Lecture 09-Carbohydrates (FM)

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Macromolecules Central Dogma

→Nucleic acid (MKS)


→Protein (MKS)
→Lipid (MKS)
→Carbohydrates
→ Introduction
→ Anabolism (photosynthesis)
→ Metabolism (glycolysis, TCA, PPP, ETC, gluconeogenesis)
Carbohydrates
FM
Lecture outlines
1.0 What are carbohydrates?
1.1 Definition 1-Based on taste
1.2 Definition 2-Based on the hydration of carbon
1.3 Definition 3-Based on the overall structure
2.0 Source of carbohydrates
2.1 Plants
2.1.1 Cellulose
2.1.2 Starch
(a) Cellulose vs Starch
2.1.3 Simple sugars from plants – Glucose, sucrose, maltose, and ribose
2.2 Animal
2.2.1 Lactose
3.0 Classification and nomenclature of carbohydrates
3.1 Based on taste and solubility in water
3.2 Based on the product of hydrolysis: the most complete classification?
3.3 Based on reducing power
3.4 Based on the functional group
3.5 Number of carbon
4.0 Ways to draw carbohydrates
4.1 Fischer projection
4.1.1 D-, L-, α-, and β-forms of carbohydrates
4.2 Howarth Structure
4.2.1 Converting Fischer projection to Howarth structure
4.3 Chair confirmation
4.4 Other ways to draw the chemical structure
5.0 Tests to identify the presence of different types of carbohydrates
5.1 Benedict test
5.2 Iodine test
5.3 Fehling test
5.4 Molisch test
5.5 Tollens test
6.0 The importance of carbohydrates
6.1 Energy production
6.2 Energy storage
6.3 Building macromolecules
7.0 Other source of glucose
1.0 What are carbohydrates?

→Carbohydrates are biomolecules consisting of carbon, hydrogen, and oxygen

Biomolecules = organic molecules produced by living organisms (lipid, protein,


nucleic acid, and carbohydrates)
→ It is 1 of 3 classes of food:-
a) Carbohydrates (energy)
b) Protein (body-building)
c) Vitamins/minerals (protective)
1.1 Definition 1: Based on taste and solubility in water
Derived from the Greek word “Sakcharon” → “Saccharides” or “sugar”
Definition of sugar
→Water soluble (due to the presence of hydroxyl group (-OH))→
→ Sweet-tasting carbohydrates (why?) Hydrogen bond

→ All Mono and Di- saccharides are sugar!

Maltose
(Glu + Glu)

Sucrose
(Glu + Fruc)
Glucose (Glu) Fructose (Fruc)

Monosaccharides = Mono (single) + Saccharides (sugar) Disaccharides = Di (double) + Saccharides (sugar)


Why sugars are sweet?
Sugar contains -OH groups at specific orientation which interacts with taste
receptors in the tongue Only small carbohydrates
(mono-/disaccharides) with
specific orientation to
interact with the sweet
receptor; especially the
hemiacetal group

Bioinformatics (molecular docking) – 3rd year subject?


The problem definition-1: All sugars are Hemiacetal group = carbon connected to
carbohydrates, but not all carbohydrates are two oxygen (one is alcohol/hydroxyl
sugar (sweet) (OH) + ether (O, OR)
1.2 Definition 2: Based on the hydration of carbon
“Carbohydrates” are literally hydrates of carbon (1)

Hydrates of carbon = at least 1 carbon molecule bearing Hydrogen (H) and


hydroxyl (OH)

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)

(Hexose or 6-carbon (Pentose or 5-carbon Glyceraldehyde


carbohydrate) carbohydrates) (Trioses or 3-carbon
carbohydrates)
1.3 Definition 3: Based on the structure overall structure
Carbohydrates are (1) polyhydroxy aldehydes or ketone, or (2) substances that
yield these compounds on hydrolysis (hydrolysis = water molecules break the
chemical bond(s))
Polyhydroxy = containing >1 hydroxyl (OH) AND
Aldehydes = Chemicals containing R-CH=O (aldose sugars) OR
Ketones = Chemicals containing ‘R-C(=O)-R (ketose sugars) OR
Aldehyde
Ketone

>1 hydroxyl group


>1 hydroxyl group
= Aldehyde group = Ketone group Containing > 1 -OH
(Aldose sugar) (Ketose sugar)

6-carbon sugar Glucose ✓ Aldehyde group


Aldehyde
(Hexose) ✓ >1 –OH
Hence, glucose is a
Because it is an
sugar/
Aldose sugar, Total = 5 -OH
carbohydrates
therefore, a
Aldohexose
sugar

Overall conclusion, Glucose is an aldohexose


sugar/carbohydrates
= Aldehyde group = Ketone group Containing > 1 -OH
(Aldose sugar) (Ketose sugar)

6-carbon sugar Fructose ✓ Ketone group


(Hexose) Ketone ✓ >1 –OH
Hence, fructose is
Because it is a a sugar/
Ketose sugar, Total = 5 -OH
carbohydrates
therefore, a
Ketohexose
sugar

Overall conclusion, Fructose is a ketohexose


sugar/carbohydrates
Definition 3: Based on the
structure overall structure
Carbohydrates are polyhydroxy
aldehydes or ketone, or
substances that yield these
compounds on hydrolysis
(hydrolysis = water molecules
break the chemical bond(s))

Hydrolysis = Chemical
breakdown of a compound due to
reaction with water
2.0 Source of carbohydrates

→Carbohydrates are the product of photosynthesis by plants (an anabolic


process).

Anabolic/anabolism = The building of complex biomolecules from simple


subunits

→60% - 90% of plant dry weight is carbohydrates (mainly cellulose)


→Therefore, the main source of carbohydrates is from plants.
→Lactose is the ONLY simple carbohydrate produced by animals
2.1 Plants
2.1.1 Cellulose
→ Produced by ALL plants (all parts)
→ Made up most of the plant cell wall (30%)
→ Therefore, cellulose is the most abundant carbohydrates

i) The importance of cellulose in plants


❖ Structural
→ A Structural Polysaccharide (Poly = Many, Saccharides = sugar)
→ Maintaining the shape of plant cells and rigidity of the cell wall (withstand
turgor pressure of fluids). Hence, helps plants remain stiff and strong
❖ Biological function
→ Connecting cells to form tissue
→ Signaling cells to grow and divide
ii) The structure of cellulose
→ Cellulose consists of a single type of monomer (β-glucose)
→ Therefore, cellulose is Homopolysaccharide!
(Homo = Same, Poly = Many, Saccharides = Sugar)

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?

What is the implication of


β-1,4-glycosidic and
Hydrogen bonds?

→ Increase the strength of


cellulose = microfibril

→ 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?

→ Although plants are the diets of herbivores, like humans, they


cannot digest cellulose.

→ Herbivores depend on symbiotic bacteria (Ruminococcus) in


their guts that produce cellulase, an enzyme that can
breakdown cellulose into its monomers (β-glucose)
→ Endoglucanase, Exoglucanase, and β-
Glucosidase are cellulase (enzyme)
produced by Ruminococcus in the rumen
(gut) of herbivores.

→ Cellulase is categorized as glycosyl


hydrolase, which catalyzes the hydrolysis
of glycosidic bonds.

Definition 3: Based on the structure overall


structure
Carbohydrates are polyhydroxy aldehydes or
ketone, or substances that yield these
compounds on hydrolysis (hydrolysis = water
molecules break the chemical bond(s))
Therefore,

Although cellulose does not dissolve in water and is not sweet


hence, it is not a sugar (does not fit the first definition of
carbohydrates)

However, Its hydrolysis produces glucose (a monosaccharide)


(dissolved in water and tastes sweet!) (fits the third definition
of carbohydrates, hence cellulose a carbohydrate!))

Thus, cellulose is categorized as a “non-sugar carbohydrate”


2.1.2 Starch

→ Also known as amylum


→ Source: corn, potato, peas, rice, etc. (in grains, tuber, seeds)
→ Tasteless, odorless, white in color, and generally insoluble in water
→ The most important source of carbohydrates for humans

i) The importance of starch in plants


a) Energy storage
→ A storage polysaccharide (Poly = Many, Saccharides = sugar)
→ To store energy, in OSMOTICALLY INERT form

Osmotically inert = No effect on water balance


ii) The structure of starch

→ Starch consists of a single type of monomer (α-glucose).

Therefore, starch is Homopolysaccharide!

(Homo = Same, Poly = Many, Saccharides = Sugar)

→ Exist as amylose (linear (coiled like spring); 20-30%) or amylopectin (branched;


70-80%)
iii) 2-components of starch

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

Linear (coiled) Structure Branch


~20-25% Constituent ~75-80%
Soluble in water Solubility Insoluble in water
It can be hydrolyzed Activity against It cannot be hydrolyzed
completely β-Amylase completely
v) Where starch can be found?

Parenchyma cells

Potato tuber parenchyma tissue (cellular tissue)


Starch mainly exists as amylopectin (water
insoluble), semi-crystalline granule in plant
organelles (amyloplast, chloroplast)

Starch does not dissolve in water,


therefore NOT a sugar!
What stain can be used to stain/visualize starch?

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,

Although starch (amylopectin) is not dissolved in water and


is not sweet (amylose and amylopectin), hence, not a sugar
(does not fit the first definition of carbohydrates)

However, Its hydrolysis produces maltose (a disaccharide)


and glucose (a monosaccharide) (both dissolved in water and
taste sweet!) (fit the third definition of carbohydrates)

Thus, starch is categorized as a “non-sugar carbohydrate”


vii) The importance of starch for humans
❖ Source of energy

❖ Food stabilizers/thickening (food industry)


-Baked products, Confectionery, Pasta, Pudding

❖ Brewing
-As the raw material (maltose) of fermentable sugar (beer).
Thus, maltose also known as “beer sugar”
(a) Cellulose vs Starch

Cellulose Aspects Amylose Amylopectin


Structural Type Storage Storage
β-glucose Monomer α-glucose α-glucose
β-1,4-glycosidic and Linkage α-1,4-glycosidic α1-4 glycosidic and α1-6
hydrogen bonds glycosidic linkages
Linear Structure Linear Branch
Difficult Breakage Easy Medium
Cellulase Hydrolyzing enzyme Amylase Amylase
Structural Function Storage Storage
2.1.3 Simple sugar from plants
→ Simple sugar = containing 1 or 2 sugar monomers
→ Therefore, Monosaccharides and Disaccharides are simple sugar
→ The most abundant/common simple sugar in plants are glucose, ribose,
maltose, and sucrose

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

i) The importance of lactose in humans Galactose


→ Influence gut microbiota
→ Supply galactose for glycogen synthesis in human
→ Enhance adsorption/retention of minerals (calcium, magnesium, and
manganese)
Lactose intolerant
Definition = Individual unable to digest lactose
Effect = Digestive issue, diarrhea
Why?
→Some individuals are unable to produce “Lactase”
to degrade/hydrolyze lactose.
→Different that cellulase, lactase is not produced by
gut microbiota
→Instead, it is produced by cells in the human's
small intestine
3.0 Classification of carbohydrates
Carbohydrates classification is based on Five aspects:-

3.1 Taste and Solubility in water (Sugar and non-sugar)


3.2 The product of hydrolysis (Mono-, oligo-, and polysaccharides)
3.3 Reducing property (reducing and non-reducing sugar)
3.4 Functional group (Aldehyde, ketone; aldose and ketose sugar
respectively)
3.5 The number of carbons (3-, 4-, 5-, 6-, and 7-C sugar)
4.1 Taste and solubility in water
→ So far, we know that carbohydrates are also known as “Sugar”
→ Sugar can be characterized as sweet and water-soluble chemicals
→ However, not all carbohydrates are sweet and water-soluble
→ Therefore, based on taste and solubility, carbohydrates can be divided into
sugar and non-sugar Carbohydrates
(Based on taste and solubility in water)

Sugar (Saccharides) Non-sugar


(Sweet, water-soluble) (not sweet, insoluble)

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

❖ Carbohydrates that do not hydrolyze further into smaller units (glucose,


galactose, fructose) = Monosaccharides!

❖ Carbohydrates yield 2-10 units of monosaccharides upon hydrolysis.


Therefore, oligosaccharides can be further divided into Disaccharides (2 units;
sucrose, maltose, lactose), Trisaccharides (3 units; raffinose), and
Tetrasaccharides (4 units; stachyose) = Oligosaccharide!

❖ Carbohydrates that yield many monosaccharides upon complete hydrolysis.


Based on the subunits, polysaccharides can be further divided into
homopolysaccharides (cellulose, starch) and heteropolysaccharides
(hemicellulose) = Polysaccharides
Raffinose (Trisaccharides)
→ A sucrose derivatives (Sucrose + Galactose)
→ Serve as transport sugar, energy storage, and desiccation
(water loss) protectant in seeds
→ Can be digested by humans (by α-galactosidase-
producing bacteria in the digestive tract)

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.

Oxidation = the carbonyl group of sugar is oxidized to a carboxyl group

Aldehyde Ketone

→ Reducing sugar is a sugar whose open-chain form HAS


a) Free anomeric carbon (with aldehyde/ketone group) OR Anomeric carbon
b) Hemiacetal group (OH and O) (Reducing end of sugar)
Therefore, ALL monosaccharides are reducing sugar!

→ 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

Pyran ring = 6-membered heterocyclic, containing FIVE carbon + ONE oxygen


Therefore,

The cyclic form of glucose is also known as


C5 O1 Glucopyranose
C4 C1 Hence fructose also known as fructofuranose in its
cyclic form
C3 C2

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

→ Meanwhile, no of carbon are; 3-carbon (triose), 4-carbon (tetrose), 5-carbon (pentose), 6-


carbon (hexose), and 7-C (heptose)
→ “Ose” a suffix used to name sugar, derived from -ōsus; the Latin word for sucrosus (sweet)
= Aldehyde group = Ketone group Containing > 1 -OH
(Aldose sugar) (Ketose sugar)

6-carbon sugar Glucose ✓ Aldehyde group


Aldehyde
(Hexose) ✓ >1 –OH
Hence, glucose is a
Because it is an
sugar/
Aldose sugar, Total = 5 -OH
carbohydrates
therefore, a
Aldohexose
sugar

Overall conclusion, Glucose is an aldohexose


sugar/carbohydrates
= Aldehyde group = Ketone group Containing > 1 -OH
(Aldose sugar) (Ketose sugar)

6-carbon sugar Fructose ✓ Ketone group


(Hexose) Ketone ✓ >1 –OH
Hence, fructose is
Because it is a a sugar/
Ketose sugar, Total = 5 -OH
carbohydrates
therefore, a
Ketohexose
sugar

Overall conclusion, Fructose is a ketohexose


sugar/carbohydrates
Based on functional group and number of carbon,
monosaccharides can be classified as follow
No. of carbon atoms Aldoses Ketoses
3 (Triose) Aldotriose Ketotriose
e.g: Glyceraldehyde e.g: Dihydroxy acetone
4 (Tetrose) Aldotetrose Ketotetrose
e.g: Erythrose e.g: Erythrulose
5 (Pentose) Aldopentose Ketopentose
e.g: Ribose, xylose, arabinose e.g: Ribulose, xylulose
6 (Hexose) Aldohexose Ketohexose
e.g: Glucose, galactose, mannose e.g: Fructose
7 (Heptose) Aldoheptose Ketoheptose
e.g: Glucoheptose, galactoheptose e.g: Heptulose
Overall
carbohydrates Classification of

classification, based Carbohydrates

on 5 criteria Sugar
Sweet, soluble
Non-sugar
Non-sweet, insoluble

Monosaccharides Oligosaccharides Polysaccharides


(all reducing sugar) (Some are reducing sugar) (Non-reducing sugar)

Trisaccharides Tetrasaccharides Homopolysaccharides


Aldose Disaccharides
Raffinose Stachyose Cellulose, starch
Glucose, galactose
(6-C; Aldohexose)
Reducing sugar Heteropolysaccharides
Lactose, maltose Hemicellulose
Ketose
Fructose (6-C; Non-reducing sugar
Ketohexose)
Sucrose
4.0 Ways to draw carbohydrates?
4.1 Fisher’s projection
Definition Application Example
→A two-dimensional →Mainly used to represent
representation (like a the structure of
paper) of three- carbohydrates
dimensional molecules →To show chirality (non-
superimposable mirror
image)
→Distinguish enantiomers
4.1.1 D-, L-, α-, and β-forms of carbohydrates
→ In nature, D-glucose is more
abundant. L-glucose is less
* *
* *
biologically active and cannot be
* * used as a source of energy.
* * → D-glucose can further exist as two
isomers in water (mutarotation):-
a) α-D-glucose (or α-D-glucopyranose)
Chiral carbon (*) b) β-D-glucose (or β-D-glucopyranose)
→ Carbon attaches to 4 different
atoms or groups
→Optically active (can rotate light)
→The L-glucose configuration
indicated by the mirror image of
D-glucose
D = Dextrorotatory (turning clock-wise or rotating to the right)
L = Levorotatory (turning anti-clock-wise or rotating to the left)

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

Fisher projection Cyclic Fisher projection Howarth structure


4.2.1 Converting Fischer projection to Howarth structure

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

The golden rule:


1) Any group on the right in a Fischer projection appears below the plane of the ring in a
Haworth projection.
2) Any group on the left in a Fischer projection appears above the plane in a Haworth projection.
3.3 Chair confirmation
Definition Application Example
→Draw the structure of →To represent cycloalkanes →For cyclohexane (6-
cyclic compounds with no in the most stable form. membered ring), atoms 2,
torsional and ring strain 3, 5, and 6 lie in the same
(more stable) plane
→Atom 1 and 4 points
above and below the
plane respectively
Torsional strain can be defined as an increase in the potential energy of a molecule due to
repulsion between electrons in bonds that do not share an atom (adjacent atoms).

Greater repulsion Less repulsion


between electrons between electrons
4.4 Other ways to draw chemical structures

Perspective drawing Space-filling model Ball and stick drawing


5.0 Tests to identify the presence of different types of
carbohydrates
5.1 Benedict test – Reducing sugar
5.2 Iodine test – Starch
5.3 Fehling test – Reducing sugar (glucose, fructose, lactose)
5.4 Molisch test – General carbohydrates
5.5 Tollens test – to distinguished aldehyde and ketones
5.1 Benedict test
→Used to detect simple reducing sugar (mono- and disaccharides), bearing
aldehyde of ketone groups.
→Positive result = Red-brick precipitation
→Principle: 2+ +
Cu ions are reduced to Cu ions

A qualitative or quantitative test?


5.2 Iodine test
→Used to detect the presence of starch
→ Positive result = Blue black color
→Principle: Iodine interacts with amylose to form a black colored complex
5.3 Fehling test
→Used to detect reducing sugar, bearing aldehyde
→Positive results = Red-brick precipitation (aldehyde)
Principle:

Ketose Aldose

Because of their structure, ketones do not react with Fehling’s.


The H atom is not directly linked to the carbonyl group in a
ketone. Thus, ketones are not readily oxidized whereas
aldehydes are.
5.4 Molisch test
→Used to detect the presence of ANY carbohydrates
→Positive results = Purple/violet ring (between acid and sample)
→Principle: Carbohydrates react with acid and get dehydrated + naphthol and get
condensed, forming purple-colored product
5.5 Tollens test
→Also known as the “silver mirror test”
→Used to distinguish aldehyde and ketone (Aldoses are readily oxidized)
→Positive results = Metallic silver indicates the presence of aldehyde (aldose
sugar)
→Principle:

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)

→The definition of carbohydrates needs to consider different


aspects (Taste, solubility in water (Poly -OH), structural
features-Aldehyde, ketone) → the “fingerprint” of
carbohydrates”

→The most complete classification of carbohydrates is based on


the product of hydrolysis (Mono-, Oligo-, and Polysaccharides)
→Fisher and Howarth’s projections are the most common way
to represent carbohydrates, but Chain confirmation represents
the low-energy representation (hence accurate)

→D-form is the most abundant form of carbohydrates in


nature, further divided into alpha- and beta-forms

→Different tests can be applied to predict/identify the class of


carbohydrates; highly selective and wide sensitivity
→Carbohydrates are the source/storage of energy and
macromolecules building materials in both plants and animals

→Carbohydrates also serve as supporting/structural material in


plants
Next,
We will look at carbohydrate anabolism and catabolism
involving these cell processes:-
1) Photosynthesis
2) Calvin cycle
3) Glycolysis
4) Krebs Cycle
5) Electron transport chain
6) Glycogenesis, Glycogenolysis, and Gluconeogenesis

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