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CLASSIFICATION OF CARBOHYDRATES
General Formula: CnH2nOn or Cn(H2O)n
Hydrate of carbon
Definition: A polyhydroxy aldehyde, a polyhydroxy
ketone, or a compound that yields polyhydroxy
aldehydes
or
polyhydroxy
ketones
upon
hydrolysis.
o Glucose - polyhydroxy aldehyde
o Fructose - polyhydroxy ketone
The two examples structures are representative of
all simple carbohydrates.
o Notable feature: There is a presence of a
functional group on each carbon atom
present.
Monosaccharides
A carbohydrate that contains a single polyhydroxy
aldehyde or polyhydroxy ketone unit
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
Disaccharide
A carbohydrate that contains two monosaccharide
units covalently bonded to each other
They are also crystalline, water-soluble.
o Examples: Sucrose (table sugar) and
Lactose (milk sugar)
Hydrolysis of a disaccharide produces two
monosaccharide units.
Oligosaccharide
A carbohydrate that contains three to ten
monosaccharide units covalently bonded to each
other
o Free
oligosaccharides
are
seldom
encountered in biochemical systems.
Found associated with proteins and lipids
Complete hydrolysis: Several monosaccharide
units
Polysaccharide
A polymeric carbohydrate that contains many
monosaccharide units covalently bonded to each
other.
o Number varies from a few hundred to over
50,000 units.
Undergoes
hydrolysis
under
appropriate
conditions to produce monosaccharide.
o Examples: Cellulose and Starch
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
D-Ribose
o Component of a variety of complex
molecules
Two of which are the RNA and the ATP
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
DISACCHARIDES
A carbohydrate in which two monosaccharides are
bonded together.
Formed by reaction a cyclic form of a
monosaccharide with an alcohol (as seen in
glycoside formation).
o Monosaccharide
will
function
as
a
hemiacetal while the other monosaccharide
will function as an alcohol, forming a
disaccharide, the glycoside.
The bond that links the two monosaccharides
together is called a glycosidic linkage.
o Glycosidic linkage the bond between two
monosaccharides resulting from the reaction
between the hemiacetal carbon atom OH
group of one monosaccharide and an OH
group on the other monosaccharide.
Maltose
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
Cellobiose
Produced as an intermediate in the hydrolysis of
the polysaccharide cellulose.
Made up of two D-glucose units
o One must be a beta-D-glucose
o Link is called a beta-(1,4)-linkage because
the OH which are connected are from
Carbon 1 and Carbon 4.
Hydrolysis of cellobiose in acidic condition or in a
cellobiase catalyst
o D-Cellobiose + H2O 2 D-glucose
o Cellobiase will break the beta-(1,4)-linkage
Lactose
Milk sugar (found in milk)
Made up of a beta-D-galactose unit and any Dglucose unit
o Link is a beta-(1,4) glysosidic linkage
Formation of lactose in mammary glands
o Uptake of glucose in bloodstream.
o Glucose will under go epimerization to
yielding galactose, and then the beta-(1,4)
Sucrose
Table sugar
Most abundant disaccharides in the plant
kingdom.
Made up to alpha-D-glucose and beta-D-fructose
o Link is called an alpha, beta-(1-2) glycosidic
linkage. Link is formed in the carbon one of
glucose and carbon 2 of fructose.
Nonreducing sugar
Hydrolysis of Sucrose in acidic condition or in a
surcase catalyst
o D-Sucrose + H2O D-glucose + D-fructose
o Sucrase will break the alpha, beta-(1-2)
glycosidic linkage.
o Both D-glucose and D-fructose are invert
sugars.
Read about Other Types of Glycosidic Linkages
OLIGOSACCHARIDES
Carbohydrates that contain three to ten
monosaccharide units bonded to each other via
glycosidic linkages.
Human lacks digestive enzyme to break the
oligosaccharides,
hence
they
will
remain
undigested.
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
6
unbranched-chain
glucose
polymer
Linked
by
alpha-(1,4)
glycosidic
linkages
300-500 monomers are present
Stable in helical arrangement formed
by twisting the flexible glucose chain.
o Amylopectin branched glucose polymer
Branch occurs once every 25-30
glucose units
Linked
by
alpha-(1,4)
glycosidic
linkages in the linear part and alpha(1,6) glycosidic linkages in the
branched part
100,000 monomers may be present
Iodine test is carried out to test the presence of
starch in solution.
o (+): dark blue-black color.
Glycogen
A polysaccharide containing only glucose units.
Glucose storage polysaccharide in humans and
animals
Has the same function with that of the plants,
hence referred to as animal starch.
Linked by both alpha-(1,4) glycosidic linkages in
the linear part and alpha-(1,6) glycosidic linkages
Starch
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
STRUCTURAL POLYSACCHARIDES
A polysaccharide that serves as a structural
element in plant cell walls and animal
exoskeletons
Two
of
the
most
important
structural
polysaccharides:
o Cellulose
and
Chitin,
both
homopolysaccharides
Cellulose
The structural component of plant cell walls, most
abundant naturally occurring polysaccharide.
Woody portion of plants
An unbranched glucose polymer
o Linked by beta-(1,4) glycosidic linkages
o Linear structure rather than spiral-like
structure in amylose
Water-insoluble due to linearity
Contains 5,000 glucose units.
o Cotton is 95% cellulose
Humans cannot digest cellulose because we lack
enzymes to break beta-(1,4) glycosidic linkages.
Chitin
Second most
polysaccharide.
abundant
naturally
occurring
ACIDIC POLYSACCHARIDES
A polysaccharide with a disaccharide repeating
unit in which one of the disaccharide components
is an amino sugar and one or both disaccharide
components has a negative charge due to a
sulfate group or a carboxyl group.
These are heteropolysaccharides.
o Two different monosaccharides are present
in an alternating pattern.
Hyaluronic Acid
Contains alternating residues of N-aceytl-beta-Dglucosamine (NAG) and D-glucuronate.
o D-glucuronate is formed when D-glucoronic
aid loses its acidic hydrogen atom.
Product obtained when the CH2OH
group of a glucose is oxidized to a
COOH group
Linked by alternating beta-(1,3) and beta-(1,4)
glycosidic linkages.
Heparin
A small highly sulfated polysaccharide with only
15-90 disaccharide residues per chain.
Monosaccharides
present
in
heparin;s
disaccharide repeaing unit are a sulfate dericatice
of D-gluuronate and a doubly sulfated derivative
of D-glucosamine. Both of these monosaccharide
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.
Stoker, H.S. (2016). General, Organic, and Biological Chemistry: Seventh Edition. Cengage:USA.