UNIT-15

BIOMOLECULES

 Living systems are composed of some organic chemical.

1. Carbohydrates
2. Fats
3. Lipids
4. Proteins
5. Nucleic Acids

Carbohydrates
Polyhydroxy aldehyde/Ketone is called Carbohydrate and the compounds which produce such unit
on hydrolysis are also Carbohydrates.

E.g.(1) Glucose [𝑪𝟔 𝑯𝟏𝟐𝑶𝟔 ]

𝐶𝐻𝑂
| → 5(−𝑂𝐻) Group
(𝐶𝐻 − 𝑂𝐻)4 → 1(−𝐶𝐻𝑂) Group
| → Polyhydroxy Aldehyde
𝐶𝐻2 − 𝑂𝐻

E.g.(2) Fructose [𝑪𝟔 𝑯𝟏𝟐𝑶𝟔 ]

𝐶𝐻2 − 𝑂𝐻
| → 5(−𝑂𝐻) Group
𝐶𝑂 → 1(−𝐶𝑂−) Group
| → Polyhydroxy Ketone
(𝐶𝐻 − 𝑂𝐻)3
|
𝐶𝐻2 − 𝑂𝐻

E.g.(3) Sucrose [𝑪𝟏𝟐 𝑯𝟐𝟐𝑶𝟏𝟏 ]

→ 10(−𝑂𝐻) Group
→ 𝑁𝑂(−𝐶𝐻𝑂) Group
→ 𝑁𝑂(−𝐶𝑂−) Group

𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
Sucrose Glucose Fructose

NOTE
Carbohydrates which are sweet in taste are called Sugar.

 The most common sugar used in home is Sucrose. Whereas sugar present in milk is Lactose
[𝐶12 𝐻22 𝑂11 ]

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 Carbohydrates

Sugar Non-Sugar
(On-hydrolysis 10-100 Units of Monosaccharide
Poly Saccharides
Starch (𝐶6 𝐻10 𝑂5 )𝑛
Cellulose

Monosaccharide Oligosaccharide
(Can’t hydrolysis) (On-hydrolysis 2-10 Units of Monosaccharide)

Aldoses Ketoses Disaccharides Tri-saccharides Tetra-saccharides

E.g. E.g. E.g. E.g. E.g.
Glucose Fructose Sucrose Raffinose Stachyrose
(𝐶6 𝐻12 𝑂6 ) (𝐶6 𝐻12 𝑂6 ) (𝐶12 𝐻22 𝑂11 ) [𝐶18 𝐻32 𝑂16 ] [𝐶24 𝐻42 𝑂21 ]

Glucose + Fructose
+ Galactose
(𝐶6 𝐻12 𝑂6 )

Non-Reducing and Reducing Sugars

 The carbohydrate containing free aldehyde (−𝐶𝐻𝑂) or ketonic (−𝐶𝑂−) group can reduce
Fehling’s solution and tollen’s reagents are known as reducing sugar.
 The carbohydrates in which the reducing parts are not free can’t reduce Fehling solution and
Tollen’s reagent are known as Non-Reducing Sugar.
 In Sucrose, reducing part of Glucose (−𝐶𝐻𝑂) is bonded with reducing part of fructose
(−𝐶𝑂−). So, this disaccharide is non-reducing sugar.
 All disaccharidy except-sucrose are reducing in nature.
 All polysaccharide like Starch, Cellulose are non-reducing sugar.

Glucose (𝑪𝟔 𝑯𝟏𝟐 𝑶𝟔 )

Preparation Method
1. From Sucrose
𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂16 + 𝐶6 𝐻12 𝑂16
Glucose Fructose

2. From Starch [Commercial Method]

𝐻+
(𝐶6 𝐻10 𝑂5 )𝑛 + 𝑛𝐻2 𝑂 𝑛 𝐶6 𝐻12 𝑂6
393 𝐾 2 − 3𝑎𝑡𝑚

ASHISH TYAGI Page 2

Structure of Glucose
Its structure has been determined on the basis of following observation.

1. Molecular Formula
On the basis of elemental analysis and molecular weight determination. Its formula is found
to be 𝐶6 𝐻12 𝑂6

2. Presence of Straight Chain of 𝑪 −atom

On prolonged heating with 𝐻𝐼, it form 𝑛 − ℎ𝑒𝑥𝑎𝑛𝑒 suggesting that all the 6 𝐶 −atom are linked
in a straight chain.
𝐶𝐻𝑂
|
𝐻𝐼, ∆
(𝐶𝐻 − 𝑂𝐻)4 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
[𝐴𝑙𝑙 𝑂 𝑜𝑢𝑡]
|
𝐶𝐻2 − 𝑂𝐻

3. Presence of Carbonyl [− CHO or –CO−] Group

Glucose reacts with 𝐻2 𝑁 − 𝑂𝐻 to form an oxime and reacts with 𝐻𝐶𝑁 to form cyanohydrin.
These reaction confirm the presence of a carbonyl group in glucose.
𝐶𝐻 = 𝑂 𝐻𝐶 = 𝑁 − 𝑂𝐻
| |
𝐻2 𝑁−𝑂𝐻
(𝐶𝐻 − 𝑂𝐻)4 (𝐶𝐻 − 𝑂𝐻)4
𝐻𝑦𝑑𝑟𝑜𝑥𝑦𝑙 𝐴𝑚𝑖𝑛𝑒
| |
𝐶𝐻2 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻
Glucose Oxime

OH
𝐻−𝐶 =𝑂 HC
| 𝐻 | CN
(𝐶𝐻 − 𝑂𝐻)4 + | (𝐶𝐻𝑂𝐻)4
| 𝐶𝑁 |
𝐶𝐻2 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻
Glucose Cyanohydrin

4. Presence of Aldehyde Group [−𝑪𝑯𝑶]

On reaction with oxidising agent like 𝐵𝑟2 water, glucose gets oxidised into Gluconic Acid. This
indicate that carbonyl group is present as an (−𝐶𝐻𝑂) group.

𝐻−𝐶 =𝑂 𝐶𝑂𝑂𝐻
| |
𝐵𝑟2
(𝐶𝐻 − 𝑂𝐻)4 (𝐶𝐻 − 𝑂𝐻)4
𝑊𝑎𝑡𝑒𝑟
| |
𝐶𝐻2 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻
Gluconic Acid
5. Presence of 𝟓(−𝑶𝑯) Group
Acetylation of Glucose with acetic anhydride gives glucose penta-acetate which confirms
the presence of 5(−𝑂𝐻) group. Since it exist as a stable compound so 5(−𝑂𝐻) group should
be attached to different 𝐶 −atom.

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 𝐶𝐻𝑂 𝐶𝐻𝑂
| 𝐶𝐻3 − 𝐶𝑂 |
(𝐶𝐻 − 𝑂𝐻)4 + 5 𝑂 5𝐶𝐻3 𝐶𝑂𝑂𝐻 + (𝐶𝐻𝑂𝐶𝑂𝐶𝐻3 )4
| 𝐶𝐻3 − 𝐶𝑂 |
𝐶𝐻2 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐶𝑂𝐶𝐻3
Acetic Anhydride Glucose Penta-Acetate

6. Presence of Primary Alcoholic Group

𝐶𝐻𝑂 𝐶𝑂𝑂𝐻 𝐶𝑂𝑂𝐻

| | |
𝐶𝑜𝑛𝑐 . 𝐻𝑁𝑂3 𝐶𝑜𝑛𝑐 .𝐻𝑁𝑂3
(𝐶𝐻 − 𝑂𝐻)4 (𝐶𝐻 − 𝑂𝐻)4 (𝐶𝐻𝑂𝐻)4
| | |
𝐶𝐻2 − 𝑂𝐻 𝐶𝑂𝑂𝐻 𝐶𝐻2 − 𝑂𝐻
Saccharic Acid Gluconic Acid

On oxidation with 𝐶𝑜𝑛𝑐. 𝐻𝑁𝑂3 , glucose as well as gluconic acid both yield a dicarboxylic acid
[Saccharic Acid]. This indicates the presence of a primary alcoholic (−𝑂𝐻) group in Glucose.

7. Special Arrangement of (−𝑶𝑯) group

The exact special arrangement of 5(−𝑂𝐻) group in glucose was provided by Fischer. After
studying many other properties of it.
𝐶𝐻𝑂
|
𝐻 − 𝐶 − 𝑂𝐻
|
𝐻𝑂 − 𝐶 − 𝐻
| 𝑫 −⊕ −𝑮𝒍𝒖𝒄𝒐𝒔𝒆
𝐻 − 𝐶 − 𝑂𝐻
|
𝐻 − 𝐶 − 𝑂𝐻
|
𝐶𝐻2 − 𝑂𝐻

Limitation of Open Chain Structure of Glucose

The open chain structure of glucose explains most of the properties of glucose except followings:

(i) Although glucose has an aldehyde group but it doesn’t given 2, 4 − 𝐷𝑁𝑃 test, Schiff test.
(ii) It doesn’t react with 𝑁𝐻3 and 𝑁𝑎𝐻𝑆𝑂3 .
(iii) The penta-acetate of glucose do not react with 𝑁𝐻2 − 𝑂𝐻.
(iv) This indicates the absence of (−𝐶𝐻𝑂) group.

Cyclic Structure of Glucose

 The limitation shown by the open chain structure of glucose can be explained by its cyclic
structure.
 It was proposed that glucose can form a 6 −membered ring in which (−𝑂𝐻) at 𝐶5 can add to
the (−𝐶𝐻𝑂) group and can form a Cyclic Hemiacetal Structure.
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 𝜶 − 𝑫 −⊕ −𝑮𝒍𝒖𝒄𝒐𝒔𝒆 𝜷 − 𝑫 −⊕ −𝑮𝒍𝒖𝒄𝒐𝒔𝒆

Anomers

NOTE
Anomers
The two cyclic hemiacetal structure of glucose differ only in configuration of hydroxyl group
at 𝐶1 called anomeric 𝐶 and these structures are called anomers.

NOTE
The 6 −membered cyclic structure of glucose is called pyranose structure. This cyclic structure of
glucose is more correctly represented by Haworth.

Fructose (𝑪𝟔 𝑯𝟏𝟐 𝑶𝟔 )

𝐶𝐻2 − 𝑂𝐻
|
𝐶𝑂
|
(𝐶𝐻 𝑂𝐻)3
|
𝐶𝐻2 − 𝑂𝐻

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Open –Chain Structure of Fructose
𝐶𝐻2 − 𝑂𝐻
|
𝐶=𝑂
|
𝐻𝑂 − 𝐶 − 𝐻
|
𝐻 − 𝐶 − 𝑂𝐻
|
𝐻 − 𝐶 − 𝑂𝐻
|
𝐶𝐻2 − 𝑂𝐻

 Like Glucose i.e., 𝛼 − 𝑑 −⊖ −fructofuranose and 𝛽 − 𝑑 −⊖ −fructofuranose, the 5 −membered

cyclic structure of fructose formed by the involvement of (−𝑂𝐻) at 𝐶5 and carbonyl group. The
5 −membered ring of fructose is named as furanose.

𝜶 − 𝑫 −⊖ −𝐟𝐫𝐮𝐜𝐭𝐨𝐟𝐮𝐫𝐚𝐧𝐨𝐬𝐞 𝜷 − 𝑫 −⊖ −𝐟𝐫𝐮𝐜𝐭𝐨𝐟𝐮𝐫𝐚𝐧𝐨𝐬𝐞

Anomers

Disaccharides
They are composed of 2 units of monosaccharides on hydrolysis with dilute acid or specific enzyme.

𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
Sucrose 𝛽 −Fructose 𝛼 −Glucose

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 𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
Lactose 𝛽 −Glucose 𝛽 −Galactose
(Milk Sugar)

𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
Maltose 𝛼 −Glucose 𝛼 −Glucose

 In disaccharides, [The two monosaccharide unit are joined together by an oxide linkage
formed by loss of a water molecule and this linkage is known as Glycosidic Linkage]

Sucrose

𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
𝛼 −Glucose 𝛽 −Fructose

Sucrose is formed by the Glycosidic linkage between 𝐶1 of 𝛼 − 𝐷 −Glucose and 𝐶2 of 𝛽 − 𝐷 −Fructose.

 As the reducing part of glucose and fructose are involved in Glycosidic Linkage. So, sucrose
is a non-reducing sugar.
 Thus, the hydrolysis of sucrose change the sign of rotation from dextro-⊕ to lalvo-⊖ and the
product so formed is known as Invert Sugar.

Maltose

𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
𝛼 −Glucose 𝛼 −Glucose

Maltose is formed by Glycosidic Linkage between 𝐶1 of 1 𝛼 − Glucose unit to 𝐶4 of another

𝛼 −Gulcose unit.

 Maltose is a reducing sugar because 𝐶1 of 2nd Glucose unit is involved in not Glycosidic
Linkage. So, it’s a reducing sugar.
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 Lactose

𝐻+
𝐶12 𝐻22 𝑂11 + 𝐻2 𝑂 𝐶6 𝐻12 𝑂6 + 𝐶6 𝐻12 𝑂6
Lactose 𝛽 −Glucose 𝛽 −Galactose

Lactose is formed by Glycosidic Linkage between 𝐶1 of 𝛽 −Galactose to 𝐶4 of 𝛽 −Gulcose unit.

 It is a reducing sugar.

Polysaccharides
A long chain polymer of monosaccharide joined together by Glycosidic Linkage.
E.g. Starch (𝐶6 𝐻10 𝑂5 )𝑛 , Cellulose

STARCH
It is a combination of 2 polysaccharide amylose and amylopectin.

 Amylose
A linear polymer of 𝛼 − 󒊕𝐷 −⊕ Glucose

 Amylopectin
It is the branched chain polymer of 𝛼 − 𝐷 Glucose unit in which chain is formed 𝐶1 to 𝐶4
Glycosidic Linkage whereas branching occurs by 1, 6 −Glycosidic Linkage.

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 Cellulose
 Polymer of 𝛽 − 𝐷 −Glucose

Amino Acids

-NH2 -COOH

Those organic compounds which contain at least one carboxylic group (−𝐶𝑂𝑂𝐻) and one amino
group (−𝑁𝐻2 ) are called amino acids.

→ These amino acid show acidic and basic property at same time.

−𝐻
E.g. 𝑅 − 𝐶𝐻2 − 𝐶𝑂𝑂𝐻 𝑅 − 𝐶𝐻 − 𝐶𝑂𝑂𝐻
+𝑁𝐻2

𝑁𝐻2
Amino Acid
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 −𝐻
𝐶𝐻3 − 𝐶𝑂𝑂𝐻 𝐶𝐻2 − 𝐶𝑂𝑂𝐻
+𝑁𝐻2
Acetic Acid
𝑁𝐻2
Glycine
[𝛼 − 𝑎𝑚𝑖𝑛𝑜 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑]

 Classification of 𝒂𝒎𝒊𝒏𝒐 𝒂𝒄𝒊𝒅 on basis of number of (−𝑵𝑯𝟐 ) group and (−𝑪𝑶𝑶𝑯) group
1. Neutral amino acid (−𝑁𝐻2 = −𝐶𝑂𝑂𝐻)
2. Acidic amino acid (−𝐶𝑂𝑂𝐻 > −𝑁𝐻2 )
3. Basic amino acid (−𝑁𝐻2 > −𝐶𝑂𝑂𝐻)

 Classification of amino acid on basic of needs

1. Essential Amino Acid

Those amino acid which can’t be synthesized in the body and must be obtained through diet
are known as essential 𝑎𝑚𝑖𝑛𝑜 𝑎𝑐𝑖𝑑.
E.g. Leucine, Lysine, Valine (𝐿, 𝐿, 𝑉)

2. Non-Essential amino acid

Those amino acid which can be synthesized in body.
E.g. Alanine, Aspartic Acid, Glycine

 Stereochemistry of Amino Acid

In most of the amino acid, amino group is present at the 𝛼 − 𝐶 atom. Thus, they have the
structure.

𝑅 − 𝐶𝐻 − 𝐶𝑂𝑂𝐻
|
𝑁𝐻2 𝛼 −Amino Acid

E.g. 𝐻 − 𝐶𝐻 − 𝐶𝑂𝑂𝐻 [Glycine]

|
𝑁𝐻2

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 𝐶𝐻3 − 𝐶𝐻 − 𝐶𝑂𝑂𝐻 [Alanine]
|
𝑁𝐻2
NOTE
P
|
𝑆 −C−𝑄 ⇒ Assymetric/Chiral
|
R

 Except glycine all amino acid contain an asymmetric 𝐶 − atom and can show optical
isomerism and can exist into 𝑑 and 𝑙 −form.

 𝐶𝐻3 − 𝐶𝐻 − 𝐶𝑂𝑂𝐻
| [Alamine]
𝑁𝐻2

 Acid-Base behavior of amino acid [Zwitterions]

o In aqueous solution, the (−𝐶𝑂𝑂𝐻) group can lose a proton [𝐻 + ] and (−𝑁𝐻2 ) group can
accept 𝐻 + giving rise to a dipolar ion known as Zwitterions. This is neutral but have
positive and negative charge.
o They have high 𝑚. 𝑝.
o They are soluble in water and insoluble in organic solvent because amino acid
molecules are dipolar.

𝑅 − 𝐶𝐻 − 𝐶𝑂𝑂𝐻 𝑅 − 𝐶𝐻 − 𝐶𝑂𝑂−
𝒂𝒒𝒖𝒆𝒐𝒖𝒔 𝒔𝒐𝒍𝒖𝒕𝒊𝒐𝒏
| |
⇌
𝑁𝐻2 𝑁 + 𝐻3
Zwitter ion

Proteins
+
𝐻 𝑜𝑟
𝑃𝑟𝑜𝑡𝑒𝑖𝑛 + 𝐻2 𝑂 𝐴 𝑀𝑖𝑥𝑡𝑢𝑟𝑒 𝑜𝑓 𝛼 − amino acid
𝑆𝑝𝑒𝑐𝑖𝑓𝑖𝑐 𝐸𝑛𝑧𝑦𝑚𝑒

Proteins on hydrolysis with 𝑑𝑖𝑙. 𝐻2 𝑆𝑂4 or enzyme gives a mixture of 𝛼 − amino acid.

 This shows that protein is formed by the 𝛼 − amino acid i.e., protein is a polymer of 𝛼 −
amino acid and they are connected to each other by peptide linkage [−𝐶𝑂 − 𝑁𝐻−]

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  Dipeptide is formed by the condensation of 2 molecules of 𝛼 − amino acid and tri-peptide is
formed by the condensation of the 3 molecules of 𝛼 − amino acid. Similarly, one obtained by
condensation of more than 10 moleucle of 𝛼 − amino acid is called as Polypeptide.

E.g. NH2-CH2-COOH + NH2-CH2-COOH

Glycine Glycine
−𝐻2 𝑂

NH2-CH2-CO-NH-CH2-COOH

Di-peptide
Linkage

CH3
|
 NH2-CH2-COOH+H2N-CH-COOH+H2N-CH2-COOH

−2𝐻2 𝑂

CH3
|
H2N-CH2-CO-NH-CH-CO-NH-CH2-COOH

Tripeptide Linkage

 A polypeptide with more than 100 amino acid residues having molar mass higher than
10,000 𝑢 is called a protein.

NOTE
51 amino acid ⇒ Insulin [Exception]

Classification of Proteins on basis of their Molecular Shape

1. Fibrous Protein
2. Globular Protein

1. Fibrous Protein
When polypeptide chain run parlled and are held together by 𝐻 and disulphide bond and
form fiber like structure.
 They are insoluble in water.

(i) 𝜶 −Helix Structure

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 (ii) 𝜷 −Pleated Structure

Enzymes
1. Specific catalyst for a biological reaction.
2. Enzyme act on their specific substrate.
3. All enzymes are globular proteins [Soluble in 𝐻2 𝑂]
4. Name of enzyme is generally originated from their source.

𝐻+
𝑆𝑢𝑐𝑟𝑜𝑠𝑒 + 𝐻2 𝑂 𝛼 − 𝐺𝑙𝑢𝑐𝑜𝑠𝑒 + 𝛽 − 𝐹𝑟𝑢𝑐𝑡𝑜𝑠𝑒
𝑆𝑢𝑐𝑟𝑎𝑠𝑒 𝑜𝑟 𝐼𝑛𝑣𝑒𝑟𝑡𝑎𝑠𝑒

𝐻+
𝐿𝑎𝑐𝑡𝑜𝑠𝑒 + 𝐻2 𝑂 𝛽 − 𝐺𝑙𝑢𝑐𝑜𝑠𝑒 + 𝛽 − 𝐺𝑎𝑙𝑎𝑐𝑡𝑜𝑠𝑒
𝐿𝑎𝑐𝑡𝑎𝑠𝑒

𝐻+
𝑀𝑎𝑙𝑡𝑜𝑠𝑒 + 𝐻2 𝑂 𝛼 − 𝐺𝑙𝑢𝑐𝑜𝑠𝑒 + 𝛼 − 𝐺𝑙𝑢𝑐𝑜𝑠𝑒
𝑀𝑎𝑙𝑡𝑎𝑠𝑒

𝐻+
𝑈𝑟𝑒𝑎 𝑁𝐻3 + 𝐶𝑂2
𝑈𝑟𝑒𝑎𝑠𝑒

𝐻+
𝑆𝑡𝑎𝑟𝑐ℎ 𝛼 − 𝐺𝑙𝑢𝑐𝑜𝑠𝑒
𝛼 − 𝑎𝑚𝑦𝑙𝑎𝑠𝑒

 Enzyme also increase the rate of reaction by providing a mechanism of lower 𝐸𝑎

𝐸𝑎 = 6.2 𝐾𝐽 𝑚𝑜𝑙 −1

𝐻+
Sucrose + 𝐻2 𝑂
Invertase
𝐸𝑎 = 2.15 𝐾𝐽 𝑚𝑜𝑙 −1

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Vitamins
They are organic compounds which are essential for normal growth of life for animals, some
bacteria and micro-organisms. Vitamins are not synthesized by animals [except vitamin 𝐷]
 Vitamins are supplied to the organism through diet.

Classification of Vitamins

1. Water Soluble
Vitamins 𝐵 and 𝐶 are water soluble.
⇒ They must be supplied regularly in diet because they are readily excreted by in urine and can’t be
stored in our body except Vitamins 𝐵12 [Cyanocobal Amine]

2. Fat Soluble
Vitamins which are soluble in fat and oils but insoluble in 𝐻2 𝑂.
⇒ They are Vitamins 𝐴, 𝐸, 𝐷 and 𝐾.
⇒ They are stored in liver and adipose tissues [Fat Storing]

Nucleic Acid
The particle present in the nucleus of the cell which is responsible for heredity is known as
chromosome.

 They are made of some protein and other compound known as Nucleic Acid.

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 𝐻2 𝑂 / 𝐻 +
Nucleic Acid Pentose Sugar + Phosphoric Acid + Bases

DNA RNA
[Deoxyribose Nucleic Acid] [Ribose Nucleic Acid]

1. Adenine 1. Adenine
2. Guanine 2. Guanine
3. Thymine 3. Uracil
4. Cytosine 4. Cytosine

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