Dental Biochemistry 1- (5)
Chemistry and digestion of
carbohydrates
1
DEFINITION
Carbohydrates are organic substances
composed of carbon, hydrogen and
oxygen.
2
Function of carbohydrates:
• Carbohydrates are the main sources of
energy in the body. Brain cells and RBCs are
almost wholly dependent on carbohydrates as
the energy source. Energy production from
carbohydrates will be 4 Kcal/g.
• Storage form of energy (starch and glycogen).
• Excess carbohydrate is converted to fat.
• Glycoproteins and glycolipids are components
of cell membranes and receptors,
3
• Structural unit of many organisms: Cellulose of
plants; exoskeleton of insects, cell wall of
microorganisms, mucopolysaccharides as ground
substance in higher organisms.
• Important part of nucleic acids and free
nucleotides and coenzyme.
• Major antigens are carbohydrates in nature, e.g.,
blood group substance.
• Has a biological role as a part of hormones and
their receptors and enzymes.
4
Nomenclature
• Molecules having only one actual or potential sugar
group [(CH2O)n] are called monosaccharides (e.g.
C6H12O6); they cannot be further hydrolyzed into
smaller units.
• When two monosaccharides are combined
together with elimination of a water molecule, it is
called a disaccharide (e.g. C12H22O11).
• Trisaccharides contain three sugar groups. Further
addition of sugar groups will correspondingly
produce tetrasaccharides, pentasaccharides and so
on, commonly known as oligosaccharides.5
• When more than 10 sugar units are combined, they
are generally named as polysaccharides.
• Polysaccharides having only one type of
monosaccharide units are called
homopolysaccharides and those having different
monosaccharide units are called
heteropolysaccharides.
6
Monosaccharides
They have the common formula
(CH2O)n, where n = 3 or some
larger number
7
CLASSIFICATION OF MONOSACCHARIDES
Can be carried out by one of two methods:
1) According to the number of carbon atoms
:
Trioses, Tetroses, Pentoses,
Hexoses, Heptoses, Octoses.
8
• 2) According to the characteristic
carbonyl group:
Aldehyde group or ketone group
a) Aldo sugars: Aldoses :
Monosaccharides containing aldehyde group e.g.
glucose, ribose, erythrose and glyceraldehyde.
b) Keto sugars: Ketoses :
Monosaccharides containing ketone group e.g.
fructose, ribulose and dihydroxyacetone.
9
10
STEREOISOMERS
• Compounds having same structural formula, but
differ in spatial configuration are known as
stereoisomers.
• All monosaccharides can be considered as
molecules derived from glyceraldehyde.
• Depending on the configuration of Hand OH
around the reference carbon atom, the two
mirror forms are designated as Land D forms.
• All naturally occurring sugars are D sugars.
11
12
of AldosesEpimerism
• When sugars are different from one another,
only in configuration with regard to a single
carbon atom (other than the reference carbon
atom), they are called epimers.
• For example, glucose and mannose
13
Anomerism of Sugars
• This is explained by the fact that D-glucose has
two anomers, alpha and beta varieties.
14
Monosaccharides of
physiologic importance
1-Pentoses:
• They are sugars containing 5 carbon
atoms. Ribose is a constituent of RNA
while deoxyribose is seen in DNA.
• Ribose is also seen in co-enzymes
such as ATP and NAD.
15
16
Hexoses
Galactose, Mannose andGlucose
• They are the common aldohexoses.
• Glucose is the sugar in human blood. It is the
major source of energy.
• Mannose is a constituent of many
glycoproteins. Mannose was isolated from
plant mannans; hence the name.
17
b) D-Fructose :
( Fruit sugar = Levulose). It is found in fruits, honey
and obtained from sucrose and inulin by hydrolysis.
c)D-Galactose :
It is obtained from hydrolysis of lactose (milk sugar). .
It is a constituent of galactolipids, glycoprotein.
18
19
DlSACCHARIDES
• When two monosaccharides are
combined together by glycosidic
linkage, a disaccharide is formed.
The important disaccharides are
sucrose, maltose, isomaltose and
lactose.
20
. Sucrose1
• It is the sweetening agent known as cane sugar. It is
present in sugarcane and various fruits. Hydrolysis
of sucrose will produce one molecule of glucose
and one molecule of fructose.
• ii. The enzyme producing hydrolysis of sucrose is
called sucrase.
• Sucrose is not
a reducing sugar.
21
. Lactose2
• Reducing disaccharide.
• Capable of forming osazone.
• It is only found in milk.
• By acid or lactase enzyme in the intestine,
it yields D-galactose and D-glucose
22
. Maltose3
• Maltose contains two glucose residues with
alpha1,4 linkage.
• It is found in germinating cereals and malt.
• Intermediate product of the action of amylases on
starch. It is reducing disaccharide
• Hydrolysis: By acid or by maltase enzyme into
two D-glucose units.
23
Isomaltose.4
• It is also a reducing sugar. It contains 2 glucose
units combined in alpha -1, 6 linkage.
• Partial hydrolysis of glycogen and starch
produces isomaltose.
24
POLYSACCHARIDES
• These are polymerized products of many
monosaccharide units.
• They may be homoglycans composed of
single kind of monosaccharides, e.g. starch.
glycogen and cellulose.
• Heteroglycans are composed of two or more
different monosaccharides.
25
Starch.1
• It is the reserve carbohydrate of plant as in
potatoes, rice, wheat. 10-20% is soluble part called
amylose. The insoluble part is called amylopectin.
• Amylose is made up of glucose units with alpha-
1,4 glycosidic linkages to form an unbranched long
chain.
• Amylopectin is also made up of glucose units, but
is highly branched with molecular weigh more
than 1 million. The branching points are made by
alpha-1,6 linkage (similar to isomaltose) .
26
2. Glycogen
• It is the reserve carbohydrate in animals. It is
stored in liver and muscle. About 5% of weight of
liver is made up by glycogen.
• Glycogen is composed of glucose units joined by
alpha-1 ,4 and alpha-1 ,6 glycosidic linkages.
3. Cellulose
• It is the chief carbohydrate in plants.
• The enzyme act on hydrolysis of cellulose is absent
in animal and human digestive system, and hence
cellulose cannot be digested.
27
4. Inulin
• It is the reserve carbohydrate present in onion,
garlic, etc.
• 5. Chitin
• It is present in exoskeletons of crustacea and
insects
28
B- Heteroglycan:
These are polysaccharides containing more than one
type of sugar residues.
1.Agar:
• It is prepared from sea weeds and contains
galactose, glucose and other sugars.
• It is used as a supporting medium for
electrophoresis.
• 2. Mucopolysaccharides:
• Mucopolysaccharides or glycosaminoglycans (GAG)
are carbohydrates containing uronic acid and amino
sugars.29
3. Hyaluronic acid:
• It is present in connective tissues, tendons,
4. Heparin:
• It is an anticoagulant
• 5. Keratan sulphate:
• It is found in cornea and tendons.
30
Glycoproteins and Mucoproteins
• When the carbohydrate chains are attached to a
polypeptide chain it is called a proteoglycan.
• If the carbohydrate content is less than 10%, it is
generally named as a glycoprotein.
• If the carbohydrate content is more than 10% it is a
mucoprotein.
• They are seen in almost all tissues and cell
membranes.
31
Digestion of carbohydrates
• Cooking helps in breaking of glycosidic
linkages in polysaccharides and thus makes
the digestion process easier.
• In the diet carbohydrates are available as
polysaccharides (starch, glycogen), and to a
minor extent, as disaccharides (sucrose and
lactose).
32
• This process of digestion starts in mouth by
the salivary alpha-amylase. However, the
time available for digestion in the mouth is
limited. The gastric hydrochloric acid will
inhibit the action of salivary amylase.
• In the pancreatic juice another alpha-amylase
is available which will hydrolyze the alpha-1,4
glycosidic linkages randomly, so as to produce
smaller subunits like maltose, isomaltose,
dextrin and oligosaccharides.
33
• The intestinal juice (succus entericus)
and brush border of intestinal cells
contain enzymes, which will hydrolyze
disaccharides into component
monosaccharaides.
• These enzymes are sucrase, maltase,
isomaltase and lactase.
• The monosaccharides are then
absorbed.
34
Lactose intolerance
• This is produced by the deficiency of lactase.
This enzyme hydrolyses lactose to glucose and
galactose.
• In this condition, lactose accumulate in the
gut produce irritant diarrhea.
• If milk is withdrawn temporarily, the diarrhea
will be limited. Curd is also an effective
treatment, because the lactobacilli present in
curd contains the enzyme lactase.
• Lactase activity is high during infancy and it
decreases to adult levels by 5-7 years of age.35
Absorption of carbohydrates
• Only monosaccharides are absorbed by the
intestine. Minute quantities of disaccharides that
may be absorbed, are immediately eliminated
through kidneys.
• The duodenum and upper jejunum absorb the
bulk of the dietary sugars.
• Insulin is not required for the uptake of glucose by
intestinal cells.
36
• However, different sugars have different
mechanisms of absorption.
1. galactose and glucose are transported into the
mucosal cells by an active, energy-requiring
process that involves a specific transport protein
and requires a concurrent uptake of sodium ions
(sodium-dependent monosaccharide
transporter SGluT).
2. Fructose uptake requires a sodium-independent
monosaccharide transporter (GLUT-5) for its
absorption.
3. All three monosaccharides are transported from
the intestinal mucosal cell into the portal circulation
by yet another transporter, GLUT-2.
37
38

Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01

  • 1.
    Dental Biochemistry 1-(5) Chemistry and digestion of carbohydrates 1
  • 2.
    DEFINITION Carbohydrates are organicsubstances composed of carbon, hydrogen and oxygen. 2
  • 3.
    Function of carbohydrates: •Carbohydrates are the main sources of energy in the body. Brain cells and RBCs are almost wholly dependent on carbohydrates as the energy source. Energy production from carbohydrates will be 4 Kcal/g. • Storage form of energy (starch and glycogen). • Excess carbohydrate is converted to fat. • Glycoproteins and glycolipids are components of cell membranes and receptors, 3
  • 4.
    • Structural unitof many organisms: Cellulose of plants; exoskeleton of insects, cell wall of microorganisms, mucopolysaccharides as ground substance in higher organisms. • Important part of nucleic acids and free nucleotides and coenzyme. • Major antigens are carbohydrates in nature, e.g., blood group substance. • Has a biological role as a part of hormones and their receptors and enzymes. 4
  • 5.
    Nomenclature • Molecules havingonly one actual or potential sugar group [(CH2O)n] are called monosaccharides (e.g. C6H12O6); they cannot be further hydrolyzed into smaller units. • When two monosaccharides are combined together with elimination of a water molecule, it is called a disaccharide (e.g. C12H22O11). • Trisaccharides contain three sugar groups. Further addition of sugar groups will correspondingly produce tetrasaccharides, pentasaccharides and so on, commonly known as oligosaccharides.5
  • 6.
    • When morethan 10 sugar units are combined, they are generally named as polysaccharides. • Polysaccharides having only one type of monosaccharide units are called homopolysaccharides and those having different monosaccharide units are called heteropolysaccharides. 6
  • 7.
    Monosaccharides They have thecommon formula (CH2O)n, where n = 3 or some larger number 7
  • 8.
    CLASSIFICATION OF MONOSACCHARIDES Canbe carried out by one of two methods: 1) According to the number of carbon atoms : Trioses, Tetroses, Pentoses, Hexoses, Heptoses, Octoses. 8
  • 9.
    • 2) Accordingto the characteristic carbonyl group: Aldehyde group or ketone group a) Aldo sugars: Aldoses : Monosaccharides containing aldehyde group e.g. glucose, ribose, erythrose and glyceraldehyde. b) Keto sugars: Ketoses : Monosaccharides containing ketone group e.g. fructose, ribulose and dihydroxyacetone. 9
  • 10.
  • 11.
    STEREOISOMERS • Compounds havingsame structural formula, but differ in spatial configuration are known as stereoisomers. • All monosaccharides can be considered as molecules derived from glyceraldehyde. • Depending on the configuration of Hand OH around the reference carbon atom, the two mirror forms are designated as Land D forms. • All naturally occurring sugars are D sugars. 11
  • 12.
  • 13.
    of AldosesEpimerism • Whensugars are different from one another, only in configuration with regard to a single carbon atom (other than the reference carbon atom), they are called epimers. • For example, glucose and mannose 13
  • 14.
    Anomerism of Sugars •This is explained by the fact that D-glucose has two anomers, alpha and beta varieties. 14
  • 15.
    Monosaccharides of physiologic importance 1-Pentoses: •They are sugars containing 5 carbon atoms. Ribose is a constituent of RNA while deoxyribose is seen in DNA. • Ribose is also seen in co-enzymes such as ATP and NAD. 15
  • 16.
  • 17.
    Hexoses Galactose, Mannose andGlucose •They are the common aldohexoses. • Glucose is the sugar in human blood. It is the major source of energy. • Mannose is a constituent of many glycoproteins. Mannose was isolated from plant mannans; hence the name. 17
  • 18.
    b) D-Fructose : (Fruit sugar = Levulose). It is found in fruits, honey and obtained from sucrose and inulin by hydrolysis. c)D-Galactose : It is obtained from hydrolysis of lactose (milk sugar). . It is a constituent of galactolipids, glycoprotein. 18
  • 19.
  • 20.
    DlSACCHARIDES • When twomonosaccharides are combined together by glycosidic linkage, a disaccharide is formed. The important disaccharides are sucrose, maltose, isomaltose and lactose. 20
  • 21.
    . Sucrose1 • Itis the sweetening agent known as cane sugar. It is present in sugarcane and various fruits. Hydrolysis of sucrose will produce one molecule of glucose and one molecule of fructose. • ii. The enzyme producing hydrolysis of sucrose is called sucrase. • Sucrose is not a reducing sugar. 21
  • 22.
    . Lactose2 • Reducingdisaccharide. • Capable of forming osazone. • It is only found in milk. • By acid or lactase enzyme in the intestine, it yields D-galactose and D-glucose 22
  • 23.
    . Maltose3 • Maltosecontains two glucose residues with alpha1,4 linkage. • It is found in germinating cereals and malt. • Intermediate product of the action of amylases on starch. It is reducing disaccharide • Hydrolysis: By acid or by maltase enzyme into two D-glucose units. 23
  • 24.
    Isomaltose.4 • It isalso a reducing sugar. It contains 2 glucose units combined in alpha -1, 6 linkage. • Partial hydrolysis of glycogen and starch produces isomaltose. 24
  • 25.
    POLYSACCHARIDES • These arepolymerized products of many monosaccharide units. • They may be homoglycans composed of single kind of monosaccharides, e.g. starch. glycogen and cellulose. • Heteroglycans are composed of two or more different monosaccharides. 25
  • 26.
    Starch.1 • It isthe reserve carbohydrate of plant as in potatoes, rice, wheat. 10-20% is soluble part called amylose. The insoluble part is called amylopectin. • Amylose is made up of glucose units with alpha- 1,4 glycosidic linkages to form an unbranched long chain. • Amylopectin is also made up of glucose units, but is highly branched with molecular weigh more than 1 million. The branching points are made by alpha-1,6 linkage (similar to isomaltose) . 26
  • 27.
    2. Glycogen • Itis the reserve carbohydrate in animals. It is stored in liver and muscle. About 5% of weight of liver is made up by glycogen. • Glycogen is composed of glucose units joined by alpha-1 ,4 and alpha-1 ,6 glycosidic linkages. 3. Cellulose • It is the chief carbohydrate in plants. • The enzyme act on hydrolysis of cellulose is absent in animal and human digestive system, and hence cellulose cannot be digested. 27
  • 28.
    4. Inulin • Itis the reserve carbohydrate present in onion, garlic, etc. • 5. Chitin • It is present in exoskeletons of crustacea and insects 28
  • 29.
    B- Heteroglycan: These arepolysaccharides containing more than one type of sugar residues. 1.Agar: • It is prepared from sea weeds and contains galactose, glucose and other sugars. • It is used as a supporting medium for electrophoresis. • 2. Mucopolysaccharides: • Mucopolysaccharides or glycosaminoglycans (GAG) are carbohydrates containing uronic acid and amino sugars.29
  • 30.
    3. Hyaluronic acid: •It is present in connective tissues, tendons, 4. Heparin: • It is an anticoagulant • 5. Keratan sulphate: • It is found in cornea and tendons. 30
  • 31.
    Glycoproteins and Mucoproteins •When the carbohydrate chains are attached to a polypeptide chain it is called a proteoglycan. • If the carbohydrate content is less than 10%, it is generally named as a glycoprotein. • If the carbohydrate content is more than 10% it is a mucoprotein. • They are seen in almost all tissues and cell membranes. 31
  • 32.
    Digestion of carbohydrates •Cooking helps in breaking of glycosidic linkages in polysaccharides and thus makes the digestion process easier. • In the diet carbohydrates are available as polysaccharides (starch, glycogen), and to a minor extent, as disaccharides (sucrose and lactose). 32
  • 33.
    • This processof digestion starts in mouth by the salivary alpha-amylase. However, the time available for digestion in the mouth is limited. The gastric hydrochloric acid will inhibit the action of salivary amylase. • In the pancreatic juice another alpha-amylase is available which will hydrolyze the alpha-1,4 glycosidic linkages randomly, so as to produce smaller subunits like maltose, isomaltose, dextrin and oligosaccharides. 33
  • 34.
    • The intestinaljuice (succus entericus) and brush border of intestinal cells contain enzymes, which will hydrolyze disaccharides into component monosaccharaides. • These enzymes are sucrase, maltase, isomaltase and lactase. • The monosaccharides are then absorbed. 34
  • 35.
    Lactose intolerance • Thisis produced by the deficiency of lactase. This enzyme hydrolyses lactose to glucose and galactose. • In this condition, lactose accumulate in the gut produce irritant diarrhea. • If milk is withdrawn temporarily, the diarrhea will be limited. Curd is also an effective treatment, because the lactobacilli present in curd contains the enzyme lactase. • Lactase activity is high during infancy and it decreases to adult levels by 5-7 years of age.35
  • 36.
    Absorption of carbohydrates •Only monosaccharides are absorbed by the intestine. Minute quantities of disaccharides that may be absorbed, are immediately eliminated through kidneys. • The duodenum and upper jejunum absorb the bulk of the dietary sugars. • Insulin is not required for the uptake of glucose by intestinal cells. 36
  • 37.
    • However, differentsugars have different mechanisms of absorption. 1. galactose and glucose are transported into the mucosal cells by an active, energy-requiring process that involves a specific transport protein and requires a concurrent uptake of sodium ions (sodium-dependent monosaccharide transporter SGluT). 2. Fructose uptake requires a sodium-independent monosaccharide transporter (GLUT-5) for its absorption. 3. All three monosaccharides are transported from the intestinal mucosal cell into the portal circulation by yet another transporter, GLUT-2. 37
  • 38.