Carbohydrate metabolism

Cho are compounds which are aldehyde or ketones derivative of

polyhydroxy(eg. 3 OH groups, glycerol) alcohols

Glyceraldehyde

It's the first parent compound

criteria for carbohydrate classification

Hydrolysis of the carbohydrate compound leading to conversion into

simple carbohydrate which are monosaccharides

Count the no. of monosaccharide units which determines the class of the
carbohydrate

Four classes

1. Monosaccharides, can not be hydrolyzed further

2. Disaccharides, two unit of monosaccharide needed

3. Oligosaccharide, 3-10 monosaccharide 🌟

4. Polysaccharide, >10 monosaccharide

Monosaccharide

Molecular formula

Above is the chemical or molecular formula for monosaccharide only

Aka empirical formula

n is the no. of Carbon atoms

Value lies between 3-9(don't confuse with 3-10 C of oligosachharide )

3 triose

4 tetrose

5 pentose

6 hexose

7 heptose

8 octose

9 nanose
Isomers of Carbohydrates

Isomers: same molecular, chemical or empirical formula but different

structural formula

Structural formula depicts the exact location in space of different

elements

5 different types

1. Aldose and ketose isomerism

2. Epimers

3. Pyranose and Furanose ring structure

4. Alpha and ß anomers

5. D and L type

Epimers

Glucose and Galactose are C4 epimer of each other

Glucose and mannose are C2 epimers of each other

Galactose and mannose have same formula but not epimer of each other

glucose and galactose only differ at no. 4

Glucose and mannose differ at position 2

epimers are those isomers where hydroxyl differs on the structure on one
of the asymmetric C atoms

Asymmetric C atoms: all 4 valencies are attached to different moieties

Pyranose and Furanose ring structure

Pyranose: heterocyclic hexacyclic ring structure

Furanose: heterocyclic pentacyclic ring structure

Glucose

the linear structure shown before are present in dry state

In water, they form a closed cyclic form which could either be pyranose or
Furanose

C1 and C5 condense in glucose to form a pyranose

the glycosidic bond is formed which closes the ring structure

to form Furanose, C1 and C4 are involved, 4th hydroxyl is contributed

while 5th in pyranose

Whenever glucose is dissolved, the first or precursor form is Pyranose

Later the pyranose opens up and forms Furanose

And vice versa

Pyranose to Furanose and vice versa

Equilibrium state: rate of forward reaction is equal to reverse reaction

Thus constant concentration at each side of reaction

99% glucose remains in Pyranose form and 1% remains in Furanose form

at equilibrium

All the things applicable for glucose is applicable to galactose and

mannose as well

For fructose

There are some variations

Fructose also initially forms all pyranose

2nd C is involved instead of C1

Thus C2 and C6 are involved in forming the pyranose

thus in Furanose, C2 and C5 are involved in making the ring structure

Anomeric forms

Alpha and ß forms

To deduce the different forms, find the anomeric C atom

Anomeric is the C atom which is having the reactive group for

condensation process

If hydroxyl of anomeric C atom is above the plane of ring, ß form

If below, alpha form

Eg.

Glucose

When dissolved in water

Initial forms are all alpha forms

After 12 hours

Ripening of glucose solution

The predominant form is ß form (2/3)

Alpha is (1/3)

This process is called Mutarotation

Optical activity is changed due to this, thus the name

Optical activity is 114 degree of fresh glucose solution

After 12 hours, the optical activity is decreased to 52.5 degrees

Alpha form has optical activity of 114

ß form has 19 degree optical activity

Mutarotation does not change dextrorotatory to levorotatory

D and L isomer aka enantiomers

Penultimate C atom is seen, if hydroxyl on right side, D form

If on left side, L form

Glucose is two types: D and L

Both are dextrorotatory

Optical isomerism denoted by lower case d and l

Thus both glucose forms are d

Thus the D and L are not optical isomers

All monosaccharides are reducing

Hemiacetal and hemiketal group are responsible for the reducing

tendency

Sometimes they are lost in bond formation and the disaccharide loses it's
reducing tendency

Disaccharides

Follow the Workbook

Oligosaccharide
3-10 C atoms

Maltotriose
Total misnomer

Since it has 3 monosaccharide and not 3 carbon atoms

And maltose is a disaccharide

Some are Cell wall constituent

These are Antigenic in nature

Involved in receptor activity

Polysaccharide

Homopolysaccharide: same components

Follow the workbook

Iodine attaches at the non reducing end

It tells is about the branching of the molecule

Heteropolysaccharide: different components

Eg. Mucopolysaccharide MPS

6 MPS

1. Hyaluronic acid

2. Heparin

3. Heparan sulfate

4. Chondroitin sulfate

5. Dermatan sulfate

6. Keratan sulfate (don't confuse with keratin which is a protein)

All have a structural characteristic

They are made up of disaccharide units in a linear fashion with lot of

sulfation

Each disaccharide is made up of Uronic acid and amino sugar

These are derived from monosaccharide , replacement of amino group

What is Uronic acid

It is the oxidized form of the monosaccharide

Glucose oxidase peroxidase method for glucose estimation

GOD POD method

Gluconic acid is formed in this reaction

Hyaluronic acid has no sulfation 💥

Keratan sulfate does not have Uronic acid

One amino sugar and one plain sugar instead of Uronic acid

Functions of mucopolysaccharides

1. Turgidity to the extracellular matrix

2. hygroscopic

3. Poly anions , have negative charge

4. Forming proteoglycans( complex structure consisting of protein and

MPS)

In glycoprotein , simple carbohydrate is there, not complex carbohydrate

like MPS

Proteoglycans and the glycoproteins

Glycoprotein: proteins that contain oligosachharide chains( glycans)

covalently attached to the polypeptide backbone

Function. Glycoprotein

Structure: collagen

Lubricant: mucin

Transportation: transferrin, ceruloplasmin

Immunity: Ig, histocompatibilty Ag

Hormone: HCG, TSH

Enzymes: ALP

Receptor: hormone and drug action

Chaperones: calnexin, calreticulin

Antifreeze : plasma protein of cold water fish

Interact with specific carbohydrate : lectins, Selectins

Three major classes of glycoproteins

1. Containing O glycosidic linkage

Involving the hydroxyl side chain of Serine or threonine and a sugar such
as N acetyl galactosamine ( GalNac-Ser(thr))

2. Containing N glycosidic linkage

Involving the amide nitrogen of asparagine and N acetylglucosamine

3. GPI linked glycoprotein

Glucosyl phosphatidyl inositol

Proteoglycans

Proteins that contain covalently linked glycosaminoglycans

Syndecan, betaglycan, serglycin, perlecan, aggrecan, versican, decorin,

Bottle brush appearance

Caterpillar appearance

Glycolysis

All cells all the time

Aerobic and anerobic( one extra step)