Carbohydrates o Monosaccharides : single (1) • General formula : CnH2nOn or Cn(H2O)n

• Most abundant organic compounds in polyhydroxyaldehyde or where n varies from 3 to 8

the plant world polyhydroxyketone (Glucose and • Prefixes : tri-, tetr-, pent-, …
• “hydrate of carbon” Fructose) • Aldose : monosaccharide containing
• Carbohydrate “markers” on cell surfaces aldehyde group
play key roles in cell-cell recogni<on o Disaccharides : Two (2) • Ketose : monosaccharide containing
process monosaccharide units connected by ketone group
• Produced by photosynthe<c ac<vity of covalent bond (Sucrose and Lactose)
green plants o Oligosaccharides : 2-10
• Provide chemical energy (glucose, monosaccharide units connected by
starch, glycogen) covalent bond (raffinose and
• Components of suppor<ve structure in stachyose)
plants (cellulose), crustacean cells o Polysaccharides : tens of thousands
(chi<n), and connec<ve <ssues in of monosaccharide units connected
animals (acidic polysaccharides) by covalent bond (chi<n and
• Essen<al components of nucleic acids cellulose)
(D-ribose and 2-deoxy-D-ribose) o Hybrid Carbohydrates : Name Formula
• Derives from the formula Cn(H2O)m Carbohydrates with other Triose C 3 H6 O 3
o Glucose (blood sugar) : C6H12O6, can biomolecules Tetrose C 4 H8 O 4
be wriJen as C6(H2O)6 o Derived Carbohydrates : modified Pentose C5H10O5
o Sucrose (table sugar) : C12H22O11, can carbohydrates through reac<ons Hexose C6H12O6
be wriJen as C12(H2O)11 (sorbitol) Heptose C7H14O7
• Polyhydroxyaldehyde or Octose C8H16O8
polyhydroxyketone, or compunds that Monosaccharides
yield them aLer hydrolysis • Single sugar molecule
• Only two trioses : glyceraldehyde and
• Simpler members of carbohydrates : • Carbohydrate that cannot be hydrolyzed dihydroxyketone
Saccharides (sweet taste) to a simpler carbohydrate
• Classified depending on the number of • Classified by their number of carbon
simple sugars they contain atoms

• Glyceraldehyde : Simplest aldotriose
with a stereocenter and exist as a pair of
enan<omer.
• Fischer Projec<on – two dimensional
representa<ons for showing the
configura<on of carbohydrates
(tetrahedral stereocenters)
o Horizontal Lines : Bonds projec<ng
forward
o Ver<cal Lines : Bonds projec<ng to
the rear
o Stereocenter : The only one on the
plane
• Most common D-hexoses are :
• Emil Fischer : Arbitrary assignments of
D- and L- to the enan<omers of
glyceraldehyde (1891)
o D-monosaccharide : -OH on its
penul<mate carbon is on the right in
a Fischer projec<on
o L-monosaccharide : -OH on its
penul<mate carbon is on the leL in
a Fischer projec<on
Important Monosaccharides
• Most common D-tetroses and D-
pentoses are :
o Ribose and Deoxyribose : present as
intermediates in metabolic pathway
and are important building blocks of
RNA and DNA
o D-Glucose
- Known as dextrose
- 5% (m/v) is used as IV source of
nourishment for pa<ents
- Found in our blood
o D-Fructose
- Same formula as D-glucose
(C6H12O6) but is a ketohexose
- Sweetest of the carbohydrates
(twice as sweet as table
sugar/sucrose)
o D-Galactose
- 6-carbon aldohexose
- Found in disaccharide lactose
(milk sugar)
- Found in milk and dairy products
- Galactosemia : When a person is
missing an enzyme that converts
D-galactose to D-glucose, D-
galactose accumulates in the
blood and <ssue
o D-Glucose
- Found in bacteria, fungi, and
plants
 - Five membered cyclic form
Biologically Important Monosaccharides
• Glucose
- Most abundant in nature
- Nutri<onally most important
- Grape fruit good source of glucose
(20-30% by mass) also named as
grape sugar, dextrose, and blood
sugar
- Six membered cyclic form • Galactose
- A component of milk sugar
- Synthesized in human Amino Sugars
- Also called brain sugar (part of the • Carbohydrates that contains -NH2
brain and nerve <ssue) (amino) group insead of an -OH
- Used to differen<ate blood types (hydroxyl) group
- Six membered cyclic form • Only three amino sugars are common in
- Galactosemia : gene<c deficiency in nature : D-Glucosamine, D-
infants Mannosamine, D-Galactosamine
• In naturally occurring amino sugarsk the
carbon 2 hydroxyl group is replaced by
• Fructose an amino group
- Ketohexose
- Sweetes of all sugars; the fruit sugar
- Found in many fruits and in honey
- Good dietary sugar due to higher
sweetness
- Five membered cyclic form • Ribose
- Part of RNA (Ribonucleic acid)
- Part of ATP (Adenosine Triphosphate)
- Part of DNA (Deoxyribonucleic acid)
CHARACTERISTIC REACTIONS OF ALDEHYDES
AND KETONES
• Addi<on of Alcohols : Forma<on of
Hemiacetal
- Hemiacetals are generally unstable
except in cyclic hemiacetal form

• D-Glucose forms these cyclic

Cyclic Forms of Monosaccharides (Haworth
Projec<ons)
• Haworth Projec<ons
- Common way of the cyclic structure
of monosaccharides
- Sir Walter N. Haworth
- Anomeric carbon : New carbon
stereocenter created in forming the
cyclic structure
- Anomers : Stereoisomers that differ in
configura<on only at the anomeric
carbon
- The anomeric carbon of an aldose is
C1; that of the most common ketoses
is C2
monosaccharides
• ß : -OH on the anomeric carbon is one
the same side of the ring as terminal
CH2OH
• ɑ : -OH on the anomeric carbon is on the
opposite side of the ring as the terminal
CH2OH
• Furanose : five-membered cyclic
hemiacetal form of a monosaccharide
• Pyranose : six-membered cyclic
hemiacetal form of a monosaccharide
 Cyclic Forms of Monosaccharides (Chair
Conforma<on)
• For pyranoses, the six-membered ring is
more accurately represented as chair
conforma<on

• Aldopentoses : also form cyclic

hemiacetals
• The most prevalent forms of D-ribose
and other pentoses in the biological
world are furanoses
Cyclic Forms of Monosaccharide
(Mutorota<on)
• Mutorota<on
- Change in specific rota<on that
accompanies the equilibrium of ɑ-
and ß-anomers in aqueous solu<on
• The prefix deoxy- means “without - Common to all carbohydrates that
oxygen” exist in hemiacetal forms
• D-Fructose (2-ketohexose) also forms a
five-membered cyclic hemiacetal
Physical Proper<es of Monosaccharides
• Colorless crystalline solids, very soluble
in water, but only slightly soluble in
ethanol
CHARACTERISTIC REACTIONS OF
MONOSACCHARIDES
• Forma<on of Glycosides : Reac<on with
alcohols
- Monosaccharides in cyclic hemiacetal
conforma<ons reacts with alcohol to
form acetals
- Glycoside : cyclic acetal derived from
a monosaccharide
- Glycosidic bond : bond from anomeric
carbon to the -OR group
- Mutorota<on is not possible
- Glycosides are stable in water and
aqueous base
- Glycosides can be hydrolyzed in
aqueous acid to an alcohol and a
monosaccharide
 • Forma<on of Aldonic Acid : Oxida<on of
Monosaccharides
- Aldehyde group of aldoses is oxidized
under basic condi<on to a carboxylate
group
- Carbohydrates that reacts with an
• Forma<on of Alditols : Reduc<on of oxidizing agent to form aldonic acid is • Forma<on of Phosphate Esters :
Monosaccharides classified as reducing sugar Phosphoric acid reacts with
- Carbonyl group of monosaccharides monosaccharides
are reduced to hydroxyl group using - Phosphate esters are intermediates in
reducing agents (NaBH4, and H2 with the metabolism of monosaccharides
transi<on metal catalyst)
- Alditols : reduc<on of products

• Forma<on of Uronic Acid : Oxida<on of

Monosaccharides
- Sorbitol : Found in berries, cherries,
plums, pears, apples, seaweed, and
algae. 60% as sweet as sucrose and is
used as sugar subs<tute
- Three alditols also common in the
biological world
- Oxida<on of sugars in nature is
catalyzed by enzymes
- Enzyme catalyzed oxida<on of Disaccharides
primary alcohols at C6 of hexoses
- D-glucose yields D-glucuronic acid
that is widely distributed in plants
and animal world. It serves as a
component of the acidic
polysaccharides of connec<ve <ssues
• Contain two monosaccharide units
joined by a glycosidic bond
• Sucrose
- Composed of Glucose and Fructose
- Table sugar
- Most abundant disaccharide in the
biological world
- Obtained from sugar cane and sugar
beets
- Non-reducing sugar
 • Maltose Polysaccharides
- Composed of Glucose and Glucose • Carbohydrates containing a large
- Present in Malt, Juice of sprouted number of monosaccharide units, each
barley and other cereal grains joined to the next by one or more
- Reducing sugar glycosidic bonds
• Starch : Polymer of Glucose
- Used for storage in plants
- Found in all plant seeds and tubers
and is the form in which glucose is
stored for later use
- Can be separated into Amylopec<n
and Amylose
• Lactose
- Composed of Glucose and Galactose
- Principal sugar in milk
- 5%-8% in Human milk
- 4%-6% in cow milk
- Reducing Sugar
• Cellulobiose
- Same with maltose but connected by
ß-Glucosidic linkage
- Amylose : unbranched chains up to
4000 D-Glucose joined by ɑ-1,4-
glycosidic bond
- Amylopec<n : unbranched chains up
to 10000 D-Glucose join by ɑ-1,4-
glycosidic bond; at branching points,
new chains of 24 to 30 units of
glucose 1,6-glycosic bond

• Glycogen : Polymer of Glucose
- Energy-reserve carbohydrate of
animals
- Glycogen is more highly branched
then amylopec<n, with branch points
occuring every 10–15 residues
- Branched polysaccharide of
approximately 106 glucose units
joined by α-1,4- and α-1,6-glycosidic
bond
- Well-nourished adult human has
about 350 g of glycogen in liver and
muscle.
• Cellulose : Polymer of Glucose
- The most widely distributed plant
skeletal polysaccharide, cons<tutes
almost half of the cell-wall material of
wood.
- CoJon is almost pure cellulose.
- Average molecular weight of 400,000
g/mol; approximately 2200 glucose
units per molecule
- Cellulose molecules act like s<ff rods
and align themselves side by side into
well-organized water-insoluble fibers
in which -OH groups form numerous
intermolecular hydrogen bonds
- This arrangement of parallel chains in
bundles give cellulose fibers their
mechanical strength
- Human and other animals cannot
digest cellulose due to absence of
ß-glucosidase (The enzyme that
degrades or breaks down cellulose
into glucose
- Humans only have ɑ-glucosidase that
degrades/breakdowns starch and
glycogen
- Bacteria and microorganism has
ß-glucosidase
- Termites have such bacteria in their
intes<nes and use wood as their
principal food
- Ruminants (cud chewing animals) and
horse can also digest grasses and hay
Acidic Polysaccharides : Polymer containing
sugar acids
• Group of polysaccharides that contain
carboxyl groups and/or sulfuric ester
groups, and play important role in the
structure and func<on of connec<ve
<ssues
• No single general type of connec<ve
<ssue
• A large number of highly specialized
form exist (car<lage, bone, synovial fluid,
skin, tendons, blood vessel,
intervertebral disk, and cornea
• Most connec<ve <ssues are made up of
collagen, a structural protein, in
combina<on with a variety of acidic
polysaccharides
• Hyaluronic Acid : Polymer of Glucuronic - Binds with an<thrombin III, a plasma
Acid and N-Acetylglucosamine protein, involved in termina<ng the
- Simplest acidic polysaccharide closng process
present in connec<ve <ssue
- Contains 300 to 100,000 repea<ng
units
- Most abundant in embryonic <ssue
and in specialized connec<ve <ssues
(synovial fluid lubricant of joints in
the body and vitreous of the eye)

• Heparin : Polymer of Glucuronic Acid

and Glucosamine

- An<coagulant in blood (inhibits blood

clot forma<on)
- Used in open-heart surgery
- Synthesized and stored in mast cells
of various <ssues (liver, lungs, and
gut)