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Lecture 09-Carbohydrates (FM)
Lecture 09-Carbohydrates (FM)
Lecture 09-Carbohydrates (FM)
Maltose
(Glu + Glu)
Sucrose
(Glu + Fruc)
Glucose (Glu) Fructose (Fruc)
Carbohydrates
C + H2O
Therefore, the general formula of carbohydrates is Cn(H2O)n
Hence, Cn(H2O)n is equal to 1:2:1 ratio
= hydrated carbon
(Carbon attached to -H and -OH)
Glucose Fructose Ribose Erythrose
(Tetrose or 4-carbon
carbohydrates)
Hydrolysis = Chemical
breakdown of a compound due to
reaction with water
2.0 Source of carbohydrates
β-1,4-glycosidic bonds
Hydrogen bonds
What is the implication of
β-1,4-glycosidic and
Hydrogen bonds??
iii) What is glycosidic bond?
→ Also known as “glycosidic linkage”
→ A covalent bond connecting a sugar monomer to another sugar via
condensation
Hydrolysis = any chemical reaction in which a molecule of water breaks one or more chemical
bonds
Condensation = two molecules are combined to form a single molecule, releasing water
Chair confirmation
Different
representations
of β-glucose in
cellulose
1
Howarth structure
iv) Where cellulose can be found?
→ Microfibril is stronger
than genuine leather!
v) The importance of cellulose for humans
❖ Source of fiber
-Humans cannot digest cellulose
-But cellulose is important to keep the digestive tract working
smoothly
❖ Industrial uses
-Paper, textile, etc.
Can herbivores digest cellulose?
Amylose
100-10K glucose monomers, linked by
1 α1-4 glycosidic linkage
Amylopectin
2 mil glucose monomers, linked by α1-4
glycosidic linkage (linear) and α1-6
2 glycosidic linkage (branch)
The main component of starch
Largest molecules in nature
iv) Amylose vs Amylopectin
Amylose Aspects Amylopectin
α-glucose Subunit α-glucose
α1-4 glycosidic linkage Bonding α1-4 glycosidic and α1-
6 glycosidic linkages
Parenchyma cells
Apple Potato
vi) Hydrolysis of starch in plants Maltose
❖Used as energy for germinating
seeds
❖Maltose further breakdown into
glucose
Maltose = Glucose + Glucose
Maltose = Disaccharides
Maltose = Sweet, dissolved in water
Glucose
❖Joined together to make the cell
wall
❖Combined with nutrients to make
protein
❖Converted into lipids (fat and oil)
for the seeds
Glucose = Monosaccharides
Glucose = Sweet, dissolved in water
Maltose and Glucose are Sugar carbohydrates!
Therefore,
❖ Brewing
-As the raw material (maltose) of fermentable sugar (beer).
Thus, maltose also known as “beer sugar”
(a) Cellulose vs Starch
Glucose Maltose
Ribose Sucrose
Glucose Ribose
→ A monosaccharide → A monosaccharide (single
(single sugar) sugar)
→ Important source of → Constituent of active
energy (respiration) molecules such as ATP
→ Building monomer and NAD
of starch and
cellulose
Adenosine
Nicotinamide adenine triphosphate (ATP)
Starch dinucleotide
Cellulose (NAD)
Maltose Sucrose
→ A Disaccharide (double sugar) → A Disaccharide (double sugar)
→ Act as an electron donor in a → Also known as table sugar
chemical reaction (cane sugar)
→ Important for seed → Used to transport carbon
germination within plants
2.2 Animal
2.2.1 Lactose (Milk sugar)
→ The only simple sugar (disaccharides) of animal-origin
→ Can be found in milk (hence, known as milk sugar)
→ Formed from the condensation of glucose and galactose Glucose
Monosaccharides Disaccharides
Polysaccharides
(Glucose, (Sucrose, maltose,
(Cellulose, starch)
galactose fructose) lactose)
4.2 The product of hydrolysis: : the most complete classification?
→ Hydrolysis = any chemical reaction in which a molecule of water breaks one
or more chemical bonds
Stachyose (Tetrasaccharides)
→ 2 galactose + glucose + fructose
→ Naturally occur mostly in beans
→ Storage and transport of sugar in woody plants and legumes
→ Partially digestible by humans
Heteropolysaccharides → Hetero = different, Poly = Many, Saccharides = sugars
Hemicellulose
→ A heteropolysaccharide.
→ Second most abundant
carbohydrates, mostly found in
woody plants.
→ Shorter than cellulose (100-200
units)
Carbohydrates
(Based on the product
of hydrolysis)
Monosaccharides
Oligosaccharides
Glucose, galactose, Polysaccharides
(<5 monomers)
fructose
Disaccharides
Homopolysaccharides
Lactose, sucrose,
Cellulose, starch
maltose
Trisaccharides Heteropolysaccharides
Raffinose Hemicellulose
Tetrasaccharides
Stachyose
4.3 Reducing property
→ Reducing property = compound that reduces another compound, and itself
undergoes oxidation.
Aldehyde Ketone
→ Aldehydes are stronger reducing agents than ketone due to the presence of
hydrogen atoms (aldehydes are very easy to oxidize)
It is important to note that:-
→ “Glucose” refers to its open form
→ “Glucopyranose” refers to glucose in cyclic form
→ Anomeric carbon forms the hemiacetal group
→ In its ring forms, glucose (also known as glucopyranose) is not reducing sugar at ROOM TEMPERATURE (No free anomeric
carbon) → at higher temperatures, the cyclic form will open
Pyranose = monosaccharide in cyclic hemiacetal form, containing a pyran ring
Glucose
Free -CHO acts
Lactose as a reducing
end. Hence,
lactose is a
reducing
disaccharides
Possibility to form
free -CHO does not
exist in sucrose.
Thus, sucrose is a
non-reducing
disaccharides Maltose?
Sucrose
Therefore, not all disaccharides are reducing sugar
Tautomerization = process by which protons are transferred from one site to another
An important process to convert Ketose into the readily oxidized form
Carbohydrates
Overall,
(Based on reducing
→Free anomeric carbon
property) (with aldehyde/ketone
group)
→All monosaccharides are
reducing sugar (both
Reducing sugar Non-reducing sugar
with aldehyde and
(Free anomeric (No free anomeric
carbon) carbon) ketone group)
→Only some disaccharides
are reducing sugars
Polysaccharides
→Most oligosaccharides
Monosaccharides Disaccharides Oligosaccharides
(Sucrose, (Cellulose,
and polysaccharides are
(all (Maltose,
monosaccharides) lactose) raffinose) starch) non-reducing sugar.
4.4/4.5 Based on functional group and number of carbon
→ These classifications only apply to monosaccharides.
→ Functional groups in monosaccharides are aldehyde and ketone
on 5 criteria Sugar
Sweet, soluble
Non-sugar
Non-sweet, insoluble
Glucose = Dextrose!
It is important to note that:-
→ “Glucose” refers to its open form
→ “Glucopyranose” refers to glucose in cyclic form
→ Anomeric carbon forms the hemiacetal group
→ In its ring forms, glucose (also known as glucopyranose) is not reducing sugar at ROOM TEMPERATURE (No free anomeric
carbon) → at higher temperatures, the cyclic form will open
• Dextrose = D-glucose
• Glucose = open chain
• Glucopyranose = cyclic form
• α-glucose
• Β-glucose
• α-D-glucopyranose
• β-D-glucopyranose
4.2 Howarth structures
Definition Application Example
→Representing the → Showing the structure of
structural formula of in monosaccharides
cyclic form → Improving cyclic Fisher’s
projection
1
1 1 1 6
2 2 2 2
5
3 3 3 4
1
4 4 4 6 3
6 6 5 3 2
5 5 5
4
6
Ketose Aldose
Aldose (aldehyde)
6.0 Importance of carbohydrates
6.1 Energy production
→ The main source of energy, providing 4 kcal/g
→cellular respiration involved three processes:
i) Glycolysis
ii) Krebs cycle (or tricarboxylic acid (TCA))
iii) Electron transport chain (ETC)
6.2 Energy storage
→In the presence of abundant energy (from processes in 6.1), the excess glucose
is stored as glycogen in the liver.
→Glucose is converted into glycogen through a process known as glycogenesis
→Glycogenolysis = breakdown of glycogen to glucose
6.3 Building macromolecules
Nicotinamide adenine
dinucleotide
(NAD)
Adenosine
triphosphate (ATP)
7.0 Other source of glucose
→When glucose is not enough to meet the body’s needs, glucose is synthesized
from non-carbohydrates (amino acids).
→ The process is known as Gluconeogenesis, which requires the destruction of
muscle.
→The presence of storage carbohydrates (glycogen), spares the breakdown of
muscle.
Overall remarks
→Carbohydrates are mainly produced by plants (cellulose the
most abundant)