CARBOHYDRATES 2 4.

HEXOSES
BIOMEDICAL IMPORTANCE MONOSACCHARIDE
a. D-Glocose
1.TRIOSES
 Beta-d glucose is the most abundant in nature
 D-Glyceraldehyde and Dihydroxyacetone and the most important for from a human
 Two trioses that are important intermediates in nutritional standpoint
the process of glycolysis, a series of reaction  D-glucose taste sweet is nutritious and is an
whereby glucose is converted into two important component of human diet.
molecules of pyruvate.  L glucose is tasteless and other body cannot use
 D-Glyceraldehyde is a chiral molecule but it
Dihydroxyacetone is not.  Ripe fruit particularly grapes (20% to 30%
 There are precursors of glycerol, which the glucose )is referred to as a grape sugar
organism synthesizes and incorporates into  Also known as dextrose, which draws attention
various type of lipids. to the fact that the optically active D-glucose, in
aqueous solution, rotates plane-polarized light
2. TETROSES
to the right.
 Erythrose is an intermediate in  Converted into glycogen for storage into liver
hexosemonophosphate shunt which is an and muscles.
alternative pathway of glucose oxidation  Dextran a polymer of D-glucose is used as a
plasma expander to increase blood volume in
3.PENTOSES case of hemorrhage and shock.
a. D-ribose b. D-galactose
 a constituent of RNA: constituent of certain  constituent of milk sugar lactose and also in
coenzymes FAD ( flavin adenine dinucleotide), tissues as a constituent of Galactolipid and
NAD ( nicotinamide adenine dinucleotide) glycoprotein.
b. D-2-deoxyribose  An epimer of glucose (carbon 4). it is formed in
the body from glucose by Epimerization by the
 a constituent of DNA. enzyme epimerase in the liver.
C. L-xylulose  Less sweet than glucose and less soluble in
water.
 A metabolite of d-glucoronic acid and is  On oxidation with hot nitric acid, it yields
excreted in urine of humans afflicted with dicarboxylic acid, mucic acid, which helps in its
hereditary abnormality in metabolism called identification, since the crystals of mucic acid
pentosuria . are not difficult to produce and have
d. D-Xylose characteristic shape.

 Known as wood sugar and use as diagnostic aid

for cystic fibrosis

Source: corn cobs.

e. L-fucose ( methylpentose)

 occurs in glycoprotein.
C. Fructose

 “Fruit sugar” as it occurs free and fruits.

 Very sweet sugar, much sweeter than sucrose
and more reactive than glucose.
 Occurs as constituent of sucrose and
polysaccharides inulin.
 Exhibit mutarotation.
 Biomedical importance: Seminole fluid in rich in
fructose and sperms, utilize fructose for energy.
Fructose is formed in the seminiferous tabular
epithelial cell from glucose.
2. Amino Sugars (Hexosamines)
 Containing -NH2
 they gives chemical reaction characteristic
of sugar.

 Amino sugars occur combined as N-acetyl

derivatives.
d. D-Mannose

 Does not occur free in nature but is in

combination with the polysaccharide.
 In the body it is found as a constitute of
glycoprotein.

a.N-acetyl derivative of d-glucosamine

 Constituent of MPS (mucopolysaccharide)

Other medical important derivatives
monosaccharides
1. Deoxy Sugar
 Sugars in which the oxygen of an -OH group has
been removed, leaving the hydrogen. Thus, -
CHOH or -Ch2OH becomes -CH2 or -CH3.
 -2-deoxy ribose (DNA) and 6-deoxy-L-galactose
as a constituent of glycoprotein, blood group
substances and bacterial polysaccharides.
 Present in hyaluronic acid and heparin and also
in blood group substances;
of
 Constituent of chitin (also called ‘chitosamine”)
N-acetyl-galactosamine
 Found in sulphated MPS as chondroitin
sulphates which are present in cartilage, bone,
tendons and heart valves ( known as
“Chondrosamine”)
Antibiotics
 Erythromycin contains dimethyl amino sugar
and carbomycin 3-amino-D-ribose. Amino sugar
are related to the antibiotics activity of these
drugs.
3. Sialic Acid REACTIONS OF MONOSACCHARIDES
 Neuraminic Acid: an idol condensation product
1. Reaction of sugars due to carbinol group.
of pyruvic acid and D-mannosamine; unstable
A) Formation of phosphate ester and sugar.
and found in the nature in the form of acylated
derivatives known as sialic acid (N-acetyl Phosphorylation is formation of sugar phosphate and
neuraminic acid – NANA) their derivatives.
 Muramic acid: condensation product of D-
Kinase - are enzymes that catalyzes the transfer of
glucosamine and lactic acid
phosphate from ATP to their substance.
 Neuraminic acid and sialic acids occur in a
number of mucopolysaccharides and in Formation of phosphate Ester to alcohols
glycolipids like gangliosides.
 Nitrogenous oligosaccharides containing  Phosphate ester of alcohol contain a -PO3-²
neurominic acid are found in milk. group bonded to the oxygen atom of an -OH
 Certain bacterial cell walls contain “muramic group.
acid”.  The -OH groups of sugars can add -PO3-² groups
 Neuraminidase Is the enzyme which hydrolyzes the form phosphate esters in the same manner.
to split N-Acetylneuraminic acid (NANA) from  Phosphate ester of monosaccharides appear as
compound. reactants and products throughout the
metabolism of carbohydrates.
4. Glycosides
 Are compounds containing a carbohydrate and
none carbohydrates (aglycone) residue in the
same molecule. They are named according to
the carbohydrate it contains (e.g. glucoside,
galactoside)
 Glycosides are found in many drugs, spices and
in the constituents of animal tissues. They are
widely distributed in plant kingdom.
 Cardiac glycosides: used in cardiac insufficiency; Sugar phosphates
they are a derivative of digitalis, strophanthus
 Our outstanding biological importance.
and squill plants.
 Phosphate derivatives of monosaccharides are
 Ouabain: inhibits active transport of sodium
found in the living cells, in which they serve as
ions in cardiac muscle in vivo (“sodium pump”
important intermediate in carbohydrates
inhibitor)
metabolism.
 Phlorhizin: from the root and bark of apple
tree; blocks the transport of sugar across the
mucosal cells of small intestine and also renal
tubular epithelium; it displaces sodium ion from
the binding site of ‘carrier protein” and
prevents any binding of sugar molecule, and
produces glycosuria.
 Other glycosides include antibiotics like a
streptomycin.
 B) Formation of Glycosides
 Occur when the -OH group off the numeric
carbon is linked to an alcohol or phenol group.
 Linked by glycosidic bond
 Has two part the glycane and aglycone part

Osazones test - used to differentiate the various sugar.

give a yellow crystalline compound.

o Oxidation to form or produced sugar acid

+Aldonic acid

 When the aldehyde function of an aldose is

oxidized to a carboxylic acid.

C) Dehydration to form Furfural

 Monosaccharides are relatively stable in dilute
acid, but treatment with strong acid results in
loss of water and the formation of furfural.
 Compound is very reactive and reacts with a
number of phenolic and organic aromatic
reagent to produce complex colored products.
 Bases of Molisch test and seliwanoff’s test.

+Uronic Acid

 Are a class of sugar acids with both carbonyl

and carboxylic acid functional groups. They are
sugar is in which the terminal carbon’s hydroxyl
group has been oxidized to a carboxylic acid.

Importance of Uronic acid

 component of structural polysaccharides

 important in detoxication reaction or
D) Reaction due to the Carbonyl Group
conjugation reaction in our body.

o Reaction with Phenylhydrazine the form Osazones

 sugar containing potentially free carbonyl group
Aldaric or Saccharic Acid
from osazones when heated with a mixture of
sodium acetate and excess phenylhydrazine  If both Ends of an aldose chain are oxidized to
reagent. carboxylic acids
 The reaction involves only the carbonyl carbon  These sugars are sometimes useful for the
and the next adjacent carbon. identification of sugars, but they have no
biological significance.
  Usually use alkaline cupric solution which sugar
is oxidized to aldonic and cupric ion are reduced
to cuprous ion.
 Principle in Fehling’s test, Benedict’s test and
Barfoed test.

Ascorbic acid
 Known as vitamin C and derivative of hexonic
acid
 Cannot synthesized in our body.
 Present in large amount in citrus fruits and
tomatoes p
 Deficiency of this can cause scurvy
Fermentation of Sugar

C. Reduction to form sugar alcohols

 Aldoses and ketoses may be reduced to the

corresponding polyhydroxy alcohols.
 Two sugar form from fructos: Glucitol and
Mannito
 Most common sugar alcohols:
+ glucose= Sorbitol (Glucitol)
-use as a sweetener used to relieve occasional
constipation and irregularity.
+ Galactose= Dulcitol (Galactitol)
-the cause of cataract in infants suffering from
galactosemia. it crystallizes and accumulates in  Fermentation is a decomposition of organism
the lens of the eye infant. substance usually a carbohydrates, produce by
+ Mannose =Mannitol the enzymes of a living organism.
-use as Osmotic Diuretic and in Early phase of  Alcohol and carbon dioxide represents the main
oliguria. end product.

Reducing action of sugars

 Sugar containing a potentially free aldehyde or

ketone group is capable of reducing certain
oxidizing agent