General characteristics

the term carbohydrate is derived from the

french: hydrate de carbone
compounds composed of C, H, and O
(CH2O)n when n = 5 then C5H10O5
not all carbohydrates have this empirical
formula: deoxysugars, aminosugars
carbohydrates are the most abundant
compounds found in nature (cellulose: 100
billion tons annually)
 General characteristics
Most carbohydrates are found naturally in
bound form rather than as simple sugars
Polysaccharides (starch, cellulose, inulin, gums)
Glycoproteins and proteoglycans (hormones, blood group
substances, antibodies)
Glycolipids (cerebrosides, gangliosides)
Glycosides
Mucopolysaccharides (hyaluronic acid)
Nucleic acids
 Functions
sources of energy
intermediates in the biosynthesis of other basic
biochemical entities (fats and proteins)
associated with other entities such as glycosides,
vitamins and antibiotics)
form structural tissues in plants and in
microorganisms (cellulose, lignin, murein)
participate in biological transport, cell-cell
recognition, activation of growth factors,
modulation of the immune system
Classification of carbohydrates
Monosaccharides (monoses or glycoses)
Trioses, tetroses, pentoses, hexoses
Oligosaccharides
Di, tri, tetra, penta, up to 9 or 10
Most important are the disaccharides
Polysaccharides or glycans
Homopolysaccharides
Heteropolysaccharides
Complex carbohydrates
 Monosaccharides
also known as simple sugars
classified by 1. the number of carbons and 2.
whether aldoses or ketoses
most (99%) are straight chain compounds
D-glyceraldehyde is the simplest of the aldoses
(aldotriose)
all other sugars have the ending ose (glucose,
galactose, ribose, lactose, etc)
 Aldose sugars
H H H H H

C O C O C O C O C O

(H C OH)n H C OH H C OH H C OH H C OH

CH2OH CH2OH H C OH H C OH H C OH

Aldose Aldotriose CH2OH H C OH H C OH

n=1
Aldotetrose CH2OH
n=2 H C OH
Aldopentose
CH2OH
n=3
Aldohexose
n=4
 Ketose sugars

CH2OH CH2OH CH2OH

CH2OH
C O C O CH2OH
C O
C O
(H C OH)n H C OH C O
H C OH
CH2OH
CH2OH H C OH H C OH
CH2OH
CH2OH H OH
Ketose Ketotriose Ketotetrose
n=1 Ketopentose H C OH
n=0
n=2
CH2OH
Ketohexose
n=3
Structure of a simple aldose and a simple ketose
 Structural representation of
sugars
Fisher projection: straight chain
representation
Haworth projection: simple ring in
perspective
Conformational representation: chair
and boat configurations
 Rules for drawing Haworth
projections
draw either a six or 5-membered ring
including oxygen as one atom
O O

most aldohexoses are six-membered

aldotetroses, aldopentoses, ketohexoses are
5-membered
 Rules for drawing Haworth
projections
next number the ring clockwise starting next to
the oxygen
5
O O
4 1 4 1

3 2 3 2

if the substituent is to the right in the Fisher

projection, it will be drawn down in the
Haworth projection (Down-Right Rule)
 Rules for drawing Haworth
projections
for D-sugars the highest numbered
carbon (furthest from the carbonyl) is
drawn up. For L-sugars, it is drawn down
for D-sugars, the OH group at the
anomeric position is drawn down for
and up for . For L-sugars is up and
is down
D-glucose can cyclize in two
ways forming either furanose or
pyranose structures
D-ribose and other five-carbon
saccharides can form either
furanose or pyranose structures
Chair and boat conformations of a pyranose sugar

2 possible chair conformations

of -D-glucose
 Optical isomerism
A property exhibited by any compound
whose mirror images are non-
superimposable
Asymmetric compounds rotate plane
polarized light
 POLARIMETRY
Measurement of optical activity in chiral or
asymmetric molecules using plane polarized light
Molecules may be chiral because of certain atoms or
because of chiral axes or chiral planes

Measurement uses an instrument called a

polarimeter (Lippich type)

Rotation is either (+) dextrorotatory or (-)

levorotatory
New polarimeters usually connected to computer and printer
 polarimetry
Magnitude of rotation depends upon:
1. the nature of the compound
2. the length of the tube (cell or sample container) usually
expressed in decimeters (dm)
3. the wavelength of the light source employed; usually either
sodium D line at 589.3 nm or mercury vapor lamp at 546.1
nm
4. temperature of sample
5. concentration of analyte in grams per 100 ml
 observed x 100
[ ] D
T
=
lxc

D = Na D line
T = temperature oC
obs : observed rotation in degree (specify solvent)
l = length of tube in decimeter
c = concentration in grams/100ml
[] = specific rotation
 Specific rotation of various
carbohydrates at 20oC
D-glucose +52.7
D-fructose -92.4
D-galactose +80.2
L-arabinose +104.5
D-mannose +14.2
D-arabinose -105.0
D-xylose +18.8
Lactose +55.4
Sucrose +66.5
Maltose+ +130.4
Invert sugar -19.8
Dextrin +195
 Enantiomers and epimers
H H
H H C O C O
C O C O HO C H HO C H
H C OH OH C H HO C H HO C H
H C OH OH C H H C OH HO C H
CH2OH CH2OH
H C OH H C OH
these two aldotetroses are enantiomers.
They are stereoisomers that are mirror CH2OH CH2OH
images of each other
these two aldohexoses are C-4 epimers.
they differ only in the position of the
hydroxyl group on one asymmetric carbon
(carbon 4)
 Reactions of monosaccharides
Carbonyl reactions:
Osazone formation
Cyanohydrin reaction
Reduction
Oxidation
Action of base
Action of acid
Ring chain tautomerism
Alcohol reactions
Glycoside formation
Ether formation
Ester formation
 Properties
Differences in structures of sugars are
responsible for variations in properties
Physical
Crystalline form; solubility; rotatory power
Chemical
Reactions (oxidations, reductions, condensations)
Physiological
Nutritive value (human, bacterial); sweetness;
absorption
 Formation of osazones
once used for the identification of sugars
consists of reacting the monosaccharide with
phenylhydrazine
a crystalline compound with a sharp melting
point will be obtained
D-fructose and D-mannose give the same
osazone as D-glucose
seldom used for identification; we now use
HPLC or mass spectrometry
 Cyanohydrin formation
reaction of an aldose with HCN
used to increase the chain length of
monosaccharides
results in a cyanohydrin which is then
hydrolyzed to an acid and reduced to the
aldehyde
known as the Fischer-Kiliani synthesis
can prepare all monosaccharides from D-
glyceraldehyde
 Oxidation reactions
Aldoses may be oxidized to 3 types of acids
Aldonic acids: aldehyde group is converted to a
carboxyl group ( glucose gluconic acid)
Uronic acids: aldehyde is left intact and primary
alcohol at the other end is oxidized to COOH
Glucose --- glucuronic acid
Galactose --- galacturonic acid
Saccharic acids (glycaric acids) oxidation at both
ends of monosaccharide)
Glucose ---- saccharic acid
Galactose --- mucic acid
Mannose --- mannaric acid
 Glucose oxidase
glucose oxidase converts glucose to gluconic
acid and hydrogen peroxide
when the reaction is performed in the presence
of peroxidase and o-dianisidine a yellow color is
formed
this forms the basis for the measurement of
urinary and blood glucose
Testape, Clinistix, Diastix (urinary glucose)
Dextrostix (venous glucose)
 Reduction
either done catalytically (hydrogen and a
catalyst) or enzymatically
the resultant product is a polyol or sugar
alcohol (alditol)
glucose form sorbitol (glucitol)
mannose forms mannitol
fructose forms a mixture of mannitol and
sorbitol
glyceraldehyde gives glycerol
Sructures of some sugar alcohols
 Sugar alcohols are very useful
intermediates
Mannitol is used as an osmotic diuretic
Glycerol is used as a humectant and can be nitrated to
nitroglycerin
Sorbitol can be dehydrated to tetrahydropyrans and
tetrahydrofuran compounds (sorbitans)
Sorbitans are converted to detergents known as spans
and tweens (used in emulsification procedures)
Sorbitol can also be dehydrated to 1,4,3,6-dianhydro-D-
sorbitol (isosorbide) which is nitrated to ISDN and
ISMN (both used in treatment of angina)
Formation of spans and tweens
OH
CH2
O
SORBITOL CH
OH THF compound

OH OH
1,4-SORBITAN
O
O
CH2 (O-C2H4) O C R
CH2 O C R O
CH (O-C2H4)nOH
O
CH
OH
HO (C2H4-O)x (O-C2H4)x OH
OH OH
TWEENS (form O/W emulsions)
SPANS (form W/O emulsions)
 Action of strong acids on
monosaccharides
monosaccharides are normally stable to dilute
acids, but are dehydrated by strong acids
D-ribose when heated with concentrated HCl
yields furfural (commercial route for the
production of THF (tetrahydrofuran)
D-glucose under the same conditions yields 5-
hydroxymethyl furfural
Basis for the Molisch test sensitive test for the
detection of carbohydrates
Molisch test for carbohydrates
 Action of base on sugars
Sugars are weak acids and can form salts at high pH
A 1,2-enediol salt is formed as the result
This allows the interconversion of D-mannose, D-
fructose and D-glucose
The reaction is known as the Lobry de Bruyn-Alberta
von Eckenstein reaction
 Action of base on sugars
enediols obtained by the action of base are quite
susceptible to oxidation when heated in the presence of
an oxidizing agent
copper sulfate is frequently used as the oxidizing agent
and a red preciptate of Cu2O is obtained
sugars which give this reaction are known as reducing
sugars
Fehlings solution : KOH or NaOH and CuSO4
Benedicts solution: Na2CO3 and CuSO4
Clinitest tablets are used to detect urinary glucose in
diabetics
 Special monosaccharides: deoxy
sugars
These are monosaccharides which lack
one or more hydroxyl groups on the
molecule
one quite ubiquitous deoxy sugar is 2-
deoxy ribose which is the sugar found in
DNA
6-deoxy-L-mannose (L-rhamnose) is used
as a fermentative reagent in bacteriology
examples of deoxysugars
Several sugar esters important
in metabolism
Special monosaccharides: amino sugars
Constituents of mucopolysaccharides
Condensation reactions: acetal and ketal formation
The anomeric forms of
methyl-D-glucoside
Examples of glycosides
 Oligosaccharides
Most common are the disaccharides
Sucrose, lactose, and maltose
Maltose hydrolyzes to 2 molecules of D-glucose
Lactose hydrolyzes to a molecule of glucose and a
molecule of galactose
Sucrose hydrolyzes to a moledule of glucose and
a molecule of fructose
 Sucrose
-D-glucopyranosido--D-fructofuranoside
-D-fructofuranosido--D-glucopyranoside
also known as tablet sugar
commercially obtained from sugar cane or
sugar beet
hydrolysis yield glucose and fructose (invert
sugar) ( sucrose: +66.5o ; glucose +52.5o;
fructose 92o)
used pharmaceutically to make syrups, troches
Sugar cane

Sugar beet
Sucralfate (Carafate)
 Lactose
-D-galactose joined to D-glucose via (1,4)
linkage
milk contains the alpha and beta-anomers in a
2:3 ratio
-lactose is sweeter and more soluble than
ordinary - lactose
used in infant formulations, medium for
penicillin production and as a diluent in
pharmaceuticals
 Maltose
2-glucose molecules joined via (1,4) linkage
known as malt sugar
produced by the partial hydrolysis of starch
(either salivary amylase or pancreatic amylase)
used as a nutrient (malt extract; Hordeum
vulgare); as a sweetener and as a fermentative
reagent
 Lactulose
galactose--(1,4)-fructose
a semi-synthetic disaccharide (not naturally
occurring)
not absorbed in the GI tract
used either as a laxative (Chronulac) or in the
management of portal systemic encephalopathy
(Cephulac)
metabolized in distal ileum and colon by bacteria
to lactic acid, formic acid and acetic acid (remove
ammonia)
 Less common glucose
disaccharides

Laminaribiose (beta 1,3)

Isomaltose (alpha 1,6)

Cellobiose (beta 1,4)

Gentiobiose (beta 1,6)
 Cellobiose

Cellobiose consists of 2 molecules of glucose linked by a beta-1,4 glycosidic bond

It is usually obtained by the partial hydrolysis of cellulose
 Trehalose
CH2OH H OH

H O HH H
OH H
OH H
HOH2C
HO O O OH
H OH H

TREHALOSE

Trehalose is a disaccharide that occurs naturally in insects, plants, fungi, and bacteria. The
major dietary source is mushrooms. Trehalose is used in bakery goods, beverages,
confectionery, fruit jam, breakfast cereals, rice, and noodles as a texturizer, stabilizer,
humectant, or formulation aid with a low sweetening intensity
 Sucralose (Splenda)

About 600 times more sweet than sucrose

 Oligosaccharides
Trisaccharide: raffinose (glucose,
galactose and fructose)
Tetrasaccharide: stachyose (2 galactoses,
glucose and fructose)
Pentasaccharide: verbascose (3
galactoses, glucose and fructose)
Hexasaccharide: ajugose (4 galactoses,
glucose and fructose)
Honey also contains glucose and fructose along with
some volatile oils
Structures of some
oligosaccharides
starch
Structures of some oligosaccharides
 Structures of some oligosaccharides

An enzymatic product (Beano) can be used to prevent

the flatulence
Oligosaccharides occur widely as components of
antibiotics derived from various sources
 Polysaccharides or glycans
homoglycans (starch, cellulose, glycogen, inulin)
heteroglycans (gums, mucopolysaccharides)
characteristics:
polymers (MW from 200,000)
White and amorphous products (glassy)
not sweet
not reducing; do not give the typical aldose or ketose
reactions)
form colloidal solutions or suspensions
 Starch
most common storage polysaccharide in
plants
composed of 10 30% amylose and
70-90% amylopectin depending on the
source
the chains are of varying length, having
molecular weights from several
thousands to half a million
 Starch
Main sources of starch are rice, corn,
wheat, potatoes and cassava
A storage polysaccharide
Starch is used as an excipient, a binder in
medications to aid the formation of
tablets.
Industrially it has many applications such
as in adhesives, paper making, biofuel,
textiles
Amylose and amylopectin are the 2 forms of starch. Amylopectin
is a highly branched structure, with branches occurring every 12
to 30 residues
suspensions of amylose
in water adopt a helical
conformation

iodine (I2) can insert in

the middle of the amylose
helix to give a blue color
that is characteristic and
diagnostic for starch
(in starch)

(in cellulose)
 Cellulose
Polymer of -D-glucose attached by (1,4) linkages
Only digested and utilized by ruminants (cows, deers,
giraffes, camels)
A structural polysaccharide
Yields glucose upon complete hydrolysis
Partial hydrolysis yields cellobiose
Most abundant of all carbohydrates
Cotton flax: 97-99% cellulose
Wood: ~ 50% cellulose
Gives no color with iodine
Held together with lignin in woody plant tissues
Lignin
 Structure of cellulose

Chains are arranged in a parallel pattern

Linear structures of cellulose and chitin
(2 most abundant polysaccharides)
 Products obtained from cellulose
Microcrystalline cellulose : used as binder-
disintegrant in tablets
Methylcellulose: suspending agent and bulk laxative
Oxidized cellulose: hemostat
Sodium carboxymethyl cellulose: laxative
Cellulose acetate: rayon; photographic film; plastics
Cellulose acetate phthalate: enteric coating
Nitrocellulose: explosives; collodion (pyroxylin)
 Glycogen
also known as animal starch
stored in muscle and liver (mostly)
present in cells as granules (high MW)
contains both (1,4) links and (1,6) branches
at every 8 to 12 glucose unit (more frequent
than in starch)
complete hydrolysis yields glucose
glycogen and iodine gives a red-violet color
hydrolyzed by both and -amylases and by
glycogen phosphorylase
 Inulin
-(1,2) linked fructofuranoses
linear only; no branching Jerusalem artichokes
lower molecular weight than starch
colors yellow with iodine
hydrolysis yields fructose
sources include onions, garlic, dandelions and
jerusalem artichokes
used as diagnostic agent for the evaluation of
glomerular filtration rate (renal function test)
 Chitin
chitin is the second most abundant carbohydrate
polymer
Like cellulose, chitin is a structural polymer
present in the cell wall of fungi and in the
exoskeletons of crustaceans, insects and spiders
chitin is used commercially in coatings (extends
the shelf life of fruits and meats)
A chitin derivative binds to iron atoms in meat
and slows the rancidity process
 Chitin
Chitin is the second most
abundant carbohydrate
polymer
Present in the cell wall of
fungi and in the
exoskeletons of crustaceans,
insects and spiders
Chitin is used commercially
in coatings (extends the
shelf life of fruits and
meats)
 Dextrans
products of the reaction of glucose and the enzyme
transglucosidase from Leuconostoc mesenteroides
contains (1,4), (1,6) and (1,3) linkages
MW: 40,000; 70,000; 75,000
used as plasma extenders (treatment of shock)
also used as molecular sieves to separate proteins
and other large molecules (gel filtration
chromatography)
components of dental plaques
 Dextrins
produced by the partial hydrolysis of
starch along with maltose and glucose
dextrins are often referred to as either
amylodextrins, erythrodextrins or
achrodextrins
used as mucilages (glues)
also used in infant formulas (prevent the
curdling of milk in babys stomach)
 Glycoproteins and
proteoglycans
Glycoproteins are proteins conjugated to
saccharides lacking a serial repeating unit
In glycoprotein the protein>>>carbohydrate
Example include enzymes, immunoglobulins or antibodies,
certain hormones
Proteoglycans are proteins conjugated to
polysaccharides with serial repeating units
Here carbohydrate>>> protein
Proteoglycans modulate cell processes and make cartilage
flexible and resilient
 Glycosaminoglycans
they are the polysaccharide chains of
proteoglycans
they are linked to the protein core via a serine
or threonine (O-linked)
the chains are linear (unbranched)
the glycosaminoglycan chains are long (over
100 monosaccharides)
they are composed of repeating disaccharides
 Glycosaminoglycans

Involved in a variety of extracellular functions; chondroitin

is found in tendons, cartilage and other connective tissues
 Glycosaminoglycans

A characteristic of glycosaminoglycans is the presence

of acidic functionalities (carboxylate and/or sulfates)
 Hyaluronic acid derivatives
several products are used in the
management of osteoarthritis symptoms
Hyalagan and Synvisc
others are used as ophthalmic surgical
adjuncts in cataract extractions,
intraocular lens implantation, corneal
transplant and retinal attachment
surgery (Healon, Amvisc, AMO Vitrax)
Glycosaminoglycans
 Pentosan polysulfate (Elmiron)

Pentosan polysulfate sodium is a semi-synthetically produced heparin-like macromolecular

carbohydrate derivative which chemically and structurally resembles glycosaminoglycans. It
is used orally to treat interstitial cystitis. Only about 3% of the administered dose is absorbed.
 Pentosan polysulfate
This medication was developed for the treatment of a human
disease called intestitial cystitis that features recurring pelvic pain
and painful urination. This condition is believed to stem from
defects in the biochemical lining of the urinary bladder

The lining of the bladder is made of a substance called

glycosaminoglycan, the same water absorbent material that makes
up the bulk of cartilage. Pentosan polysulfate sodium is a semi-
synthetic carbohydrate derivative that has a similar structure to
glycosaminoglycan. The thinking is that pentosan polysulfate
sodium is able to replenish the bladder lining (though the true
mechanism of action remains unknown).
 Pectins
pectins are heteropolysaccharides found in the pulp of fruits
(citrus, apples)
on hydrolysis pectins yield galacturonic acid, galactose, arabinose,
methanol and acetic acid
pectins are composed of galactans and arabans
used as gelling agents (to make jellies)
 Gums
widely used in the food and pharmaceutical
industry
used as: suspending agents, gelling agents,
thickening agents, emulsifiers, foam stabilizers,
crystallization inhibitors, adhesives, binding
agents and demulcents
agar, tragacanth, karaya, carrageenan, guar
gum, gum arabic (acacia), furcellaran, sodium
alginate, locust bean gum
 Gum karaya
Also known as sterculia gum
Hydrolysis yields galactose, rhamnose and
galacturonic acid
High molecular weight (9,500.000)
Originates from the exudate of a tree native to
India
Uses in pharmacy: bulk laxative and denture
adhesive
Uses in food: confer stability through binding
and emulsifying
 Agar or agar-agar
Derived from seaweeds
A mixture of agarose and agaropectin (mostly galactose subunits
MW 120,000)
Used as a laxative, vegetarian gelatin substitute, thickener for
soups, jellies, ice cream
In microbiology as a growth media
 Gum arabic
Also known as gum acacia, chaar gund or meska
Harvested from acacia trees in Sudan, Somalia and Senegal
Used pharmaceutically as a binder, emulsifying agent, suspending or
viscosity enhancer
Also used in soft drinks, gummy candies, marshmallows
Other uses: water color painting, shoe polish, pyrotechnics, adhesive
 Tragacanth
Natural gum of the dried sap of several species of
Middle eastern legumes (Astragalus species)
Iran is the largest producer of this gum
Used in pharmaceuticals and foods as an emulsifier,
thickener, stabilizer and texturant additive
Gum tragacanth
 Carrageenan
Isolated from red seaweeds
3 commercial classes: kappa, iota, and lambda
High molecular weight polysaccharide made up of repeating galalactose
units and 3, 6-anhydrogalactose both sulfated and non-sulfated
Used as thickening and stabilizing agent in both the food and
pharmaceutical industries
 Sodium alginate
Extracted from the cell walls of brown algae
Used in the food industry to increase viscosity and as an emulsifier
Used in the preparation of dental impressions
In biochemistry labs for immobilizing enzymes
In textile industry for reactive dye printing
 Bacterial cell wall
provide strength and rigidity for the
organism
consists of a polypeptide-polysaccharide
known as petidoglycan or murein
determines the Gram staining
characteristic of the bacteria
Structure of
peptidoglycan
Cell wall of Gram-positive
bacteria
Gram-negative bacteria
Cross-section of the cell
wall of a gram-negative
organism such as E.coli
Lipopolysaccharide (LPS) coats the
outer membrane of Gram-negative
bacteria.
the lipid portion of the LPS is embedded
in the outer membrane and is linked to
a complex polysaccharide
Teichoic acids are covalently linked to the peptidoglycan of gram-positive
bacteria. These polymers of glycerol phosphate (a and b) or ribitol phosphate
(c) are linked by phosphodiester bonds
Mycobacterial cell wall
 Glycosylated proteins
Usually done as a post-translational process
(enzymatic process)
Not to be confused with glycation (non-
enzymatic process)
Glycosylation is important for protein folding
and for stability
Process is site-specific
Proteins can contain either O-linked
oligosaccharides or N-linked oligosaccharides
Serine or threonine O-linked saccharides
appears to occur in the Golgi
 Aspargine N-linked glycoproteins

Involves dolichol, a polyprenoid carrier molecule in the ER lumen of the cell

These glycoproteins are found in
The blood of Arctic and Antarctic
fish enabling these to live at sub-
zero water temperatures
Some of the oligosaccharides found in N-linked glycoproteins
Some of the oligosaccharides found in N-linked glycoproteins
 A portion of the structure of heparin

Heparin is a carbohydrate with anticoagulant properties. It is used in blood

banks to prevent clotting and in the prevention of blood clots in patients
recovering from serious injury or surgery

Numerous derivatives of heparin have been made (LMWH: enoxaparin

(Lovenox), dalteparin (Fragmin), tinzaparin (Innohep), fondaparinux
Hyaluronate:
material used to
cement the cells
into a tissue
 Lectins
Proteins that bind carbohydrates with high
specificity and with moderate to high affinity
Found in all organisms (plants, animals, bacteria and
viruses
Function in cell-cell recognition, signaling, and adhesion
processes
Plant lectins: concanavalin A, wheat germ agglutinin, ricin
Animal lectins: galectin-1, selectins
Bacterial lectins: enterotoxin, cholera toxin
Viral lectins: influenza virus hemagglutinin, polyoma virus
protein-1
 Influenza virus
Is able to attach to host cells through interactions with
oligosaccharides
Lectin on virus is HA (hemagglutinin) protein
essential for entry and infection
Once it has replicated in the host cell, the new virus
must bud out to infect other cells
A viral sialidase (neuraminidase) trims the terminal
sialic acid residue from the host cells oligosaccharide
This action releases the viral particle from its interation
with the cell and prevent aggregation with other virus
particles
 Influenza virus

N-acetylneuraminic acid (a sialic acid) Neuraminidase enzyme

Oseltamivir (Tamiflu)
Zanamivir (Relenza)
 Influenza virus
Antiviral drugs: oseltamivir (Tamiflu) and zanamivir
(Relenza)
Sugar analogs
Inhibit the viral sialidase by competing with the host
cells oligosaccharides for binding
They prevent the release of viruses from the infected
cell and also cause virus particles to aggregate both of
which block another cycle of infection
These drugs must be used as soon as symptoms are
detected (12- 24 hours)
 Selectins
Selectins are adhesion proteins found on
rolling leukocytes and on the endothelial
cells of the vascular walls
3 types are known
L-selectin found on the walls of leukocytes
E- and P-selectins found on the endothelial cells
Involved in the inflammatory response
due to bacteria and viruses
 GLYCOLIPIDS
Cerebrosides
One sugar molecule
Galactocerebroside in neuronal membranes
Glucocerebrosides elsewhere in the body
Sulfatides or sulfogalactocerebrosides
A sulfuric acid ester of galactocerebroside
Globosides: ceramide oligosaccharides
Lactosylceramide
2 sugars ( eg. lactose)
Gangliosides
Have a more complex oligosaccharide attached
Biological functions: cell-cell recognition; receptors for
hormones
 glycolipids

HO R
O

NH R'

O SUGAR polar head is a sugar

beta linkage

There are different types of glycolipids: cerebrosides, gangliosides,

lactosylceramides
 GLYCOLIPIDS
Cerebrosides
One sugar molecule
Galactocerebroside in neuronal membranes
Glucocerebrosides elsewhere in the body
Sulfatides or sulfogalactocerebrosides
A sulfuric acid ester of galactocerebroside
Globosides: ceramide oligosaccharides
Lactosylceramide
2 sugars ( eg. lactose)
Gangliosides
Have a more complex oligosaccharide attached
Biological functions: cell-cell recognition; receptors for
hormones
 Gangliosides
complex glycosphingolipids that consist
of a ceramide backbone with 3 or more
sugars esterified,one of these being a
sialic acid such as N-acetylneuraminic
acid
common gangliosides: GM1, GM2, GM3,
GD1a, GD1b, GT1a, GT1b, Gq1b
 Ganglioside nomenclature
letter G refers to the name ganglioside
the subscripts M, D, T and Q indicate
mono-, di-, tri, and quatra(tetra)-sialic-
containing gangliosides
the numerical subscripts 1, 2, and 3
designate the carbohydrate sequence
attached to ceramide
 Ganglioside nomenclature
Numerical subscripts:
1. Gal-GalNAc-Gal-Glc-ceramide
2. GalNAc-Gal-Glc-ceramide
3. Gal-Glc-ceramide
 N-Acetyl-D-galactosamine D-galactose D-glucose

CH2OH CH2OH CH2OH CH2OH

OH OH H
O O O O O
OH O OH
H H

H O H
H H H H
O
H OH H NH H OH H OH
H H
C O HO C C CH2
D-Galactose
CH3 H NH
C
O H O C O
H3C C NH O COO- C R
CHOH H

CHOH
CH2OH H
H

OH H

N-acetylneuraminidate (sialic acid)

A ganglioside (GM1)