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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
Epimerism of Aldoses
• 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
       Glucose, Mannose and Galactose

• 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
1. Sucrose
• 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
2. Lactose
•   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
3. Maltose
• 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
4. Isomaltose
• 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
1. Starch
• 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

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Lec 5 level 3-de(chemistry of carbohydrates)

  • 1. Dental Biochemistry 1- (5) Chemistry and digestion of carbohydrates 1
  • 2. DEFINITION Carbohydrates are organic substances 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 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
  • 5. 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
  • 6. • 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
  • 7. Monosaccharides They have the common formula (CH2O)n, where n = 3 or some larger number 7
  • 8. 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
  • 9. • 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. 10
  • 11. 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. 12
  • 13. Epimerism of Aldoses • 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
  • 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. 16
  • 17. Hexoses Glucose, Mannose and Galactose • 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. 19
  • 20. DlSACCHARIDES • When two monosaccharides are combined together by glycosidic linkage, a disaccharide is formed. The important disaccharides are sucrose, maltose, isomaltose and lactose. 20
  • 21. 1. Sucrose • 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
  • 22. 2. Lactose • 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
  • 23. 3. Maltose • 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
  • 24. 4. Isomaltose • 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
  • 25. 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
  • 26. 1. Starch • 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
  • 27. 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
  • 28. 4. Inulin • It is the reserve carbohydrate present in onion, garlic, etc. • 5. Chitin • It is present in exoskeletons of crustacea and insects 28
  • 29. 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
  • 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 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
  • 34. • 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
  • 35. 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
  • 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, 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. 38