)
influenced by the presence or absence of Rh factor
(blood protein)
incompatible blood types cause
precipitation of RBCs, block blood flow in
organs and can cause death
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR
starch
cellulose
glycogen
The form in which most natural
carbohydrates occur. Polysaccharides are the
most abundant carbohydrate found in food.
They are long chain polymeric
carbohydrates composed of
monosaccharide units bound together
by glycosidic linkages.
Polysaccharides may have a molecular
structure that is either branched or
linear.
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR
found in chloroplasts of plant cells;
especially abundant in potatoes, corn
and wheat.
comprises glucose monomers joined in
α 1,4 linkages. The simplest form of
starch is the linear polymer amylose;
amylopectin is the branched form.
In humans and other animals, starch
from plants is broken down into its
constituent sugar molecules, which
then supply energy to the tissues.
Starch or amylum:Starch or amylum:
consisting of a linear chain of several
hundred to many thousands of β(1→4)
linked D-glucose units.
Cellulose is an important structural
component of the primary cell wall of
green plants, many forms of algae and
the oomycetes.
is the most abundant organic polymer
on Earth.
Other cellulose derivatives are used as
adhesives, explosives, thickening
agents for foods, and in moisture-
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR
CelluloseCellulose
COMPLEXCOMPLEXCOMPLEX
SUGARSUGARSUGAR

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Carbohydrates

  • 2. general formula is commonly used to represent many carbohydrates, which means "watered carbon" Carbohydrates are the nutritional category for sugars and molecules that your body breaks down to make sugars.
  • 3. ENERGY SOURCE ENERGY STORAGE CARBON SOURCE STRUCTURE OR PROTECTION RECOGNITION OR SIGNALLING CAN BE ATTACHED TO OTHER MACROMOLECULES
  • 4. CLASSES OF CARBOHYDRATESCLASSES OF CARBOHYDRATES MONOSACCHARIDES DISACCHARIDES OLIGOSACCHARIDES POLYSACCHARIDES
  • 5. Any of the basic compounds that serve as the building blocks of carbohydrates. Contain at least three carbons. SIMPLESIMPLESIMPLE SUGARSUGARSUGAR glucose fructose galactose Can be either ALDEHYDES or KETONES; that is, they are molecules with more than one hydroxyl group (―OH), and a carbonyl group (C=O) either at the terminal carbon atom (aldose) or at the second carbon atom (ketose).
  • 6. It is found in fruits and honey and is the major free sugar circulating in the blood of higher animals. It is the source of energy in cell function, and the regulation of its metabolism is of great importance. Glucose aka dextroseGlucose aka dextrose SINGLESINGLESINGLE SUGARSUGARSUGAR
  • 7. Fructose, along with glucose, occurs in fruits, honey, and syrups; it also occurs in certain vegetables. It is a component, along with glucose, of the disaccharide sucrose, or common table sugar. FructoseFructose SINGLESINGLESINGLE SUGARSUGARSUGAR
  • 8. It is usually found in nature combined with other sugars. Galactose is also found in complex carbohydrates nd in carbohydrate-containing lipids called glycolipids, which occur in the brain and other nervous tissues of most animals. Galactose or milk sugarGalactose or milk sugar SINGLESINGLESINGLE SUGARSUGARSUGAR
  • 9. Carbons are numbered from the top. Most oxidized C goes at top. Last C will always be part of a CH OH group (not chiral). Vertical lines go into the page. Horizontal lines come out of the page. Crosses can also be the carbons. Stereochemistry of the last chiral C (2nd to last C in chain) determines the stereochemisty of the sugar. D-Isomer: if -OH is to the right. L-Isomer: if -OH is to the left. Fisher Projections -used to represent carbons. -shows chiral carbons as the intersection of vertical and horizontal lines. rules: 2 D-Glyceraldehyde L-Glyceraldehyde
  • 10. Draw the Fischer projection of the acyclic form of D-glucose. 1. Haworth Projections -is a common way of writing a structural formula to represent the cyclic structure of monosaccharides with a simple three-dimensional perspective steps: 2. Number the carbon chain in 1 staring at the top. 3. To generate the pyranose ring, the oxygen atom on C-5 in 1 needs to be attached to C-1 by a single bond.
  • 11. 5. Add the ligands on C-2 through C-5 in 4. The ligands pointing up in 3 are pointing up in 4; those pointing down in 3 are pointing down in 4. 7. Add the two remaining bonds to C-1 in 6. Haworth Projections steps: 4. Redraw the atom chain along the horizontal axis as follows. 6. Remove the hydrogen atom and the oxygen atom on C-1 and the hydrogen atom in the hydroxy group on C-5 in 5 and connect the two atoms by a single bond. 8. Attach a hydrogen atom to the bond pointing up and a hydroxy group to the bond pointing down on C-1 in 7. 9. Interchange the hydrogen atom and the hydroxy group on C-1 in 8.
  • 12. α anomer or β anomer -An anomer is a geometric variation among carbohydrates. It is a type of epimer in which we can see an anomeric carbon atom. Alpha anomer is the configuration of a carbohydrate in which the hydroxyl group is cis to the exocyclic oxygen at the anomeric center. Beta anomer is the configuration of a carbohydrate in which the hydroxyl group is trans to the exocyclic oxygen at the anomeric center. The hydroxyl group in the downward direction is shown in green color in the above image. The downward direction resembles the alpha anomer. The hydroxyl group in the upward direction is shown in red color in the above image. The upward direction resembles the alpha anomer.
  • 13. oxidation-reduction Complete oxidation of sugars supplies energy. All monosaccharides are reducing sugars (sugars that can be oxidized). Reducing sugars must have a free ANOMERIC CARBON. Free anomeric carbon=REDUCING END. Another oxidation carried out by an enzyme is DEHYDROGENASE. Oxidation of Glucose: The reducing end of a sugar is the end with a free anomeric hydroxyl group.
  • 14. esterification Esters are formed by the reaction of alcohols (-OH) with acids. PHOSPHATE ESTER - one of the most important biological esters. Performed in cells by transfer of a phosphoryl group from ATP to a carbohydrate hydroxyl; catalyzed by KINASES.
  • 15. DOUBLEDOUBLEDOUBLE SUGARSUGARSUGAR lactose maltose sucrose Any substance that is composed of two molecules of simple sugars linked to each other. Disaccharides are crystalline water- soluble compounds. The monosaccharides within them are linked by a glycosidic bond (or glycosidic linkage), the position of which may be designated α- or β- or a combination of the two (α-,β-).
  • 16. DOUBLEDOUBLEDOUBLE SUGARSUGARSUGAR obtained from sugar cane and sugar beets. consists of α-D-glucose and β-D- fructose. has an α, β-1,2-glycosidic bond. not a reducing sugar. anomeric carbon (C1) on glucose is linked to the anomeric carbon (C2) on fructose. Sucrose or table sugar:Sucrose or table sugar:
  • 17. DOUBLEDOUBLEDOUBLE SUGARSUGARSUGAR Galactose in a β(1→4) linkage with glucose. Galactose is converted by the body to glucose and glucose used for energy. Lactose IS digestible by most humans. Lactose Intolerance - deficiency in enzyme lactase. Lactose or milk sugar:Lactose or milk sugar: Enzyme LACTASE present in small intestine hydrolyzes lactose to galactose and glucose.
  • 18. Maltose or malt sugar:Maltose or malt sugar: DOUBLEDOUBLEDOUBLE SUGARSUGARSUGAR formed from two units of glucose joined with an α(1→4) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. found in starchy grains.
  • 19. COMPLEXCOMPLEXCOMPLEX SUGARSUGARSUGAR Any carbohydrate of from three to six units of simple sugars. A large number of oligosaccharides have been prepared by partially breaking down more polysaccharides. Most of the few naturally occurring oligosaccharides are found in plants. raffinose stachyose
  • 20. Is a trisaccharide composed of galactose, glucose, and fructose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains Procedures concerning cryopreservation have used raffinose to provide hypertonicity for cell desiccation prior to freezing RaffinoseRaffinose COMPLEXCOMPLEXCOMPLEX SUGARSUGARSUGAR
  • 21. a tetrasaccharide consisting of two α-D-galactose units, one α-D-glucose unit, and one β-D-fructose unit sequentially linked as gal(α1→6)gal(α1→6)glc(α1↔2β)fru. Stachyose occurs naturally in numerous vegetables (e.g. green beans, soybeans and other beans) and other plants. StachyoseStachyose COMPLEXCOMPLEXCOMPLEX SUGARSUGARSUGAR
  • 22. influence structure, folding and stability of protein. may determine the lifetime of a protein. serve as markers to identify a cell type. when glycosylated proteins are at the cell surface: can MODULATE CELL-CELL INTERACTIONS1. Changes in carbohydrate content may influence contact inhibition of cells. 2.can MODULATE CELL-MOLECULE INTERACTIONS (e.g. hormone with receptor) 3.can serve as ANTIGENIC DETERMINANTS
  • 23. e.g. The difference between blood types is due to glycosylation of red blood proteins.
  • 24. presence or absence of the terminal carbohydrate is genetically determines the blood type. blood plasma contains antibodies against foreign blood- group antigens that aggregate the foreign blood cells. Type A blood has antibodies against that recognize B sugars. Type B blood contains antibodies against A sugars. Type O blood has antibodies against both A and B sugars(universal donor) Type AB blood contains neither antibody (universal acceptor) influenced by the presence or absence of Rh factor (blood protein) incompatible blood types cause precipitation of RBCs, block blood flow in organs and can cause death
  • 25. COMPLEXCOMPLEXCOMPLEX SUGARSUGARSUGAR starch cellulose glycogen The form in which most natural carbohydrates occur. Polysaccharides are the most abundant carbohydrate found in food. They are long chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. Polysaccharides may have a molecular structure that is either branched or linear.
  • 26. COMPLEXCOMPLEXCOMPLEX SUGARSUGARSUGAR found in chloroplasts of plant cells; especially abundant in potatoes, corn and wheat. comprises glucose monomers joined in α 1,4 linkages. The simplest form of starch is the linear polymer amylose; amylopectin is the branched form. In humans and other animals, starch from plants is broken down into its constituent sugar molecules, which then supply energy to the tissues. Starch or amylum:Starch or amylum:
  • 27. consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall of green plants, many forms of algae and the oomycetes. is the most abundant organic polymer on Earth. Other cellulose derivatives are used as adhesives, explosives, thickening agents for foods, and in moisture- COMPLEXCOMPLEXCOMPLEX SUGARSUGARSUGAR CelluloseCellulose