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Chemistry of carbohydrates
Mohd Asad Farooqi
Lecturer
Mahrishi College Of
Pharmacy1/7/2021 1
Introduction
Carbohydrates (or saccharides) consist of only carbon, hydrogen
and oxygen
Carbohydrates come primarily from plants, however animals can
also biosynthesize them
Energy from the sun is stored in plants, which use photosynthesis
to convert carbon dioxide and water to glucose and oxygen
In the reverse process, energy is produced when animals oxidize
glucose during respiration
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Definition
Carbohydrates โ€“ poly hydroxy aldehydes or poly
hydroxy-ketones of formula (CH2O)n, or
compounds that can be hydrolyzed to them.
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FUNCTION OF CARBOHYDRATE
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Types of carbohydrates
Monosaccharidesโ€“carbohydrates that cannot be
hydrolyzed to simpler carbohydrates; eg. Glucose or
fructose.
Disaccharidesโ€“carbohydrates that can be hydrolyzed
into two monosaccharide units; eg. Sucrose, which is
hydrolyzed into glucose andfructose.
Oligosaccharidesโ€“carbohydrates that can be
hydrolyzed into a few monosaccharideunits.
Polysaccharides โ€“ carbohydrates that are polymeric
sugars; eg Starch orcellulose.
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PROPERTIES OF CARBOHYDRATE
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CONT....
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Classification of Monosaccharides
Monosaccharides have 3-8 carbons in a chain, with one carbon in
a carbonyl group, and the other carbons attached to c groups
- An aldose has the carbonyl C1 (an aldehyde)
- A ketose has the carbonyl on C2 (a ketone)
-The number of carbons is indicated as follows: triose (3 Cโ€™s),
tetrose (4 Cโ€™s), pentose (5 Cโ€™s), hexose(6 Cโ€™s)
CH2OH
O
H OH
H OH
H OH
H OH
CH2OH
O
HO H
H OH
H OHH OH
H O
H O
CH2OH
Glyceraldehyde
(aldotriose)
CH2OH
Erythrulose
(ketotetrose)
CH2OH
Ribose
(aldopentose)
CH2OH
Fructose
(ketohexose)
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Aldoses and ketoses
Ketoses (e.g., fructose)
have a keto group, usually
at C2.
Aldoses (e.g., glucose)have
an aldehyde group at one
end.
H O
C
H C OH
HO C H
H C OH
H C OH
CH2OH
D-glucose
CH2OH
C O
HO C H
H C OH
H C OH
CH2OH
D-fructose
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Monosaccharides
Monosaccharides are classified by their numberof
carbon atoms
Trios e
Tetrose
Pentose
Hexose
Heptose
Octose
FormulaName
C3 H6 O3
C4 H8 O4
C5 H1 0 O5
C6 H1 2 O6
C7 H1 4 O7
C8 H1 6 O8
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Three Important Monosaccharides
D-Glucose is the most common monosaccharide
- Primary fuel for our cells, required for many tissues
- Main sources are fruits, vegetables, corn syrup and honey
- Blood glucose is maintained within a fairly small range
- Some glucose is stored as glycogen, excess is stored as fat
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D-Galactose comes from hydrolysis of the disaccharide
lactose
- Used in cell membranes of central nervous system
-Converted by an enzyme into glucose for respiration(lack
of this enzyme causes galactosemia, which can cause
retardation in infants if not treated by complete removal
from diet)
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D-Fructose is the sweetest carbohydrate
- Converted by an enzyme into glucose for respiration
- Main sources are fruits and honey
- Also obtained from hydrolysis of the disaccharide sucrose
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Amino Sugars
Amino sugars contain an -NH2 group in place of an -
OH group
๏‚ก only three amino sugars are common in nature:D-glucosamine,
D-mannosamine, and D-galactosamine
CHO
H NH2
HO H
H OH
H OH
CHO
H NHCCH3
HO H
H OH
H OH
CHO OCHO
H NH2
HO H
HO4 H
H OH
H2 N 2 H
HO H
H OH
H OH
CH2OH
D-Mannosamine
(C-2 stereoisomer
of D-glucosamine
CH2OH
D-Glucosamine
CH2OH
D-Galactosamine
(C-4 stereoisomer
of D-glucosamine)
CH2OH
N-Acetyl-D-
glucosamine
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Reducing sugar โ€“ a carbohydrate that is oxidizedby Tollenโ€™s,
Fehlingโ€™s or Benedictโ€™s solution.
Tollenโ€™s: Ag+ ๏‚’ Ag (silver mirror)
Fehlingโ€™s or Benedictโ€™s: Cu2+ (blue) ๏‚’ Cu1+ (red
ppt)
These are reactions of aldehydes and alpha-hydroxyketones.
All monosaccharides (both aldoses and ketoses) and most*
disaccharides are reducing sugars.
*Sucrose (table sugar), a disaccharide, is not a reducing sugar.
Identification tests
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Disorders of carbohydrate metabolism
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Diabetes mellitus (DM),
Diabetes mellitus (DM), commonly known as diabetes, is a group of metabolic
disorders characterized by a high blood sugar level over a prolonged period of
time.Symptoms often include frequent urination, increased thirst, and increased
appetite.
If left untreated, diabetescan cause Many complications.Acutecomplications can
includediabetic ketoacidosis, hyperosmolar hyperglycemic state, or death.
Serious long-term complications include cardiovascular disease, stroke, chronic
kidney disease, foot ulcers, damage to the nerves, damage to the eyes and cognitive
impairment.
Diabetes is due to either the pancreas not producing enough insulin, or the cells of
the body not respondingproperlyto the insulin produced.There are three main types
of diabetesmellitus.
1/7/2021 45
Lactose intolerance
Lactose intolerance is a decreased ability to digest lactose, a sugar
found in dairyproducts.
Those affected vary in the amount of lactose they can tolerate before
symptoms develop.
Symptoms may include abdominal pain, bloating, diarrhea, gas,
and nausea.These symptoms typically start thirty minutes to two hours
after eating or drinking milk-based food. Their severity typically
depends on the amount a person eats or drinks.
Lactose intolerance does not cause damage to the gastrointestinal tract.
1/7/2021 46
Galactosemia
Galactosemia (British galactosaemia, from
Greek ฮณฮฑฮปฮฑฮบฯ„ฯŒฮถฮท + ฮฑฮฏฮผฮฑ, meaning galactose + blood, accumulation
of galactose in blood) is a rare genetic metabolic disorder that affects
an individual's ability to metabolize the sugar galactose properly.
Galactosemia follows an autosomal recessive mode of inheritance that
confers a deficiency in an enzyme responsible for adequate galactose
degradation.
Its incidence is about 1 per 60,000 births for people of European
ancestry. In other populations the incidence rate differs. Galactosaemia
is about one hundred times more common (1:480 births) in the Irish
Traveller population.
1/7/2021 47
Glycogen storage disease (GSD
A glycogen storage disease (GSD,
also glycogenosis and dextrinosis) is a metabolic disorder caused
by enzyme deficiencies affecting either glycogen synthesis, glycogen
breakdown or glycolysis (glucose breakdown), typically
in muscles and/or liver cells.
GSD has two classes of cause: genetic and acquired. Genetic GSD is
caused by any inborn error of metabolism (genetically
defective enzymes) involved in these processes. In livestock,
acquired GSD is caused by intoxication with
the alkaloid castanospermine.
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Carbohydrate( classification,strucure, properties, qualitative test, disease

  • 1. Chemistry of carbohydrates Mohd Asad Farooqi Lecturer Mahrishi College Of Pharmacy1/7/2021 1
  • 2. Introduction Carbohydrates (or saccharides) consist of only carbon, hydrogen and oxygen Carbohydrates come primarily from plants, however animals can also biosynthesize them Energy from the sun is stored in plants, which use photosynthesis to convert carbon dioxide and water to glucose and oxygen In the reverse process, energy is produced when animals oxidize glucose during respiration 1/7/2021 2
  • 3. Definition Carbohydrates โ€“ poly hydroxy aldehydes or poly hydroxy-ketones of formula (CH2O)n, or compounds that can be hydrolyzed to them. 1/7/2021 3
  • 8. Types of carbohydrates Monosaccharidesโ€“carbohydrates that cannot be hydrolyzed to simpler carbohydrates; eg. Glucose or fructose. Disaccharidesโ€“carbohydrates that can be hydrolyzed into two monosaccharide units; eg. Sucrose, which is hydrolyzed into glucose andfructose. Oligosaccharidesโ€“carbohydrates that can be hydrolyzed into a few monosaccharideunits. Polysaccharides โ€“ carbohydrates that are polymeric sugars; eg Starch orcellulose. 1/7/2021 8
  • 12. Classification of Monosaccharides Monosaccharides have 3-8 carbons in a chain, with one carbon in a carbonyl group, and the other carbons attached to c groups - An aldose has the carbonyl C1 (an aldehyde) - A ketose has the carbonyl on C2 (a ketone) -The number of carbons is indicated as follows: triose (3 Cโ€™s), tetrose (4 Cโ€™s), pentose (5 Cโ€™s), hexose(6 Cโ€™s) CH2OH O H OH H OH H OH H OH CH2OH O HO H H OH H OHH OH H O H O CH2OH Glyceraldehyde (aldotriose) CH2OH Erythrulose (ketotetrose) CH2OH Ribose (aldopentose) CH2OH Fructose (ketohexose) 1/7/2021 12
  • 23. Aldoses and ketoses Ketoses (e.g., fructose) have a keto group, usually at C2. Aldoses (e.g., glucose)have an aldehyde group at one end. H O C H C OH HO C H H C OH H C OH CH2OH D-glucose CH2OH C O HO C H H C OH H C OH CH2OH D-fructose 1/7/2021 23
  • 24. Monosaccharides Monosaccharides are classified by their numberof carbon atoms Trios e Tetrose Pentose Hexose Heptose Octose FormulaName C3 H6 O3 C4 H8 O4 C5 H1 0 O5 C6 H1 2 O6 C7 H1 4 O7 C8 H1 6 O8 1/7/2021 24
  • 25. Three Important Monosaccharides D-Glucose is the most common monosaccharide - Primary fuel for our cells, required for many tissues - Main sources are fruits, vegetables, corn syrup and honey - Blood glucose is maintained within a fairly small range - Some glucose is stored as glycogen, excess is stored as fat 1/7/2021 25
  • 26. D-Galactose comes from hydrolysis of the disaccharide lactose - Used in cell membranes of central nervous system -Converted by an enzyme into glucose for respiration(lack of this enzyme causes galactosemia, which can cause retardation in infants if not treated by complete removal from diet) 1/7/2021 26
  • 27. D-Fructose is the sweetest carbohydrate - Converted by an enzyme into glucose for respiration - Main sources are fruits and honey - Also obtained from hydrolysis of the disaccharide sucrose 1/7/2021 27
  • 33. Amino Sugars Amino sugars contain an -NH2 group in place of an - OH group ๏‚ก only three amino sugars are common in nature:D-glucosamine, D-mannosamine, and D-galactosamine CHO H NH2 HO H H OH H OH CHO H NHCCH3 HO H H OH H OH CHO OCHO H NH2 HO H HO4 H H OH H2 N 2 H HO H H OH H OH CH2OH D-Mannosamine (C-2 stereoisomer of D-glucosamine CH2OH D-Glucosamine CH2OH D-Galactosamine (C-4 stereoisomer of D-glucosamine) CH2OH N-Acetyl-D- glucosamine 1/7/2021 33
  • 36. Reducing sugar โ€“ a carbohydrate that is oxidizedby Tollenโ€™s, Fehlingโ€™s or Benedictโ€™s solution. Tollenโ€™s: Ag+ ๏‚’ Ag (silver mirror) Fehlingโ€™s or Benedictโ€™s: Cu2+ (blue) ๏‚’ Cu1+ (red ppt) These are reactions of aldehydes and alpha-hydroxyketones. All monosaccharides (both aldoses and ketoses) and most* disaccharides are reducing sugars. *Sucrose (table sugar), a disaccharide, is not a reducing sugar. Identification tests 1/7/2021 36
  • 44. Disorders of carbohydrate metabolism 1/7/2021 44
  • 45. Diabetes mellitus (DM), Diabetes mellitus (DM), commonly known as diabetes, is a group of metabolic disorders characterized by a high blood sugar level over a prolonged period of time.Symptoms often include frequent urination, increased thirst, and increased appetite. If left untreated, diabetescan cause Many complications.Acutecomplications can includediabetic ketoacidosis, hyperosmolar hyperglycemic state, or death. Serious long-term complications include cardiovascular disease, stroke, chronic kidney disease, foot ulcers, damage to the nerves, damage to the eyes and cognitive impairment. Diabetes is due to either the pancreas not producing enough insulin, or the cells of the body not respondingproperlyto the insulin produced.There are three main types of diabetesmellitus. 1/7/2021 45
  • 46. Lactose intolerance Lactose intolerance is a decreased ability to digest lactose, a sugar found in dairyproducts. Those affected vary in the amount of lactose they can tolerate before symptoms develop. Symptoms may include abdominal pain, bloating, diarrhea, gas, and nausea.These symptoms typically start thirty minutes to two hours after eating or drinking milk-based food. Their severity typically depends on the amount a person eats or drinks. Lactose intolerance does not cause damage to the gastrointestinal tract. 1/7/2021 46
  • 47. Galactosemia Galactosemia (British galactosaemia, from Greek ฮณฮฑฮปฮฑฮบฯ„ฯŒฮถฮท + ฮฑฮฏฮผฮฑ, meaning galactose + blood, accumulation of galactose in blood) is a rare genetic metabolic disorder that affects an individual's ability to metabolize the sugar galactose properly. Galactosemia follows an autosomal recessive mode of inheritance that confers a deficiency in an enzyme responsible for adequate galactose degradation. Its incidence is about 1 per 60,000 births for people of European ancestry. In other populations the incidence rate differs. Galactosaemia is about one hundred times more common (1:480 births) in the Irish Traveller population. 1/7/2021 47
  • 48. Glycogen storage disease (GSD A glycogen storage disease (GSD, also glycogenosis and dextrinosis) is a metabolic disorder caused by enzyme deficiencies affecting either glycogen synthesis, glycogen breakdown or glycolysis (glucose breakdown), typically in muscles and/or liver cells. GSD has two classes of cause: genetic and acquired. Genetic GSD is caused by any inborn error of metabolism (genetically defective enzymes) involved in these processes. In livestock, acquired GSD is caused by intoxication with the alkaloid castanospermine. 1/7/2021 48