Physical properties of

monosaccharides
1. Aldose-Ketose isomerism
It is the existence of an aldose and a ketose with the same molecular
formula.
Eg. Aldoses and ketoses
2. Stereo isomerism
• The presence of one or more asymmetric carbons in the molecule
may result in the existence of a compound in more than one
structural configuration due to different 3d spatial arrangements of
the groups or atoms held by its asymmetric carbons.
• This is stereo isomerism
3. Optical isomerism
• When ordinary light consisting of rays vibrating in many different
planes, passes through a Nicol prism,the emergent light consists of
rays vibrating in a single plane only, is called plane polarized light
• When polarised light is passed through the solution of a substance
having asymmetric carbon ,the electromagnetic field around the
asymmetric carbon ,not being uniform in all directions due to four
different groups held by that carbon.
• This influences the polarised light unequally and rotates the plane of
its vibration either clockwise or anticlockwise
• Clockwise-dextrorotatory (d),(+), anti-clockwise-levorotatory(l)(-)
4. D-L Stereoisomerism
• The basis of the Classification into D and L isomers is the spatial
orientation of the H and OH groups on the penultimate cabon.
• The asymmetric carbon farthest from the aldehyde or ketonyl carbon
and nearest to the terminal carbon at the other end of the molecule.
• D and L isomers are mirror images of each other.
5. pyranose-furanose isomerism
• Due to the reactivity of the aldehydic or ketonyl group of the molecule
both aldoses and ketoses with 6 or more carbon atoms exist in
tautomeric ring forms.
• Ring is formed by the condensation of the aldehydic or ketonyl group
with an alcoholic OH group of another carbon of that molecule.
• A hemiacetal or a hemi ketal is thus formed in the aldose or ketose
respectively
• Aldehyde or ketone group is changed to an OH group with potential
aldehydic or ketonyl properties
• Carbonyl carbon gets linked by a C-O-C linkage with the alcoholic carbon
6.Epimerism
• If two monosaccharides differ from each other in their configuration
around a single specific carbon atom.
• Galactose- C4 epimer of glucose
• Mannose- C2 epimer of glucose
7. Mutarotation
• The change in specific optical rotation representing the
interconversion of α andβ forms of D-glucose to an equilibrium
mixture.
• α -D -glucose ↔ equilibrium mixture ↔ β-D-glucose
+112.2 ͦ +52.7 ͦ ͦ + 18.7 ͦ
In aqueous solution the β form is more predominant due to its stable
conformation.
The equilibrium mixture contains 63% β-anomer and 36% α-anomer of
glucose with 1% open chain form.
Chemical properties
• 1 .Reactions with strong acids

• When treated with strong acids monosaccharides undergoes

dehydration with an elimination of 3 water molecules.
• Hexoses gives hydroxyl methyl furfurals ,pentoses gives furfurals.
• These furfurals condenses with phenolic (α-naphthol) compounds to
form coloured products.
• This is the basis of Molisch test, Bial’s test, Mucic acid test,Seliwanoffs
test
2. Reaction with alkalies
• Sugars possessing anomeric carbon undergoes tautomerisation in
alkaline solutions.
• Results in the formation of enediols
• Enediols are highly reactive .
• Eg. Glucose in alkaline solution for several hours undergoes
isomerisation to form D-fructose and D-mannose. This reaction is
known as Lobry de Bruyn-von Ekenstein transformation
3.Reducing action
• Reducing property is attributed to free aldehyde or keto group of
anomeric carbon
• This is the basis of Benedicts test ,Fehlings test ,Barfoeds test etc
4.Oxidation
• Oxidation of aldehyde group results in the formation of gluconic acid
• Oxidation of terminal alcoholic group leads to production of
glucuronic acid
• Oxidation of aldehyde and terminal alcoholic group leads to formation
of glucosaccharic acid.
• D-glucuronic acid-it is formed from glucose in liver by uronic acid
pathway.It conjugates toxic substances ,drugs,hormones,bilirubin and
converts them into non toxic glucuronide, which is excreted in urine.
5.Reduction
• Aldehyde or keto group of monosaccharide is reduced to
corresponding alcohol when treated with reducing agents such as
sodium amalgam
• D- Glucose → D- Sorbitol
• D- Galactose → D- Dulcitol
• D- Mannose → D- Mannitol
• D- Fructose → D- Mannitol + D- Sorbitol
• D-Ribose → D-Ribitol
Clinical significance
• Sorbitol &dulcitol: when accumulate in tissues in large amounts
cause strong osmotic effects leads to swelling of cells and conditons
such as cataract,peripheral neuropathy,nephropathy
• Mannitol is useful to reduce intracranial tension by forced diuresis
6.Osazone formation
• Reducing sugars when boiled with phenyl hydrazine in acetic acid
forms osazones

• C1 &C2 are involved in osazone formation.

• Glucose, fructose and mannose gives needle shaped osazones
because they differ in their configuration around C1 &C2 carbon
• Maltose gives sunflower petal shaped crystals and lactose gives
powder- puff crystals.
7.Formation of esters
• Alcoholic groups of monosaccharides are esterified by non-enzymatic
or enzymatic reactions.
• Eg. Glucose-6-phosphate, glucose -1-phosphate
1.Glycosides
• When the hemiacetal or hemiketal hydroxyl group of a carbohydrate
is linked with alcohol group of another compound glycosides are
formed.
• Glycosides possess a carbohydrate and a non-carbohydrate residue in
the same molecule.
• Non-carbohydrate residue is called aglycone.
• Aglycones of glycosides are methyl
alcohol,phenol,hydroquinones,sterols and anthraquinones.
Biomedical importance
• They are found in many drugs, spices,plants and in animal tissues.
• Cardiac glycosides- digitalis,digitonin-used in cardiac insufficiency
• Ouabain- it is sodium pump inhibitor.it inhibits active transport of Na⁺
in the cardiac muscle.it is obtained from Strophanthus spp.
• Phlorhizin –blocks transport of sugar across the mucosal cells of small
intestine and renal tubular epithelium.it is obtained from root and
bark of apple tree.
2. Deoxy sugars

• Sugars in which oxygen of the –OH group is removed leaving the

hydrogen.
• Eg .2-deoxy –D-ribose -found in DNA
• 6-deoxy –L-galactose is found as a constituent of glycoproteins,
blood group substances and bacterial polysaccharides.
3. Amino sugars
• Sugars containing -NH₂ group in their structures are called amino sugars.
• Galactosamine, glucosamine ,mannosamine are examples.
• N-acetyl derivatives of D-glucosamine is a constituent of mucopolysaccharides
such as heparin,hyaluronic acid and blood group substances.
• It is constituent of shells of crustaceae,where it occurs as chitin which is made
of repeating units of N-acetylated glucosamine.
• Galactosamine is also a constituent of MPS
• Antibiotics- Erythromycin, Carbomycin contains amino sugars
4. Amino sugar acids
• Neuraminic acid (pyruvic acid + D-mannosamine) and sialic acid are
found in number of mucopolysaccharides and in gangliosides.
• Certain bacterial cell walls contain muramic acid
• Neuraminidase is the enzyme which hydrolyzes NANA from a
compound.
Glycosaminoglycans(Mucopolysaccharides)

MPS COMPOSITION LOCATION FUNCTIONS

Hyaluronic acid Synovial fluid of joints, Serve as lubricant, shock
vitreous humour of eye, absorber, facilitate cell
loose connective tissue, migration in
and umbilical cord embryogenesis,
morphogenesis, wound
healing
Chondroitin sulfate Sites of calcification in Provide an endoskeletal
bone and structures help to
cartilage ,certain neurons maintain their shape.
Have role in
compressibility of
cartilage in weight
bearing bones.
Keratan sulfate Cornea, loose connective Transparency of cornea
tissue, cartillage
Dermatan sulfate Skin, blood vessels ,heart Transparency of cornea
valves and maintains the overall
shape of the eye
Revision:
1.Define carbohydrates
2. Classification of carbohydrates
3.Aldoses .examples
4. Ketoses . Examples
5.homopolysaccharides.examples
6.heteropolysaccharides.examples
7.Reducing sugars.examples
8.non-reducing sugars .examples
9.Biologically important pentose
10.Components of lactose & linkage
11. Components of maltose & linkage
12.Components of sucrose & linkage
13.Invert sugar
14.Racemic mixture
15.Dextrorotatory sugars
16.Levorotatory sugars
17.Epimers.examples
18.Anomers
19.Mutarotation
20.Reducing property of monosaccharides
21.Oxidation property
22.Benedicts test
23.Clinical significance of sorbitol,mannitol and dulcitol
24.Deoxy sugar
25.Difference between inulin & insulin
26.Dextrin & dextran
27.Linkage in cellulose
28.Cellulose cannot be digested by humans.why
29.Hyaluronic acid linkage
30.Chondroitin sulfate