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CHEMISTRY OF CARBOHYDRATES
Prepared by: Assistant professor (Biochemistry) Dr. Sumreena Mansoor
Vignette 4
Introduction: 18 year old exchange student from Nigeria.
Presenting complaint: Bloating, abdominal cramps and intermittent diarrhea ever
since arriving in Pakistan 3 months earlier.
These symptoms appear about an hour after consuming breakfast & disappear when
dairy products are removed from her diet.
Laboratory investigation: Hydrogen breath test positive
Diagnosis: Secondary lactose intolerance
Advice: She was advised to avoid dairy products and to take a tablet containing
lactase in case she did eat any product containing milk.
OBJECTIVES
 Introduction and Definition
 Isomerism in Sugars
 Classification
 Important Carbohydrates
 Biomedical Importance of Carbohydrates
INTRODUCTION
 Hydrates of carbon
 Saccharides — sugars
 Some contain N and S
 Synthesized in
• Plants
• Animals
DEFINITION
 Carbohydrates are polyhydroxylated
compounds having at least 3 carbon atoms
and a potentially active carbonyl group which
may be an aldose or a ketose group.
 Examples are: glucose, ribose.
GLYCERALDEHYDE
O
C H
HO C H
CH2OH
L-GLYCEROSE
O
C H
H C OH
CH2OH
D-GLYCEROSE
GLUCOSE
H C O
H C OH
HO C H
H C OH
H C OH
CH2OH
GLUCOSE
 ANOMERIC CARBON ATOM
The carbon atom which is part of the
carbonyl group
Alpha(α) and Beta(β) anomers differ from
each other only in respect to configuration
around anomeric carbon atom.
Alpha and Beta anomers of glucose
H OH
C
H C OH
HO C H O
H C OH
H C
H C OH
H
α-D-GLUCOPYRANOSE
HO H
C
H C OH
HO C H O
H C OH
H C
H C OH
H
β-D-GLUCOPYRANOSE
ISOMERISM IN SUGARS
 Isomers/Stereo-isomers: Compounds having
the same chemical formulae but differing in
the arrangement of their atoms in space and
having different physical properties are called
isomers.
EPIMERS
 Monosaccharides which differ in
configuration around one specific C-
atom are called epimers of one another
 C-2 epimers
• glucose and mannose
 C-4 epimers
• glucose and galactose
H C O
H C OH
HO C H
H C OH
H C OH
CH2OH
D-GLUCOSE
H C O
HO C H
HO C H
H C OH
H C OH
CH2OH
D-MANNOSE
CARBON-2 EPIMERS
CARBON-4 EPIMERS
H C O
H C OH
HO C H
H C OH
H C OH
CH2OH
D-GLUCOSE
H C O
H C OH
HO C H
HO C H
H C OH
CH2OH
D-GALACTOSE
Carbohydrates
Monosaccharides Oligosaccharides Derived
Disaccharides Carbohydrates
Aldoses Ketoses
Oxidation
Polysaccharides Reduction
Amino sugars
Homopolysaccharides Deoxy sugars
Heteropolysaccharides
CLASSIFICATION OF
CARBOHYDRATES
MONOSACCHARIDES
No of C-atoms Potentially active
carbonyl group
Trioses
Tetroses
Pentoses Aldoses Ketoses
Hexoses
Heptoses “These carbohydrates cannot
Octoses be hydrolyzed into simpler compounds”
Aldehyde CHO Ketone C O
Reducing and Non-Reducing Sugars
 Reduction is the chemist’s term for electron
gain
 A molecule that gains an electron is thus……
– “reduced”
 A molecule that donates electrons is called
a……
– “reducing agent”
 A sugar that donates electrons is called a……
– “reducing sugar”
 The electron is donated by the carbonyl
group
 Benedict’s reagent changes colour when
exposed to a reducing agent
Benedict’s Test
 Benedict’s reagent
undergoes a complex colour
change when it is reduced
 The intensity of the colour
change is proportional to the
concentration of reducing
sugar present
 The colour change sequence
is:
– Blue…
– green…
– yellow…
– orange…
– brick red
The carbonyl group -
monosaccharides
 The carbonyl group is
“free” in the straight
chain form
 But not free in the ring
form
 BUT remember – the
ring form and the
straight chain form are
interchangeable
 So all monosaccharides
are reducing sugars
 All monosaccharides
reduce Benedict’s
reagent
The carbonyl group –
disaccharides - sucrose
 In some disaccharides
e.g. sucrose both of the
carbonyl groups are
involved in the
glycosidic bond
 So there are no free
carbonyl groups
 Such sugars are called
non-reducing sugars
 They do NOT reduce
Benedict’s reagent
The carbonyl group –
disaccharides - sucrose
 The subunits of sucrose
(glucose and fructose)
are reducing sugars
 If sucrose is hydrolysed
the subunit can then act
as reducing sugars
 This is done in the lab
by acid hydrolysis
 After acid hydrolysis
sucrose will reduce
Benedict’s reagent
OLIGOSACCHARIDES
 These are the condensation products of 2 to
10 monosaccharide units
 Disaccharides: These are the condensation
products of two monosaccharide units e.g.
sucrose, lactose.
POLYSACCHARIDES
 These are the condensation products of
more than 10 molecules of monosaccharide
units
 They include starch, glycogen.
 Stores of fuel
 Structural elements of cells
POLYSACCHARIDES
Homopolysaccharides
Heteropolysaccharides
*Starch
*Glycogen Glycoseaminoglycans
*Cellulose Mucilages
*Dextrins *Hyaluronic acid
*Heparin *Agar
*Chondoitin SO4 *Vegetable
*Serum mucoids gums
*Blood gp *Pectins
polysaccharides *Hemicellulose
DERIVED CARBOHYRATES
Oxidation Reduction Amino Deoxy
Products Products Sugars Sugars
Gluconic acid Glycerol Glucosamine
Glucuronic acid Ribitol Galactoseamine
Glucaric acid Mannoseamine
Deoxyribose
“These are derived from carbohydrates by various
chemical reactions”
OH
H
OH
OH
H
CH2OH
H
H
OH
H
H
OH
H
CH2OH
H
H
DEOXYRIBOSE SUGARS
IMPORTANT CARBOHYDRATES
 MONOSACCHARIDES
 PENTOSES
 Ribose:
 Found in nucleic acids
 Forms structural elements of nucleic acid
and coenzymes
 Intermediates of pentose phosphate pathway
 ATP, NAD, NADP, flavoproteins etc
 HEXOSES
Glucose
 Found in fruits, fruit juices, hydrolysis
of starch, maltose and lactose.
 Body sugar and the principal one used
by the tissues
 Excess in the blood is called
hyperglycemia and presence in urine
(glucosuria) indicates diabetes mellitus
 Cataract due to sorbitol
Fructose
 Latin word for fruit — "fructus"
 Found in fruit juices, honey
 Released by the hydrolysis of inulin
 Main nutritional source of energy for the
spermatozoa and is found in the seminal fluid
 Can be converted to glucose in the liver
 It is the sweetest sugar
 Lack of enzymes of metabolism can lead to
essential fructosuria
Galactose
 Greek word for milk--"galact", found as a
component of lactose in milk
 Formed by the hydrolysis of lactose
 Synthesized in the lactating mammary gland
 Constituent of glycolipids and glycoproteins
 Can be converted to glucose in the liver
 Accumulation can lead to galactosemia and
cataract (galactitol)
OLIGOSACCHARIDES
Sucrose
 Known as table sugar
 α-D-glucose ------ β-D- fructose
 α-1 β-2
Sucrose
α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside
Lactose
 Synthesized by lactating mammary gland
 Milk sugar (lac-milk)
 β-D-galactose β-D-glucose
 β 1 4 linkage
 Enzyme – lactase and lactose intolerance
 Least sweet sugar – 16% of sucrose
 Possesses one potential aldehyde group
• reducing sugar
• forms osazone crystals
HOMOPOLYSACCHARIDES
Starch
 Main storage form of glucose in plants
 Polysaccharide units
• Amylose (20—28%)
• Amylopectin 72—80%)
 Polymer of α-D-glucose
 α-1 4 glycosidic linkage
 At branching points α-1 6 linkage
 No free aldehyde group
 Found in wheat, rice, corn, potatoes
Starch
Form Linear Branch
Linkage -1,4 (some
-1,6)
-1,4; -
1,6
Polymer units 200-2,000 Up to
2,000,000
Molecular
weight
Generally
<0.5 million
50-500
million
Gel formation Firm Non-
gelling to
soft
Characteristics of Amylose and Amylopectin
Characteristic Amylose Amylopectin
Glycogen
 Known as animal starch
 Present in the liver and muscle
 Both α-1 4 and α-1 6 linkages
are found
 More branched structure than starch
 Gives red color with iodine
Glycogen
A glycoside is an organic compound,
usually of plant origin, that is composed
of a sugar portion linked to a non-sugar
moiety. The sugar portion is called
glycone, while the non-sugar portion is
c a l l e d a g l y c o n e .
GLYCOSIDES
The linkage between the sugar and the
aglycone is an acetal linkage.
Types of Glycosides :
According to atoms involved in the
glycosidic linkage:
1- O-glycosides
2- C-glycosides
3- S-glycosides
4- N-glycosides
GLYCOSIDES
GLYCOSIDES
 Cardiac glycosides Digitalis useful in
Congestive cardiac failure. They contain
Steroid as aglycone.
BIOMEDICAL IMPORTANCE
OF CARBOHYDRATES
BIOMEDICAL IMPORTANCE
 Glucose — most important carbohydrate
 Glucose can be converted into
• glycogen
• ribose
• galactose
 Glycoproteins — molecular targeting
 Antibodies and blood clotting factors
 Structural components of cell membranes
 Neuronal adhesion in development of
nervous system (protein-glycan-heparan-
sulfate)
 Constituents of extra cellular matrix
 Diseases associated with carbohydrates
• Diabetes mellitus
• Galactosemia
• Lactose intolerance
• Glycogen storage diseases
7-chemistry-of-carbohydrates.ppt

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7-chemistry-of-carbohydrates.ppt

  • 1. CHEMISTRY OF CARBOHYDRATES Prepared by: Assistant professor (Biochemistry) Dr. Sumreena Mansoor
  • 2. Vignette 4 Introduction: 18 year old exchange student from Nigeria. Presenting complaint: Bloating, abdominal cramps and intermittent diarrhea ever since arriving in Pakistan 3 months earlier. These symptoms appear about an hour after consuming breakfast & disappear when dairy products are removed from her diet. Laboratory investigation: Hydrogen breath test positive Diagnosis: Secondary lactose intolerance Advice: She was advised to avoid dairy products and to take a tablet containing lactase in case she did eat any product containing milk.
  • 3. OBJECTIVES  Introduction and Definition  Isomerism in Sugars  Classification  Important Carbohydrates  Biomedical Importance of Carbohydrates
  • 4. INTRODUCTION  Hydrates of carbon  Saccharides — sugars  Some contain N and S  Synthesized in • Plants • Animals
  • 5. DEFINITION  Carbohydrates are polyhydroxylated compounds having at least 3 carbon atoms and a potentially active carbonyl group which may be an aldose or a ketose group.  Examples are: glucose, ribose.
  • 6. GLYCERALDEHYDE O C H HO C H CH2OH L-GLYCEROSE O C H H C OH CH2OH D-GLYCEROSE
  • 7. GLUCOSE H C O H C OH HO C H H C OH H C OH CH2OH GLUCOSE
  • 8.  ANOMERIC CARBON ATOM The carbon atom which is part of the carbonyl group Alpha(α) and Beta(β) anomers differ from each other only in respect to configuration around anomeric carbon atom.
  • 9. Alpha and Beta anomers of glucose H OH C H C OH HO C H O H C OH H C H C OH H α-D-GLUCOPYRANOSE HO H C H C OH HO C H O H C OH H C H C OH H β-D-GLUCOPYRANOSE
  • 10.
  • 11. ISOMERISM IN SUGARS  Isomers/Stereo-isomers: Compounds having the same chemical formulae but differing in the arrangement of their atoms in space and having different physical properties are called isomers.
  • 12. EPIMERS  Monosaccharides which differ in configuration around one specific C- atom are called epimers of one another  C-2 epimers • glucose and mannose  C-4 epimers • glucose and galactose
  • 13. H C O H C OH HO C H H C OH H C OH CH2OH D-GLUCOSE H C O HO C H HO C H H C OH H C OH CH2OH D-MANNOSE CARBON-2 EPIMERS
  • 14. CARBON-4 EPIMERS H C O H C OH HO C H H C OH H C OH CH2OH D-GLUCOSE H C O H C OH HO C H HO C H H C OH CH2OH D-GALACTOSE
  • 15. Carbohydrates Monosaccharides Oligosaccharides Derived Disaccharides Carbohydrates Aldoses Ketoses Oxidation Polysaccharides Reduction Amino sugars Homopolysaccharides Deoxy sugars Heteropolysaccharides CLASSIFICATION OF CARBOHYDRATES
  • 16. MONOSACCHARIDES No of C-atoms Potentially active carbonyl group Trioses Tetroses Pentoses Aldoses Ketoses Hexoses Heptoses “These carbohydrates cannot Octoses be hydrolyzed into simpler compounds”
  • 18.
  • 19. Reducing and Non-Reducing Sugars  Reduction is the chemist’s term for electron gain  A molecule that gains an electron is thus…… – “reduced”  A molecule that donates electrons is called a…… – “reducing agent”  A sugar that donates electrons is called a…… – “reducing sugar”  The electron is donated by the carbonyl group  Benedict’s reagent changes colour when exposed to a reducing agent
  • 20.
  • 21.
  • 22.
  • 23. Benedict’s Test  Benedict’s reagent undergoes a complex colour change when it is reduced  The intensity of the colour change is proportional to the concentration of reducing sugar present  The colour change sequence is: – Blue… – green… – yellow… – orange… – brick red
  • 24.
  • 25. The carbonyl group - monosaccharides  The carbonyl group is “free” in the straight chain form  But not free in the ring form  BUT remember – the ring form and the straight chain form are interchangeable  So all monosaccharides are reducing sugars  All monosaccharides reduce Benedict’s reagent
  • 26.
  • 27. The carbonyl group – disaccharides - sucrose  In some disaccharides e.g. sucrose both of the carbonyl groups are involved in the glycosidic bond  So there are no free carbonyl groups  Such sugars are called non-reducing sugars  They do NOT reduce Benedict’s reagent
  • 28.
  • 29. The carbonyl group – disaccharides - sucrose  The subunits of sucrose (glucose and fructose) are reducing sugars  If sucrose is hydrolysed the subunit can then act as reducing sugars  This is done in the lab by acid hydrolysis  After acid hydrolysis sucrose will reduce Benedict’s reagent
  • 30. OLIGOSACCHARIDES  These are the condensation products of 2 to 10 monosaccharide units  Disaccharides: These are the condensation products of two monosaccharide units e.g. sucrose, lactose.
  • 31. POLYSACCHARIDES  These are the condensation products of more than 10 molecules of monosaccharide units  They include starch, glycogen.  Stores of fuel  Structural elements of cells
  • 32. POLYSACCHARIDES Homopolysaccharides Heteropolysaccharides *Starch *Glycogen Glycoseaminoglycans *Cellulose Mucilages *Dextrins *Hyaluronic acid *Heparin *Agar *Chondoitin SO4 *Vegetable *Serum mucoids gums *Blood gp *Pectins polysaccharides *Hemicellulose
  • 33. DERIVED CARBOHYRATES Oxidation Reduction Amino Deoxy Products Products Sugars Sugars Gluconic acid Glycerol Glucosamine Glucuronic acid Ribitol Galactoseamine Glucaric acid Mannoseamine Deoxyribose “These are derived from carbohydrates by various chemical reactions”
  • 35. IMPORTANT CARBOHYDRATES  MONOSACCHARIDES  PENTOSES  Ribose:  Found in nucleic acids  Forms structural elements of nucleic acid and coenzymes  Intermediates of pentose phosphate pathway  ATP, NAD, NADP, flavoproteins etc
  • 36.  HEXOSES Glucose  Found in fruits, fruit juices, hydrolysis of starch, maltose and lactose.  Body sugar and the principal one used by the tissues  Excess in the blood is called hyperglycemia and presence in urine (glucosuria) indicates diabetes mellitus  Cataract due to sorbitol
  • 37. Fructose  Latin word for fruit — "fructus"  Found in fruit juices, honey  Released by the hydrolysis of inulin  Main nutritional source of energy for the spermatozoa and is found in the seminal fluid  Can be converted to glucose in the liver  It is the sweetest sugar  Lack of enzymes of metabolism can lead to essential fructosuria
  • 38. Galactose  Greek word for milk--"galact", found as a component of lactose in milk  Formed by the hydrolysis of lactose  Synthesized in the lactating mammary gland  Constituent of glycolipids and glycoproteins  Can be converted to glucose in the liver  Accumulation can lead to galactosemia and cataract (galactitol)
  • 39.
  • 40. OLIGOSACCHARIDES Sucrose  Known as table sugar  α-D-glucose ------ β-D- fructose  α-1 β-2 Sucrose α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside
  • 41. Lactose  Synthesized by lactating mammary gland  Milk sugar (lac-milk)  β-D-galactose β-D-glucose  β 1 4 linkage  Enzyme – lactase and lactose intolerance  Least sweet sugar – 16% of sucrose  Possesses one potential aldehyde group • reducing sugar • forms osazone crystals
  • 42. HOMOPOLYSACCHARIDES Starch  Main storage form of glucose in plants  Polysaccharide units • Amylose (20—28%) • Amylopectin 72—80%)  Polymer of α-D-glucose  α-1 4 glycosidic linkage  At branching points α-1 6 linkage  No free aldehyde group  Found in wheat, rice, corn, potatoes
  • 44. Form Linear Branch Linkage -1,4 (some -1,6) -1,4; - 1,6 Polymer units 200-2,000 Up to 2,000,000 Molecular weight Generally <0.5 million 50-500 million Gel formation Firm Non- gelling to soft Characteristics of Amylose and Amylopectin Characteristic Amylose Amylopectin
  • 45. Glycogen  Known as animal starch  Present in the liver and muscle  Both α-1 4 and α-1 6 linkages are found  More branched structure than starch  Gives red color with iodine
  • 47.
  • 48. A glycoside is an organic compound, usually of plant origin, that is composed of a sugar portion linked to a non-sugar moiety. The sugar portion is called glycone, while the non-sugar portion is c a l l e d a g l y c o n e . GLYCOSIDES
  • 49. The linkage between the sugar and the aglycone is an acetal linkage. Types of Glycosides : According to atoms involved in the glycosidic linkage: 1- O-glycosides 2- C-glycosides 3- S-glycosides 4- N-glycosides GLYCOSIDES
  • 50. GLYCOSIDES  Cardiac glycosides Digitalis useful in Congestive cardiac failure. They contain Steroid as aglycone.
  • 52. BIOMEDICAL IMPORTANCE  Glucose — most important carbohydrate  Glucose can be converted into • glycogen • ribose • galactose  Glycoproteins — molecular targeting  Antibodies and blood clotting factors  Structural components of cell membranes
  • 53.  Neuronal adhesion in development of nervous system (protein-glycan-heparan- sulfate)  Constituents of extra cellular matrix  Diseases associated with carbohydrates • Diabetes mellitus • Galactosemia • Lactose intolerance • Glycogen storage diseases