Carbohydrate, class of naturally occurring compounds and derivatives formed from them. In the early part of the 19th century, substances such as wood, starch, and linen were found to be composed mainly of molecules containing atoms of carbon (C), hydrogen (H), and oxygen (O).
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
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
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