1. CARBOHYDRATES

2. Definition Polyhydroxy aldehyde, ketones and their derivatives.
C6 (H2O)6, C12 (H2O)11, C18 (H2O)16
Functions
Storage material for carbon and energy.

3. Concepts of Isomers C6 (H2O)6, C12 (H2O)11, C18 (H2O)16
Two or more different compounds which contain the same number and types of atoms and the same molecular weights.
 C6 (H2O)6, C12 (H2O)11, C18 (H2O)16
Projection formula:
Spatial arrangement to represent 3-dimensional structure

4. CHO H C OH CH OH CHO HO C H CH OH2
D-glyceraldehyde (Hydroxy group at the highest numbered asymmetric carbon atom is written to the right):
CHO HO C H CH OH 2
L-glyceraldehyde (Hydroxy group at the highest numbered asymmetric carbon atom is written to the left):
D-Erythrose is the mirror image of L-Erythrose.

5. Glyceraldehyde D-Glyceraldehyde L-Glyceraldehyde
Model Compounds of Monosaccharides
D-Glyceraldehyde L-Glyceraldehyde H O H O C C H C OH HO C H CH OH CH OH 2 2
D-Erythrose L-Threose H O H O C C H C OH H C OH H C OH HO C H CH OH CH OH 2 2

6. Mirror Image of GlucoseH H C O O C H C O H H O C H H O C H H C O H H C O H H O C H H C O H H O C H C H O H C H O H 2 2
L-glucose
D-glucose

7. Fisher Projection FormOH HO H C C C H C OH H C OH H C OH HO C H HO C H O HO C H O or H C OH H C OH H C OH H C OH H C H C CH OH CH OH CH OH 2 2 2
Anomeric Carbon --- The carbon atom which is involved in hemiacetal or acetal formation.

8. Mirror Image of GlucoseH H O H H O C C H C O H H O C H H O C H O O H C O H H C O H H O C H H C C H C H O H C H O H 2 2
- L-glucose
-D-glucose

9. Anomers Stereoisomers formed when ring is formed (a, b).C O CH 2 OH H HO or
a is same side with ring

10. Six and Five Member Ringso o
Furan
Pyran

11. Fisher & Harworth Projection FormsOH OH O HO CH 2 1 3 4 5 6 C H C OH HO C H O H C OH H C CH OH 2
a - D - Glucopyranose

12. a- and b- Glucose

13. a-Glucose b-Glucose

14. - L-glucose -D-glucose H H O H H O C C H C O H H O C H H O C H O O H2 2
- L-glucose
-D-glucose C H O H H 2 O O H H O H O H H C H O H 2 O H H H O H O H O H H H H O H O H H

15. MONOSACCHARIDES

16. Glucose a-D-Glucopyranose 6 CH O 5 4 1 HO OH 3 H OH C H C OH HO C H O2 1 3 4 5 6 C H C OH HO C H O H C OH H C CH OH 2
a-D-Glucopyranose

17. Fisher Projection FormHO C O CH 2 OH H a
-D-Glucopyranose
(35%) a
-D-Glucofuranose
(0.5%)
Aldehydo-D-glucose
(0.03%) b
-D-Glucofuranose
(0.5%) b
-D-Glucopyranose
(65%)

18. Galactose Component of lactose a-D-Galactopyranose CH OH HO O OH OH OH2 HO O OH OH OH
a-D-Galactopyranose

19. Fructose D-Fructose b-D-Fructose a-D-Fructose CH OH CH OH CH OH HO OH2 HO 2 2 OH C O C C HO C H HO C H HO C H O or O H C OH H C OH H C OH H C OH H C H C CH OH CH OH CH OH 2 2 2
D-Fructose b-D-Fructose a-D-Fructose

20. Naturally-occurring free form
Fructose
HOCH O
HOCH CH OH 2 OH O 2 2 HO HO CH OH 2 OH OH OH
b - D - Fructofuranose a - D - Fructofuranose O OH CH 2 H C HO
Naturally-occurring free form

21. Anydrides of 2 monosaccharides
Disaccharide
Anydrides of 2 monosaccharides

22. Linkage of Monosaccharides

23. Maltose 4-0-a-D-Glucopyranosyl- a-D-Glucopyranose CH OH CH OH O O OH2 2 O O OH OH HO O OH OH OH

24. Cellobiose 4-0-b-D-Glucopyranosyl -b-D-Glucopyranose CH OH CH OH O O2 2 O O OH O OH OH HO OH OH

25. 2-0-a-D-Glucopyranosyl b-D-Fructofuranoside
Sucrose
2-0-a-D-Glucopyranosyl b-D-Fructofuranoside O OH HO CH 2 H 1 5 2 3 4 6
Invert sugar is the hydrolyzed sucrose into glucose and fructose.

26. Lactose Principal sugar in milkCH OH CH OH 2 2 OH O O O OH OH OH OH OH
4-0-b-D-Galactopyranosyl-a-D- Glucopyranose
4-0-b-D-Galactopyranosyl-b-D-Glucopyranose

27. Relative Sweetnes of Sugars
Sucrose 100
Glucose 74
Fructose 174
Lactose 16
Invert Sugar 126
Maltose 32
Galactose 32

28. Oligosaccharides

29. Raffinose
6-0-a-D-Galactopyranosyl-2-0-a-D-Glucopyranosyl -b-D-Fructofuranoside

30. Stachyose 6-0-a-D-Galactopyranosyl-6-0-a-D-Galactopyranosyl
-2-0-a-D-Glucopyranosyl-b-D-Fructofuranoside
“Flatulence Factor” CH OH 2 OH O CH 2 CH O O OH 2 OH O O CH OH O OH 2 OH OH HO OH OH O CH OH 2 OH OH

31. Polysaccharides

32. Cellulose Polymer of b-D-Glucose (1, 4) linkage.
Repeating cellobiose moiety. O OH CH 2 n

33. Cellulose

34. Starch
The reserve carbohydrate of plants. Occurs as granules in the cell.
Made of amylose and amylopectin.
Amylose --- Polymer of a-D- Glucose (1->4) linkage-straight-chain.

35. Amylose

36. Amylopectin
Polymer of a-D-Glucose (1->4) linkage in addition to a-D-Glucose (1->6) linkage.
The length of linear units in amylopectin is only 25.
a-(1->4) linkage (25) to a-(1->6) linkage.

37. Amylose and Amylopectin

38. Glycogen Animal starch.
a - (1 -> 4) linkage and a - (1 -> 6) linkage :

39. Glycogen

40. Glycogen

41. Pectin
Polymer of 4-0-a-D-Galacturonic acid (1 4) & Methylgalacturonate
COOH
COOCH
COOCH
COOH 3 3 OH O O O O O O O O O OH OH OH OH OH OH OH OH OH OH OH OH

42. Degree of Methylation (DM)
The higher the degree of methylation, the higher the temperature at which the gel forms.
For gel formation at least 50% of the carboxyl group are methylated. Pectin (about 74 DM) is used in jams. For jellies DM is about 60.

43. Functions of Carbohydrates

44. Functions of Polysaccharides
1. Viscosity control
2. Texture control
3. Emulsifying agent
4. Water-binding capacity
5. Stabilizer

45. Corn Syrup
Enzyme
Corn Starch
Corn Syrup + H
High Glucose D
Maltose
Dextrose
Gram of Reducing Sugar
Dextrose Equivalent (DE) =
x 100
Gram of Total Sugar
The higher the DE, generally the greater the glucose content in corn syrup.

46. Amylose

47. High Fructose Syrups Generally: Glucose 50% Fructose 42% Maltose 1.5%
Glucose Isomerase
Glucose in Syrup
Fructose
Generally: Glucose 50%
Fructose 42%
Maltose 1.5%
Isomaltose 1.5%
Higher Saccharides 5.0%

48. Corn Syrup High Maltose Syrup Low DE High DE Glucose 9 14 43 Maltose
High Maltose Syrup
Low DE
High DE %
Glucose 9 14 43
Maltose 52 12 32
Triose 13 10 3
Tetrose 2 9 5
Pentose 24 55 12

49. Modified Starches

50. Amylose

51. Modified Starches
1.  Pregelatinized Starch --- Precooked and roll dried starch to give product that readily disperses in cold water.
2.  Thin-boiling or Acid-modified Starch --- Suspended granular starch in a very dilute acid under somewhat below its gelatinization temperature.
3. Oxidized Starches --- Oxidation of starch with alkaline hypochloride to get -COOH at C6.

52. Amylose

53. Carbohydrate Determination

54. Determination 1. Monosaccharides and Oligosaccharides
A. Enzymatic Method
1. Glucose oxidase
2. Hexokinase
B. Chromatography Method
1. Thin layer chromatography
2. Gas chromatography
3. Liquid column chromatography
2. Polysaccharides

55. a- and b- Glucose

56. Glucose Oxidase System
D-Glucose O Gluconic Acid H2O2   
H2O Dianisidine H2O + Oxidized 0-Dianisidine
(Colorless) (Brown)
Glucose Oxidasse
Peroxidase

57. Gluconic Acid, Glucouronic Acid and GluconolactoneH O O O O H C C H C O H H C O H H H O C H H O C H O H + H C O H H C O H H H C H C O H C H O H C H O H 2 2
Gluconic Acid
Glucouronic Acid
Gluconolactone

58. Hexokinase System Glucose + ATP G - 6 - P + ADP
G P + NADP Gluconate phosphate NADPH H+
Hexokinase
G-6-P DH
G-6-P DH: Glucose-6-phosphate dehydrogenase
NADP+ : Nicotinamide Adenine Dinucleotide Phosphate
NADPH : Reduced Nicotinamide Adenine Dinucleotide Phosphate
The NADPH formed in this reaction is stoichiometric with the amount of glucose.
NADPH is measured at 334 nm.

59. G-6-Phosphate + NADP+ Gluconate-6-phosphate + NADPH + H2 P H C O 2 P + + +
NAPD+
NADPH + H

60. NADP + C O N H 2 O - N + O P O C H 2 O O H O H O N H 2 N N N N - O P O
PO3H2

61. NADPH - - + H+ CONH2 H N O O P O C H O O H O H O N H N N N N O P O C H
PO3H2

62. Qualitative Analysis Thin Layer chromatography
Silica gel as stationary phase
Quantitation by densitomer
Solvent
For Spot A C A B
Rf = S S A B A

63. Gas Chromatography Ether linkage Trimethyl chlorosilane
Requirement: Compounds must be volatile.
Sugars form Trimethylsilyl Ether.
Ether linkage Trimethyl chlorosilane

64. Derivation of Glucose with TrimethylchlorosilaneOH O HO CH 2 1 3 4 5 6 Si CH 3
5Cl +
Glucose
Trimethylchlorosilane 6 CH
O-Si(CH3)3 2 O 5 +
5HCl 4 1
O-Si(CH3)3
(CH3)3-Si-O
O-Si(CH3)3 3 2
O-Si(CH3)3

65. Liquid Chromatography
Stationary Phase: Waters Associates
Solvent: H2O/CH3CN

66. Polysaccharides
Quantification depends on chemical or enzymatic hydrolyses of them into monomers and analysis of the monomers.
Qualitative Analyses
1. Amylose I Blue color
Use spectrometer for determining the amylose - iodine blue color
2. Amylopectin + I Reddish color

67. Summary