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CARBOHYDRATES

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CARBOHYDRATES OXIDATION PRODUCTS (SUGAR ACIDS) When oxidized under proper conditions, Aldoses may form three types of acids (Sugar Acids): Uronic Acids. – PowerPoint PPT presentation

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Title: CARBOHYDRATES


1
CARBOHYDRATES
2
LECTURE OUTLINE
  • By the end of the lecture, the student should
    know
  • The Importance of carbohydrates.
  • The Definition of Carbohydrates.
  • The Classification of Carbohydrates.
  • The Difference between various Isomers..

3
CARBOHYDRATE IMPORTANCE
  • Most Abundant Class of Biomolecules.
  • An Important Macronutrient.
  • Performs important physiological functions in the
    body.
  • Associated with Pathological Conditions (Diabetes
    Mellitus, Lactose Intolerance).

4
DEFINING CARBOHYDRATES
  • Carbohydrates or Saccharides(Greek Sakcharon
    meaning "Sugar")
  • Organic compounds composed of Carbon, Hydrogen
    and oxygen.
  • Many Carbohydrates also contain Nitrogen and
    other elements.

5
  • Carbohydrates derive their name from a Misleading
    Concept'Hydrates of Carbon
  • Hydrogen and Oxygen in Carbohydrates were found
    to be present in the same proportion as in water.
    (21).(E.g. Glucose C6H12O6 or C6 (H2O)6).
  • It is due to this fact that compounds derived
    their name Carbon Hydrate.

6
GLUCOSE
  • H-CO
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • H-C-OH
  • ?
  • CH2OH

7
  • This term is not a perfect derivation as many
    carbohydrates do not have the same proportion as
    water.
  • Example DEOXYRIBOSE (C5H10O4)
  • H-CO
  • ?
  • H-C-H
  • ?
  • H-C-OH
  • ?
  • H-C-OH
  • ?
  • CH2OH

8
CHEMICAL DEFINITION OF CARBOHYDRATES
  • Polyhydroxyl Having more than one hydroxyl
    group.
  • (-OH)
  • Functional Group It is a specific group of atoms
    or bonds which are part of a larger hydrocarbon
    chain.(Provide a specific chemical behaviour).

9
  • For carbohydrates, the functional group is the
    carbonyl group which may be either
  • Aldehyde Group (H-CO)
  • Or
  • Keto Group (CO)

10
WHAT IS SIMILAR DIFFERENTIN THESE TWO
STRUCTURES?
  • H-CO
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • CH2OH
  • ?
  • CO
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • CH2OH

More than one hydroxyl group in both

11
WHAT IS COMMON DIFFERENTIN THESE TWO
STRUCTURES?
  • H-CO
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • CH2OH
  • ?
  • CO
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • CH2OH

Carbonyl Group in both But?

12
What is common differentin these two
Structures?
  • H-CO
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • CH2OH
  • ?
  • CO
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • CH2OH

Aldehyde in 1 and Ketone in 2

13
  • Carbohydrates arePolyhydroxy Alcoholswith
    Carbonyl groupsWhich May Either BeAldehyde
    (H-CO) orKeto (CO) Groups.

14
Can you Visualize Either AldehydeOrKetone Group
In This Polyhydroxy Alcohol?
15
No! But Hydrolysis of This Compound Yields Two
Compounds with Aldehyde Or Ketone Groups
HOH
16
No! But Hydrolysis of This Compound Yields Two
Compounds with Aldehyde Or Ketone Groups


H
-
C



CH
OH

O
HOH
2
½
½
O








O

C




H
-
C
-
OH

½
½








OH
-
C
-
H

OH
-
C
-
H

½
½










H
-
C
-
OH



H
-
C
-
OH

½
½










H
-
C
-
OH




H
-
C
-
OH

½
½










CH
OH



CH
OH

2
2

17
Many Polyhydroxy Alcohols may Not have an active
Aldehyde or Ketone Group But they May YieldThem
On Hydrolysis. They Are Also Designated as
Carbohydrates.
18
THEREFORE, THE COMPLETE DEFINITION OF
CARBOHDRATES IS
  • CARBOHYDRATES ARE POLYHYDROXYL ALCOHOLS WITH
    POTENTIALLY ACTIVE CARBONY GROUPS WHICH MAY BE
    EITHER AN ALDEHYDE OR KETONE GROUP. THEY ALSO
    CONTAIN THOSE COMPOUNDS, WHICH YIELD THEM ON
    HYDROLYSIS.

19
Classification of carbohydrates
  • Carbohydrates are mainly classified into four
    different groups
  • Monosachharides
  • Disaccharides
  • Oligosaccharides
  • Polysaccharides

20
MONOSACCHARIDES
  • Monosaccharides are those carbohydrates which
    Cannot be Hydrolyzed further into more simple
    carbohydrates.
  • Thus, they are the Simplest form of
    Carbohydrates.
  • Familiar examples are
  • Glucose, Fructose, Ribose Galactose.

21
Monosaccharides are further classified on the
basis of
  • Aldehyde or Ketone Group
  • Aldomonosaccharides (Aldoses).
  • Ketomonosaccharides (Ketoses).
  • Carbon Chain Length.
  • Trioses.
  • Tetroses.
  • Pentoses.
  • Hexoses.
  • Heptoses.

22
CARBONYL GROUP
H-CO ? H-C-OH ? OH-C-H
? H-C-OH ? H-C-OH ?
CH2OH
CH2OH ? CO ? OH-C-H
? H-C-OH ? H-C-OH ?
CH2OH
?GLUCOSE FRUCTOSE--gt
23
CARBON CHAIN
H-CO ? H-C-OH ? OH-C-H
? H-C-OH ? H-C-OH ?
CH2OH
H-CO ? OH-C-H ? H-C-OH
? H-C-OH ? CH2OH
?GLUCOSE ARABINOSE--gt
24
EXAMPLES OF MONOSACCHARIDES
NO. OF CARBON ATOMS ALDO KETO
3C TRIOSE GLYCERALDEHYDE DIHYDROXYACETONE
4C TETROSE ERYTHROSE ERYTHRULOSE
5C PENTOSE RIBOSE, XYLOSE RIBULOSE, XYLULLOSE
6C HEXOSE GLUCOSE, GALACTOSE, MANNOSE FRUCTOSE
25
glyceraldehyde
26
  • GLYCERALDEHYDE IS THE SIMPLEST MONOSACCHARIDE(PART
    ICULARLY ALDOSES)
  • IT CANNOT BE HYDROLYZED FURTHER.
  • IT IS THE SMALLEST POSSIBLE STRUCTURE THAT IS A
    CARBOHYDRATE CANNOT HAVE LESS THAN 3 CARBON
    ATOMS.
  • GENERAL FORMULA OF MONOSACCHARIDE (CH2O)N
  • (WHERE N IS ANY NUMBER OF THREE OR GREATER)

27
isomerism
  • Isomers are basically molecules that have the
    same chemical formula but they differ in their
    chemical structures.
  • Asymmetric Carbon is an important determinant of
    Isomerism.
  • Asymmetric Carbon is that Carbon which is
    attached with four different groups.

28
Straight Chain Structure of Typical
Monosaccharide (Glucose)
29
The assignment of D or L is made according to the
orientation of the Penultimate Carbon
If the Hydroxyl Group is on the right the
molecule is a D sugar, Otherwise It is an L sugar.
L-Sugar D-Sugar
30
D and L isomerism produce mirror images
31
epimerism
  • Isomers which differ from each other only with
    regard to oh group on a single asymmetric carbon
    atom.

32
Optical isomers
  • When a beam of polarized light is passed through
    sugars, they will be rotated either towards right
    or left.
  • Right Rotation (dextrorotatory) E.g. D- Glucose
  • Left Rotation (levorotatory) E.g. D-Fructose

33
Monosaccharide Derivatives of Biological
Importance
  • Oxidation Products (Sugar Acids)
  • Reduction Products (Sugar Alcohols).
  • Amino Sugars.
  • Sugar Phosphates.

34
Oxidation Products (Sugar Acids)
  • When oxidized under proper conditions, Aldoses
    may form three types of acids (Sugar Acids)
  • Uronic Acids.
  • Aldonic acids.
  • Saccharic Acids.
  • Type of sugar Acid produced depends on which
    carbon is oxidized.

35
Uronic Acid
H-CO ? H-C-OH ? OH-C-H
? H-C-OH
? H-C-OH ? CH2OH
  • Oxidation Of Aldose
  • At Primary Alcohol
  • (Terminal Carbon)

COOH
36
Aldonic Acid
COOH
  • H-CO
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • Oxidation Of Aldose At
  • Carbonyl Carbon
  • (Aldehyde Group)

37
Saccharic Acid
COOH
  • H-CO
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • Oxidation Of Aldose
  • At Both Aldehyde
  • Terminal Carbons

COOH
38
Examples of Aldoses with their Corresponding
Uronic Acids are
  • Sugar
  • Glucose
  • -------------
  • Mannose
  • -------------
  • Galactose
  • -------------
  • Uronic Acids
  • Glucuronic acid,
  • Iduronic acid
  • ----------------------
  • Mannuronic acid
  • ----------------------
  • Galacturonic acid
  • ------------------------

39
Examples of Aldoses with their Corresponding
Aldonic Acids are
  • Sugar
  • Glucose
  • -------------
  • Mannose
  • -------------
  • Galactose
  • -------------
  • Aldonic Acids
  • Gluconic acid
  • ----------------------
  • Mannonic acid
  • ----------------------
  • Galactonic acid
  • ------------------------

40
Amino Sugar
  • Substitution of Amino Group for a Hydroxyl Group
    of a Sugar Results in the Formation of an Amino
    Sugar.
  • The Amino Group is attached to Carbon 2.

H-CO ? H-C-OH ? OH-C-H
? H-C-OH
? H-C-OH ? CH2OH
NH2
41
Common Examples of Amino Sugars (Aminosaccharides)
  • Galactosamine
  • Glucosamine

42
Sugar Alcohols Reduction Products
  • Sugar Alcohols are obtained by reduction of
    Monosaccharides (Both Aldoses and Ketoses) and
    disaccharides.
  • Sugar alcohols, also known as Polyols, Polyhydric
    Alcohols, or Polyalcohols.

43
Sugar Alcohols are the Hydrogenated forms of the
Aldoses or Ketoses
  • H- CO H2
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • Glucose
  • CH2OH
  • ?
  • H-C-OH
  • ?
  • OH-C-H
  • ?
  • H-C-OH
  • ?
  • H-C-OH
  • ?
  • CH2OH
  • Sorbitol

44
Sugars with their Corresponding Alcohols
  • Glyceraldehyde
  • Dihydroxyacetone
  • Glucose
  • Mannose
  • Fructose
  • Galactose
  • Ribose
  • Erythrose
  • Xylose
  • Lactose
  • Maltose
  • Glycerol
  • Sorbitol (Glucitol)
  • Mannitol
  • Sorbitol Mannitol
  • Dulcitol
  • Ribitol
  • Erythritol
  • Xylitol
  • Lactitol
  • Maltitol

45
Sugar Phosphates
  • Phosphate Esters formed by various
    Monosaccharides are of Great Importance in
    Metabolic Reactions.
  • Sugar phosphates of biological importance.
  • Ribose and Deoxyribose in Nucleic Acids are
    Phosphate Esters of these monosaccharides.
  • Phosphates of Glucose, Fructose and
    Glyceraldehyde etc. are important intermediate
    compounds in carbohydrate metabolism of almost
    all the cells.

46
Disaccharides
  • Two Joined Monosaccharides.
  • Sucrose Glucose Fructose
  • Maltose Glucose Glucose
  • Lactose Glucose Galactose

47
Oligosaccharides
  • Composed Of
  • Three To Ten Monosaccharide Units.
  • E.g. Fructooligosaccharides 

48
Polysaccharides
  • Larger Than Ten Monosaccharide Units.
  • Can Reach Many Thousands Of Units.
  • Homopolysaccharides.
  • Heteropolysaccharides.

49
Homopolysaccharides
  • Similar Types of Monosaccharide Units.
  • Starch
  • Glycogen
  • Cellulose

50
Heteropolysaccharides
  • Different Types of Monosaccharide Units.
  • Mucopolysaccharides (Glycosaminoglycans that
    contain galactose and amine sugars)
  • Agar (Contains various sugars like Glucose,
    Galactose)
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