TRINITY SCHOOL OF

MEDICINE

BIOCHEMISTRY
CARBOHYDRATES

Altered by: Dr. Michael Kazachkov

Associate Professor of Biochemistry
J.A, a twenty-six year old male had been experiencing occasional discomfort
after meals
The discomfort reached a new peak last Thursday evening about an hour after
eating a cheeseburger and a large chocolate milk shake.
He spent much of that night in pain. He had abdominal cramps and diarrhea
and also felt sick to his stomach.
He went to the clinic and saw a doctor the next day.
The doctor noted that his discomfort seemed to be associated with dining out.
J.A only experienced discomfort after dining out, especially, it seemed, after
eating his favorite fast food meal, a double cheese burger and a chocolate shake.
When asked if he used very much milk or cheese when preparing meals at
home, he told the doctor that he almost never eats meals with dairy product.
The doctor suspected that he could be lactose intolerant and order a test to
verify her suspicion.
J.A was given a lactose rich fluid to drink and had his blood glucose level
measured several times over the course of two hours.
Later, the doctor informed J.A that his blood glucose level had not risen after
drinking the lactose rich fluid and that that was evidence that he is

LACTOSE INTOLERANT
 OBJECTIVES
• Enunciate the definition of carbohydrate
• List the carbohydrates functions
• Classify carbohydrates according with the number of components
• Enunciate the definition of monosaccharides
• List the most abundant monosaccharides and their function
• Enunciate the definition of anomeric carbon atom
• List the types of monosaccharides derivatives
• Enunciate the definition of glycosidic linkage
• Enunciate the definition of glycoside and mention their biological
importance
• List the most abundant disaccharides components
• Describe the structure of: starch, glycogen and cellulose
• Enunciate the definition of glycosaminoglycans
• List the general components of glycosaminoglycans
• List the functions of glycosaminoglycans
 CARBOHYDRATES
Carbohydrates are polyhydroxyaldehydes or
polyhydroxyketones and their derivatives of:
Oxidation
Reduction
Substitution
Esterification
Acetalization
Polymerization
FUNCTION OF CARBOHYDRATES
• Biological fuel
• Storage of “energy” (biological fuel)
• Building blocks of important compounds
• Precursors of other important substances
• Structural
• Molecular sieving
• Immunogen
• Storage of water
• Cellular cement
• Anticoagulant
 CLASSIFICATION OF
CARBOHYDRATES

• Monosaccharides

• Oligosaccharides

• Polysaccharides
 MONOSACCHARIDES
Monosaccharides are polyhydroxyaldehydes
or polyhydroxyketones and their derivatives of:
Oxidation
Reduction
Substitution
Esterification
Acetalization
 STERIC CONFORMATION OF
MONOSACCHARIDES

D-glyceraldehyde L-glyceraldehyde
D-erythrose D-threose Dihydroxyacetone D-erythrulose
CLASSIFICATION OF
MONOSACCHARIDES
ACCORDING WITH THE MAIN
CHEMICAL FUNCTION

Aldoses Ketoses
 CLASSIFICATION OF
MONOSACCHARIDES
ACCORDING WITH THE
NUMBER OF CARBON ATOMS

Trioses Aldotrioses Ketotrioses

Tetroses Aldotetroses Ketotetroses

Pentoses Aldopentoses Ketopentoses

Hexoses Aldohexoses Ketoexoses

Heptoses Aldoheptoses Ketoheptoses

Octoses Aldooctoses Ketooctoses

 SOME IMPORTANT
MONOSACCHARIDES

D-Glyceraldehyde Dihydroxyacetone D-Ribose D-Deoxyribose

D-Glucose D-Mannose D-Galactose D-Fructose

CYCLIC STRUCTURE OF
MONOSACCHARIDES

Furan

Pyrane
 ANOMERS OF
MONOSACCHARIDES

a, Anomer b, Anomer
 ANOMERS OF
MONOSACCHARIDES
• All aldopentoses and ketohexoses have
furanosic structures

• All aldohexoses and ketoheptoses have

pyranosic structure

• All monosaccharides with less than five

carbon atoms don’t have cyclic structure
 SOME IMPORTANT
MONOSACCHARIDES

a, D-Glucose b, D-Ribose a, D-Deoxyribose

a, D-Glucose
D-Mannose b, D-Galactose
D-Mannose D-Galactose
b, D-Fructose D-Fructose
 GLYCOSIDES AND
OLIGOSACCHARIDES
GLYCOSIDIC LINKAGE
GLYCOSIDIC LINKAGE AND
GLYCOSIDES
• a-O-Glycoside
a-O-Glycosidic

• b-O-Glycoside
b-O-Glycosidic

• a-N-Glycoside
a-N-Glycosidic

• b-N-Glycoside
b-N-Glycosidic
SOME IMPORTANT GLYCOSIDES
• Nucleosides
Building block of nucleic acids
Vitamins
• Cardiac glycosides
Digitalis
Ouabain
• Antibiotics
Puromycin
Aminoglycosides (kanamycin, gentamycin)
Streptomycin
MONOSACCHARIDE DERIVATIVES
• Sugar acids
Uronic acids
Aldonic acids
• Reduction derivatives
Polyalcohols
Deoxy sugars
• Amino sugars
Glycosamines
Glycosylamines
• Esterification derivatives
Phosphoric esters
Sulfuric esters
 DISACCHARIDES
They are chemical compounds resulting from the join of two
monosaccharides through a glycosidic linkage

Maltose Cellobiose

Sucrose

Lactose

Isomaltose
 POLYSACCHARIDES
They are macromolecules resulting from the
join of more than ten monosaccharides
through glycosidic linkages

CLASSIFICATION
• Homopolysaccharides
A single monosaccharide component
• Heteropolysaccharide
At least two different monosaccharides
components
 SOME IMPORTANT
HOMOPOLYSACCHARIDES

• Starch

• Glycogen

• Cellulose
 STARCH
Second most abundant carbohydrate in
nature
BIOLOGICAL FUNCTIONS
• Storage of energy in plants
• First supply of glucose in human diet
CHEMICAL COMPOSITION
• It is not a molecule but a grain with two
components
Amylose
Amylopectin
 AMYLOSE
One of the starch molecules
CHEMICAL COMPOSITION
Glucose
MONOMERIC UNIT
Maltose
CONFORMATION
Helicoidal
 AMYLOPECTIN
Second starch’s molecule
A branched molecule
CHEMICAL COMPOSITION
Glucose
MONOMERIC UNIT
Maltose and isomaltose
 GLYCOGEN
Similar to amylopectin but
more branched. One branch
every 8 to 12 glucose unit

Glycogenin
 CELLULOSE
Most abundant carbohydrate
CHEMICAL COMPOSITION
Glucose
MONOMERIC UNIT
Cellobiose
CONFORMATION
Long fibers which are held
together through hydrogen
bonds
FUNCTION
Laxative
GLYCOSAMINOGLYCANS
• Heteropolysaccharides are N-AcetylHyaluronate
Glucosamine
Glucose
Glucuronate
anionic polysaccharide
chains made of repeating
disaccharide units
• Usually they content an
amino sugar and an acid
sugar Chondrosine
Chondroitine 4-sulfate
4-sulfate
6-sulfate
N-Acetyl Glucose
Glucuronate
Galactosamine
Galactose

• Some of then have sulfate

groups
• They are abundant on the
cell surface and in the
extracellular matrix
 GLYCOSAMINOGLYCANS

KERATAN SULFATE DERMATAN SULFATE

HEPARIN
 SOME FUNCTIONS OF
GLYCOSAMINOGLYCANS
• Structural
• Regulation of water metabolism
• Cellular cement
• Biological sieve
• Biological lubricant
• Docking sites for growth factors
 ORGANIZATION OF
GLYCOSAMINOGLYCANS
Proteoglycans
They are proteins containing one or more
covalently linked glycosaminoglycan chains
Typical structure of cartilage
Cartilage can cushion
compressive forces because
these highly Hydrated
Hyaluronate
polyanions spring back after
being deformed
Keratan sulfate
Link protein
Chondroitin sulfate
Core protein
PROTEOGLYCAN AS CELLULAR
CEMENT
Actin filaments
Integrin

Proteoglycan

Fibronectin

Cross linked
fiber of collagen

Plasma membrane