Carbohydrate presentation

1. CARBOHYDRATES
By-Sanju Sah
St. Xavier’s college, Maitighar, Kathmandu
Department of Microbiology

2. Carbohydrates
• Carbohydrates are the most abundant organic
molecules in nature.
• They are primarily composed of the elements carbon,
hydrogen and oxygen.
• The name carbohydrate literally means 'hydrates of
carbon'.
• Some of the carbohydrate possess the empirical
formula (CH2O)n .
• However,
compounds
there are several non-carbohydrate
(e.g. acetic acid, lactic acid,) which also
appear as hydrates of carbon.

3. carbohydrates (e.g.
do not satisfy the
• Further, some of the genuine
Rhamnohexose, deoxyribose,)
general formula.
• Hence carbohydrates cannot be always considered
as hydrates of carbon.
• Carbohydrates may be defined as
polyhydroxyaldehydes or ketones or compounds
carbohydrates
which produce them on hydrolysis.
• The term 'sugar' is applied to
soluble in water and sweet to taste.

4. Functions of carbohydrates
• Carbohydrates participate in a wide range of functions
1. They are the most abundant dietary source of energy
(a Cal/g) for all organisms.
2. Carbohydrates are precursors for many organic
compounds (fats, amino acids).
3. Carbohydrates (as glycoproteins and glycolipids)
participate in the structure of cell membrane and
cellular functions such as cell growth, adhesion and
fertilization.
4. They are structural components of many organisms.
These include the
exoskeleton of some
fiber (cellulose) of plants,
insects and the cell wall of
microorganisms.
5. Carbohydrates also serve as the storage form of energy
(glycogen) to meet the immediate energy demands of
the body.

5. CLASSIFICATION OF CARBOHYDRATES
• Carbohydrates are often referred to as
saccharides (Greek: sakcharon-sugar).
• They are broadly classified into three major
groups- monosaccharides, oligosaccharides and
polysaccharides.
• This categorization is based on the number of
sugar units.
• Mono- and oligo-saccharides are sweet to taste,
crystalline in character and soluble in water, hence
thev are commonly known as sugar

6. Monosaccharides
• Monosaccharides (Greek : mono-one) are the simplest
group of carbohydrates and are often referred to as simple
sugars.
• They have the general formula Cn(H20)n, and they cannot be
further hydrolysed.
• The monosaccharides are divided into different categories,
based on the functional group and the number of carbon
atoms
• Aldoses : When the functional group carbonyl (CHO) in
monosaccharides is an aldehyde are known as aldoses e.g.
Glyceraldehyde, glucose.
• Ketoses : When the functional group carbonyl(C=O) is a keto
group, they are referred to as ketoses e.g. dihydroxyacetone,
fructose.
• Based on the number of carbon atoms, the monosaccharides
are regarded as trioses (3C), tetroses (4C), pentoses (5C),
hexoses (6C) and heptoses (7C).

8. character of
Stereoisomerism:
• Stereoisomerism is an important
monosaccharides.
• Stereoisomers are the compounds that have
the same structural formulae but differ in their
spatial configuration.
• A carbon is said to be asymmetric when it is
attached to four different atoms or groups.
• The number of asymmetric carbon atoms (n)
determines the possible isomers of a
givencompound which is equal to 2n.
• Glucose contains 4 asymmetric carbons, and
thus has 16 isomers.

9. Optical activity of sugars
• Optical activity is a characteristic feature of compounds
with asymmetric carbon atom.
light is passed through a
it will ben rotated either to
• When a beam of polarized
solution of an optical isomer,
the right or left.
• The term dextrorotatory (+) and levorotatory (-) are used to
compounds that respectively rotate the plane of polarized
light to the right or to the left.
• An optical isomer may be designated as D(+), D(-), L(+) and L(-
)
Racemic mixture :
• lf D- and L-isomers are present in equal concentration, it is
known as racemic mixture or DL mixture.
• Racemic mixture does not exhibit any optical activity, since
the dextro- and levorotatorv activities cancel each other.

10. Epimers
• if two monosaccharides
differ from each other in
their
around
configuration
a single specific
carbon (other than
anomeric) atom, they are
referred to as epimers to
each other.
• For instance, glucose and
galactose are epimers
with regard to carbon 4.
in the
of –OH
• they differ
arrangement
group at C4.
• Glucose and mannose are
epimers regard to carbon
2 (C2-epimers).

13. Enantiomers
• Enantiomers are a special type of stereoisomers
that are mirror images of each other.
• The two members are designated as D- and L-
sugars.
• Majority of the sugars in the higher animal
(including man) are of D-type.
The term diastereomers is used to represent the
stereoisomers that are not mirror images of one
another.

14. D and L-isomers
• The D and L isomers are mirror
images of each other.
• The spatial orientation of -H and -OH
groups on the carbon atom (Cs for
glucose) that is adjacent to the
terminal primary alcohol carbon
determines whether the sugar is D-
or L-isomer.
right
and if
to L-
• lf the -OH group is on the
side, the sugar is of D-series,
on the left side, it belongs
series.
• It may be noted that the naturally
occurring monosaccharides in the
mammalian tissues are mostly of D-
configuration.
• The enzyme machinery of cells is
specific to metabolise D-series of
monosaccharides.

15. Anomers-
• The α and β cyclic forms of D-glucose are
known as anomers.
• They differ from each other in the configuration
only around C1 known as anomeric carbon
(hemiacetal carbon).
• In case of α anomer, the -OH group held by
anomeric carbon is on the opposite side of the
group -CH2OH of sugar ring.
• The reverse is true for β-anomer.
• The anomers differ in certain physical and
chemical properties.

19. Mutarotation : The α and β anomers of glucose have
different optical rotations.
• The specific optical rotation of a freshly prepared
glucose (α anomer) solution in water is +112.2°which
gradually changes and attains anequilibrium with a
constant value of +52.7°.
• in the presence of alkali, the decrease in optical rotation is
rapid.
The optical rotation of β-glucose is +18.7°. Mutarotation is
defined as the change in the specific optical rotation
representing the interconversion of α and β forms of D
glucose to an equilibrium mixture.

20. Tautomerization or
enolization
• The process of shifting a
hydrogen atom from one
carbon atom to another
to produce enediols is
known as tautomerization.
• Sugars possessing
anomeric carbon atom
undergo tautomerization
in alkaline solutions.
• When glucose is kept in
alkaline solution for
several hours, it
undergoes isomerization
to form D-fructose and D-
mannose

21. Reducing properties:
are classified as reducing or non-
• The sugars
reducing.
• The reducing property is attributed to the free
aldehyde or keto group of anomeric carbon.
Oligosaccharides
• Oligosaccharides (Greek: oligo-few) contain 2-1O
monosaccharide molecules which are liberated on
hydrolysis.
• Based on the number of monosaccharide units
present, the oligosaccharides are further
subdivided to disaccharides, trisaccharides etc.

22. Disaccharides :
• Among the oligosaccharides, disaccharides are
the most common.
• a disaccharide consists of two monosaccharide
units (similar or dissimilar) held together by a
glycosidic bond.
• They are crystalline, water-soluble and sweet
to taste.
• The disaccharides are of two types
1. Reducing disaccharides with free aldehyde or
keto group e.g. maltose, lactose.
2. Non-reducing disaccharides with no free
aldehyde or keto group e.g. sucrose, trehalose.

23. Maltose
• Maltose is composed of two α-D-glucose
units held together by α(1-4) glycosidic
bond.
• The free aldehyde group present on C1 of
second glucose.

24. Sucrose
• Sucrose (cane sugar) is the sugar of commerce,
mostly produced by sugar cane.
β-D-
• Sucrose is made up of
fructose.
• The two monosaccharides
α-D-glucose and
are held together by a
glycosidic bond (α1-β2), between C1 of α-glucose
fructose are
sucrose is a
and C2 of β-fructose.
• The reducing groups of glucose and
binvolved in glycosidic bond, hence
non-reducing sugar.

25. • Sucrose is the major carbohydrate produced
in photosynthesis

28. lnversion of sucrose
• Sucrose, as such is dextrorotatory (+66.5°).
• But, when hydrolysed, sucrose becomes
levorotatory (-28.2°).
• The process of change in optical rotation from
dextrorotatory (+) to levorotatory (-) is referred
to as inversion.
• The hydrolysed mixture of sucrose, containing
glucose and fructose, is known as invert sugar.

29. Lactose
• It is more commonly known as milk sugar since it is the
disaccharide found in milk.
• Lactose is composed of β-D- galactose and β-D-glucose
held together by β(1-4) glycosidic bond.
• The anomeric carbon of C1 glucose is free, hence
lactose exhibits reducing properties.
• Lactose of milk is the most important carbohydrate in
the nutrition of young mammals.
• It is hydrolysed
by the intestinal
enzyme lactase
to glucose and
galactose.

30. Trehalose
• Trehalose a disaccharide of α D-glucose that is like
sucrose but it is a non reducing sugar which is a
major constituent of the circulating fluid of insects,
serving as an energy-storage compound.
• Trehalose is a major constituent of the circulating
fluid (hemolymph) of insects.
• It is also found in yeasts and other fungi though it is
not common in plants. Mushrooms contain up to
10–25 % by dry weight.
• The two anomeric carbon atoms of the two α-D-
glucose moieties forms a glycosidic bond with each
other to give a molecule of trehalose.
• ASlpha-linked disaccharide formed by an α,α-1,1-
glucoside bond between two α-glucose units.

32. Lactulose
Structure:
• It is β-D-galctopyranosyl-
(1→4)-β-D-fructofuranose
Source:
• Heated milk (small amounts).
Mainly obtained synthetically.
Clinical significance:
• Not hydrolysed by intestinal enzymes, but fermented
by intestinal bacteria.
• It is used clinically in medicine as an osmotice
laxative.

33. Polysaccharides
• Polysaccharides (Greek: poly-many) are polymers of
monosaccharide units with high molecular weight (up
to a million).
• They are usually tasteless (non-sugars) and form
colloids with water.
• It consist of repeat units of monosaccharides or their
derivatives, held together by glycosidic bonds.

34. • They are primarily concerned with two
of
important functions-structural, and storage
energy.
• Polysaccharides are linear as well as branched
polymers.
• This is in contrast to structure of proteins and
nucleic acids which are only linear polymers.
• The occurrence of branches in polysaccharides is
due to the fact that glycosidic linkages can be
formed at any one of the hydroxyl groups of a
monosaccharide.

35. • The polysaccharides are of two types -
homopolysaccharides and
heteropolysaccharides.
1. Homopolysaccharides:
• which on hydrolysis yield only a single type of
monosaccharide.
• They are named based on the nature of the
monosaccharide unit.
• Thus, glucans are polymers of glucose
whereas fructosans are polymers of fructose.
2. Heteropoiysaccharides
• on hydrolysis yield a mixture of a few
monosaccharides or their derivatives.

36. Starch
• Starch is the carbohydrate reserve
dietary source
of plan which
for higher
is the most important
animals, including man.
• Starch is a homopolymer composed of D-glucose
units held by α-glycosidic bonds.
• lt is known as glucosan or glucan.
• Starch consists of two polysaccharide components-
water soluble amylose (15-20%) and a water
insoluble amylopectin (80-85%)
• Chemically, amylose is a long unbranched chain
units held by α(1 -4)
with 200-1,000 D-glucose
glycosidic linkages.

37. • Amylopectin, on the other hand, is a branched
chain with α(1 -6) glycosidic bonds
branching points and α (1-4)
at the
linkages
everywhere else.
• Amylopectin molecule containing a few
thousand glucose units looks like a branched
tree (20-30 glucose units per branch).
• Starches are hydrolysed by amylase (pancreatic
or salivary) to liberate dextrins, and finally
maltose and glucose units.
• Amylase acts specifically on α (1-4) glycosidic
bonds.

40. Hydrolysis of starch:
• It yields succession of polysaccharides of gradually
diminishing molecular size.

41. is the carbohydrate reserve in
hence often referred to as animal
Glycogen
• Glycogen
animals,
starch.
• It is present in high concentration in liver,
followed by muscle, brain etc.
• Glycogen is also found in plants that do not
possess chlorophyll (e.g. yeast, fungi).
• The structure of glycogen is similar to that of
amylopectin with more number of branches.
• Glucose is the repeating unit in glycogen joined
together by α(1-4) glycosidic bonds, and α(1 -6)
glycosidic bonds at branching points

43. Cellulose
• Cellulose occurs exclusively in plants and it is the
most abundant organic substance in plant kingdom.
• lt is a predominant constituent of plant cell wall.
• Cellulose is totally absent in animal body.
• Cellulose is composed of β-D-glucose units linked by
β(1-4) glycosidic bonds.
• Cellulose cannot be digestedby mammals including
man-due to lack of the enzyme that cleaves β-
glycosidic bonds (a amylase breaks α bonds only).
• Certain ruminants and herbivorous animals contain
microorganisms in the gut which produce enzymes
that can cleave β-glycosidic bonds.
• Cellulose, though not digested, has great importance
in human nutrition.

44. • lt is a major constituent of fiber, the non-digestable
carbohydrate.
• The functions of dietary fiber include decreasing the
absorption of glucose and cholesterol from the
intestine, besides increasing the bulk of feces.
Chitin
•Chitin is composed of N-acetyl D-glucosamine units held
together by β (1-4) glycosidic bonds.
•lt is a structural polysaccharide found in the exoskeleton of
some invertebrates e.g. insects, crustacean

45. Heteropolysaccharide

49. Glycoproteins:
• Several proteins covalently bound
are
which are
to
referred to as
carbohydrates
glycoproteins.
• The carbohydrate content of glycoprotein varies
from 1% to 90% by weight, Sometimes the term
mucoprotein is used for glycoprotein with
carbohydrate concentration more than 4%.
• Glycoproteins are very widely distributed in the cells
and perform variety of functions.
• These include their role as enzymes,hormones,
transport proteins, structural proteins and receptors.
• The carbohydrates found in glycoproteins include
acetylgalactosamine, xylose,L-fucose and
mannose, galactose, N-acetyl-glucosamine, N-
N-
acetylneuraminic acid (NANA).