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Biochemistry
Bio-Organic Bio-Inorganic
Biochemistry
Bio-Organic Bio-Inorganic
Our Focus
Molecules
Important Others
Carbohydrates Lipids
Proteins Vitamins
Examples :
C2(H2O)2
Yet it is a Carbohydrate.
Modern Definition:
(+) D- Glucose
Dextrorotatory Sugar
Source:
Photosynthesis in plant leaf : CO2 + H2O
External Conditions:
❖ Sunlight
❖ Chlorophyll
Chlorophyll is a Metal Ion-Complex of
Mg(Magnesium)
Storage of (+) D- Glucose in
biopolymer
D-Glucose D-Glucose is inter-convertible in
Starch, Glycogen, Cellulose
Starch Cellulose
present in
animals
Classification of Carbohydrates
Functional
Group
Polyhydroxy Polyhydroxy
Aldehyde Ketone
Glucose Fructose
Classification of Carbohydrates
2. On the basis of Reducing Nature:
Reducing Nature
Non-Reducing Reducing
Sugar Sugar
Sucrose Fructose
Lactose, Maltose and Sucrose
Glucose are Dissaccharides
Maltose
Lactose
All monosaccharide
Classification of Carbohydrates
3. On the basis of Sweetness:
Sweetness
Sugar Non-Sugar
3 4 5 6
Triose Tetrose Pentose Hexose
Tetra means Four
–CHO → Aldose •C=O→
Ketose Ose means Sugar
So if a Carbohydrate has 4 Carbons and
-CHO, then it is “ALDO-PENTOSE”
Oligo-Saccharides
2) CHO
(CHOH)4 HI,
CH3–(CH2)4–CH3
Δ
CH2OH (Prolonged) N- hexane
(CHOH)4 CH2OH
HCN
CH2OH CN OH
CH
(Cyanohydrin) (CHOH)4
CH2OH
Carbonyl group present
Evidence of Glucose structure
4) CHO COOH
Presence of Aldehyde group
Br2/H2O
(CHOH)4 (CHOH)4
CH2OH CH2OH
(Glucose) (Gluconic acid)
=
O O
Ac– : CH3 – C – Ac: Acetyl Group
=
O
Anhydride + Alcohol → Ester + Acid Presence of 5 –OH Groups
Conclusion:
Glucose is concluded to have 5 Alcoholic groups and 1 Aldehydic group
all On Different Carbons, as the Structure Is Stable
2 –OH groups on same carbon are unstable all
On Different Carbons
∴ The structure is :
H H H H H H
– –
– –
– –
– –
– –
C – C – C – C – C – C – OH
O OH OH OH OH H
Stereochemistry
The examination of stereochemistry of Glucose was done by Fischer,
and he gave the following structure
CHO
H * OH ⇒ Carbon Backbone
HO * H 4 chiral carbons
H * OH
⇒ 24 = 16 possible
H * OH
configurations exist
CH2OH
1) Glucose DOES NOT SHOW 2-4 DNP test, Schiff’s Base test, NaHSO3 Addition product
Though straight chain on direct reaction forms oxime, cyclic structure doesn’t
Glucose
α- Glucose β -Glucose
Melting Points: 419K 423K
Crystallization of Crystallization of
Concentrated solution Hot and saturated
Preparation: Of Glucose at 303K solution at 371K
(300C) (980C)
Room Boiling Point
Temperature of Water
Cyclised structure of Glucose
Let us first draw the straight chain structure in center. On cyclisation, If –OH on C-1
comes on right ⇒ α-Glucose; left ⇒ β-Glucose
Glucose
(0.02%)
α-D-Glucose CHO β-D-Glucose
H OH There exists equilibrium, α and
α – cycle HO H β – cycle
(36%) (64%) β forms can interconvert via
H OH
H OH straight chain structure.
1 1
H OH CH2OH HO H
2 2
H OH H OH
3 O HO 3 O
HO 4
H 4
H
H OH H OH
5 5
H H
6 6
CH2OH CH2OH
Proofs of Cyclic Structure
R′ CH OR
2 R–OH + 1 R′–CHO + H–OH
OR
Alcohol Aldehyde Acetal Water
R′ CH OR
1 R–OH + 1 R′–CHO
OH
Alcohol Aldehyde Hemi-Acetal
: :
Lets focus on C1, the O on C5 will attack C1 and will form 6-membered ring.
1
H 2
OH
H OH Configuration of C in -CHO is sp2,
H O
3
HO while in Hemi-Acetal is sp3.
4
H OH
5
H
6
CH2OH
A sp2 C is susceptible to attack from two sides: Above or Below
So we have 2 structures accordingly: α and β
If -OH at C1 is inside the box like structurethen, it is α and if outside then β
Observation
α and β forms are Epimers of each other, at C1.
Anomers :
Anomer is a special type of epimer that differs in
configuration, specifically at the
hemiacetal /acetal carbon atom.
Eg. α-D-glucopyranose and β -D-glucopyranose
6 6
CH2OH CH2OH
H
5 O H H
5 O
H H
4 1 4 1
HO OH H HO OH H
OH
3 2 3 2
H OH H OH
α-D-Glucose β-D-Glucose
The two cyclic forms α and β are in equilibrium with the open chain structure.
Anomers
6
CH2OH 6
CH2OH
H
5 O H 5 O OH
H H H
4 1 4 1
HO OH H OH H
OH HO H
3 2 2
OH 3
H H OH
α-D-Glucose β-D-Glucose
α-D-(+)-Gluco-Pyranose β-D- (+)-Gluco-Pyranose
Specific Rotation of
α-D-Glucopyranose: +112.2°
β-D-Glucopyranose: +18.7°
Optical activity at equilibrium : +52.6°
Fructose
❑ Keto-hexose
❑ Laevose
Structure 1
CH2OH
2 O
3
HO H
4
H OH
5
H OH
6
CH2OH
HOH2C 6 1 HOH2C 6 OH
O CH2OH O
5 H HO 2 5 H HO 2
H 4 H 4 1
3 OH 3 CH2OH
OH H OH H
α-D-(–)-Fructo-furanose β-D-(–)-Fructo-furanose
Example :
1) Sucrose
2) Maltose
3) Lactose
6 CH2OH
Sucrose 5 O HOH2C 6 O OH
H H H
5 H HO 2
4 1 1
HO OH H OH H 4
3
CH2OH
3 2 OH OH H
H
α-D-Glucose β-D-Fructose
α _ β _ Glycosidic linkage
Sucrose
α _ β _ Glycosidic linkage
Glucose Hemi-Acetal
Hence, they give Tollen’s,
Fructose Hemi-Ketal Benedict’s and Fehling’s test.
Amylose
STARCH
Amylopectin
GLYCOGE
N
CELLULOSE
Properties of Amylose and Amylopectin
Amylose Amylopectin
6 6
CH2OH CH2 OH
H
5 O H H
5 O H
H 1
H 1
4 4
OH H OH H
O 2
O 2
O
3 3
H OH H OH
Amylopectin
6 6
CH2OH CH2OH
H
5 O H H
5 O
H H H
1 4 1
4
OH H OH H
O O
H
3
OH
2 3
H OH
2
O
6 6
CH2OH CH2
H
5 O H H
5 O H
H 1
H 1
4 4
OH H OH H
O 2
O 2
O
3 3
H OH H OH
Cellulose It is a Straight chain polysaccharide composed only of Beta D-
Glucose 6
CH2OH
H H
5 O OH
4 1
OH H
6
H
CH2OH 3 2
H OH
H
5 O OH
H
4 1 β-D-Glucose
OH H
H
3 2
6
CH2OH H OH
H
5 O OH β-D-Glucose
H
4 1
OH H
H
3 2
H OH
β-D-Glucose
Glycogen
it is also called Animal Starch. Its Structure is similar to Amylopectin & rather
more highly branched..
6 6
CH2OH CH2OH
H
5 O H H
5 O
H H H
1 4 1
4
OH H OH H
O 3 2
O 3 2
H OH H OH
6 6
CH2OH CH2
H
5 O H H
5 O H
H 1
H 1
4 4
OH H OH H
O 2
O 2
O
3 3
H OH H OH
Proteins (Greek word Proteios)
Residue of H
Amino acid
C
COOH
R
NH2
Amino Iso-Propyl Iso-Butyl
acids CH3
–
R H– CH3– (CH3)2CH– (CH3)2CH.CH2– CH3–CH2–CH– Sec-Butyl
Name Glycine Alanine Valine Leucine Isoleucine
Symbol Gly Ala Va Leu Ile
l
Code G A V L I
COOH COOH
H * NH2 NH2 * H
R right left R
D – Amino acid L - Amino acid
Classification of Amino Acids
Essential Non–Essential
x• x=y .y
y
Colorless
–
R–CH–COO
⇒ Zwitter Ion
–
+
NH3
H
Gylcine
Zwitter Ion
– H+ – H+
R–CH–COO R–CH–COO R–CH–COOH
–
–
+ +
NH2 NH3 NH3
:
OH OH
K1 K2
Basic medium ⇒ Goes towards Carboxyl ion
Acidic medium ⇒ Goes towards Ammonium ion
O
H2N CH C NH CH COOH
H CH3
Gly Ala
Proteins
A Poly-Peptide with more than 100 Amino Acid Residue,
with molar mass > 10,000 amu(D) is called a protein.
Proteins > 10 kD
EXCEPTIONS are possible
Example
Insulin has only 51 Amino Acid Residues.
Molecular Shape of Proteins :- It can be classified in 2 types
Structure of Proteins
The structure and shape of protein can be studied at four different levels:
Secondary
It describes the shape in which Secondary structure arises due to folding of the
polypeptide chain can exist back bone of the polypeptide chain to H–bonds.
Two types can exist
α–helix β-pleated–sheets
Quaternary Structure
of Haemoglobin
Denaturation of Protiens
Phosphate ester
Ribose CHO
H OH
Cyclic Structure: H OH
H OH
CH2OH
HOH2C 5 O OH HOH2C 6 H
O
4 H H 1 4 H H 1
H 3 2 H H 3 OH
2
OH OH OH OH
β-D-Ribo-Furanose α-D-Ribo-Furanose
Nitrogenous
base
Derivative of Derivative of
Purine Pyrimidine Usually Heterocyclic
6 7 6
1
5 N 1 5
N N
8
2 4 N9 4
2
N
3
N3
6 7 6 7
1
5 N 5 N
N 1
N
8
8
2 4 N9 2 N9
N N
4
3
3
NH2 O
6 7 6 7
H
1
5 N 1
5 N
N N
8
8
2 N9
2
N 4 N9 H2N 4
N
3 3
Guanine
Adenine
66
1 5
N
2 4
N3
Pyrimidine
NH2
6 OH O
1 5 6 6
N H 1 5 H 1 5 CH3
N N
4
O 2
N3 O 2 4
O 2 4
N3 N3
H
H H
Cytosine
Uracil Thymine
O
Phospho Ester
P
Nucleic Acids contain only HO OH
OH
Phosphoric acid
O O
Phospho-mono-ester P Phospho-di-ester P
RO OH RO OR
OH OH
O
Phospho-tri-ester
P
RO OR
OR
Nucleosides
Nucleotides
5′
5′ HOH2C O
HOH2C O OH
4′ 1′
4′
H H 1′
Adenosine
H H
H 3′ 2′
H
H 3′ H
2′ OH OH
OH OH
β-D-Ribose Constituents of Adenosine
Nucleosides Constituents ofDeoxy-Adenosine
NH2
6 7 NH2
6 7
1
5 N
N 5 N
8
Adenine 1
N
8
2 4 N9
N 2 4 N9
3 N
H 3
2′-Deoxy-Adenosine
5′
HOH2C O OH 5′
HOH2C O
4′ 1′
H H 4′ 1′
H H
H 3′ H
2′ H 3′ 2′
H
OH H
OH H
2′-Deoxy-Ribose
Nucleotides
HO 4′
1′ P 5′
O
1′
O– O 4′
3′ 2′ O– 3′
OH OH 2′
OH OH
DNA and RNA
Nucleic Acids
RNA DNA
Ribose 2′-Deoxy-Ribose
DNA and RNA
DNA
RNA
3′ 2′
3′ 2′
In which the two helices are bound together by H–bonds between bases.
Sugar and Phospho groups appear to form Rails and the Bases appear to form Rungs.
Complementary bases
In DNA, bases do not randomly pair up with each other,
but there are fixed pairs that pair up in double strands,
Complementary
Bases
Adenine Guanine
Thymine Cytosine
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