Biocatalysis IQS

BIOTECHNOLOGICAL PRODUCTS AND PHARMACEUTICALS
Academic year 2022-23

4th year, Biotechnology Grade
1st semester
Part I. (Dr. Ciril Jimeno).
1. Biocatalysis. Chirality in Nature.

2. Synthesis and catalysis: concepts.
3. Classification of enzymes and enzymatic reactions. Basic mechanisms.
5. Production of bulk chemicals.
6. Fine chemicals and agrochemicals.
7. Production of pharmaceuticals.
8. Production of food additives.
Part II. (Dr. Teresa Pellicer)
4. Industrial production of biocatalysts and proteins.

9. Vaccines.
10. Monoclonal antibodies.
11. Bioplastics.
12. Vitamins.
1
BIOTECHNOLOGICAL PRODUCTS AND PHARMACEUTICALS
Academic year 2022-23
4th year, Biotechnology Grade
1st semester
Part I. (Dr. Ciril Jimeno).

2. Synthesis and catalysis: concepts.
3. Classification of enzymes and enzymatic reactions. Basic mechanisms.
5. Production of bulk chemicals.
6. Fine chemicals and agrochemicals.
7. Production of pharmaceuticals.
8. Production of food additives.
Part II. (Dr. Teresa Pellicer)
4. Industrial production of biocatalysts and proteins.

9. Vaccines.
10. Monoclonal antibodies.
11. Bioplastics.
12. Vitamins.
2
1. BIOCATALYSIS. CHIRALITY IN NATURE.
BIOCATALYSIS: Catalysis using a biocatalyst, this is, enzymes, cells

or living organisms.
Enzymes are the ultimate biocatalysts!
Pros of biocatalysis: (1) Mild reaction conditions (T, pH, aqueous environment,
open air).
(2) Huge adaptability and ability to modification.
(3) Stereoselectivity (control of the 3D structure of the
molecules).
Cons of biocatalysis: (1) Expensive and long development (unless wild types
can be used).
(2) Limited reaction conditions (enzymatic stability).
What type of products can be obtained through biotechnology?

1.Bulk chemicals (Commodities)
2.Fine chemicals.
3.Specialty chemicals.
4.Pharmaceuticals.
3
1.1 BULK CHEMICALS (COMMODITIES).

Million tons per year.
Continuous (flow) production.
Multiple applications ➔ Huge world demand.
Low price.
Ex.: Acetic acid (AcOH) ➔

6.5 million tons/year
Ancient biotech
process.
4
1.1 BULK CHEMICALS (COMMODITIES).
 There is always a competition between biotechnological and chemical processes.

 Sometimes both biotech and chemical processes are operational at the same time.
 The winner depends on price and/or quality (specifications).
Ex.: Acetic acid (AcOH) ➔

6.5 million tons/year
Ancient biotech
process.
5
1.2 FINE CHEMICALS.
Production typically <1000 tons/year.
Batch production.
Biotech processes gain importance.
Fine chemicals require definite specifications because they are

meant for a very particular effect in a final product.
They are intermediates: starting materials for pharmaceuticals and

specialty chemicals.
6
1.2 FINE CHEMICALS.
Ex.: Production of enantiomerically pure piperazino-2-carboxylic acid.

(Kinetic Resolution –KR)
7
1.3 SPECIALTY CHEMICALS.
AKA effect chemicals, performance chemicals or formulation chemicals ➔

➔ Final products.
Meant for a definite application.
They can be single products or mixtures (formulations).

Examples:
Made from fine chemicals. Adhesives and glues.
Tensioactives, detergents, cleaning
Batch production. products.
Elastomers (rubber).
Cosmetic additives.
Flavors and scents.
Food additives.
Lubricants.
Inks, coatings, dyes.
Agrochemicals.
8
1.3 SPECIALTY CHEMICALS.

AKA effect chemicals, performance chemicals or formulation chemicals
Ex.: Biotech production of (S)-malic acid.

Malic acid is an acidifier for fruit and vegetal juices, soda beverages,
marmalades and jams, and sweets.
Also used in the treatment of liver malfunction.
9
1.4 PHARMACEUTICALS.
Medicines and drugs to treat illness. They are also final products.
Very strict specifications and regulations ➔ Regulatory Pharma.

Food and Drug Administration (FDA - USA).
Pharmacopoeia Europaea (EU).
Made from fine chemicals.
Batch production.
10
1.4 PHARMACEUTICALS.
Ex.: Preparation of (S)-ibuprofen (Kinetic Resolution -KR).

Non-steroidal anti-inflammatory.
The (S) enantiomer is 100 times more potent than the (R).
11
CHIRALITY.
Geometric property of matter.
An object is chiral when it cannot be superposed to its mirror image ➔

➔ No internal symmetry plane.
12
CHIRALITY.
Geometric property of matter.
An object is chiral when it cannot be superposed to its mirror image ➔

➔ No internal symmetry plane.
External symmetry plane
Macroscopic
chirality:
13
CHIRALITY.
Shells of two different species of sea snail: on

the left is the normally sinistral (left-handed)
shell of Neptunea angulata, on the right is the
normally dextral (right-handed) shell
of Neptunea despecta
14
CHIRALITY.
At the biological level, chirality is a fundamental property ➔ One sense of

chirality predominates (one enantiomer).
Ex.: amino acids ➔ L (levo, they turn the polarized light plane to left).
L-Valine
Ex.: Sugars ➔ D (dextro, they turn the polarized light plane to right ).
a-D-glucopyranose
15
CHIRALITY.
Molecular chirality translates into supramolecular

chirality
Secondary and tertiary structure
macromolecules: DNA, proteins are chiral.
16
From atomic to supramolecular chirality: 20 essential amino acids (Chiral !)
17
From atomic to supramolecular chirality: Secondary structures ➔ alpha helix (Chiral!)
Secondary interactions: H bond, electrostatic, VdW

18
From atomic to supramolecular chirality: Tertiary structures ➔ proteins (Chiral !)
Heme group
Myoglobin
(oxygen binding protein in the muscle tissue) 19
As a result, cell metabolism is also chiral ➔ chiral interactions at the molecular level
Keystone in pharmacology ➔ Chiral drugs
Ex. 1:
Vitamine C (ascorbic acid) Shikimic acid

(antioxidant) (key intermediate in plant and
microorganisms metabolism)
20
Ex. 2: Morphine (reduce pain, warm

relaxation, pleasure, very addictive)
Codeine (reduce pain, morphine

prodrug with much lower binding
affinity to opioid receptors)
Papaver somniferum ➔ Opium
(Breadseed poppy)
Heroin (reduce pain, alternate euphoria

and relaxation, pleasure, very addictive)
21
Summary:
22

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BIOTECHNOLOGICAL PRODUCTS AND PHARMACEUTICALS

Academic year 2022-23

Part I. (Dr. Ciril Jimeno).

1. Biocatalysis. Chirality in Nature.

Part II. (Dr. Teresa Pellicer)

4. Industrial production of biocatalysts and proteins.

Part I. (Dr. Ciril Jimeno).

1. Biocatalysis. Chirality in Nature.

Part II. (Dr. Teresa Pellicer)

4. Industrial production of biocatalysts and proteins.

BIOCATALYSIS: Catalysis using a biocatalyst, this is, enzymes, cells

What type of products can be obtained through biotechnology?

1.1 BULK CHEMICALS (COMMODITIES).

Ex.: Acetic acid (AcOH) ➔

1.1 BULK CHEMICALS (COMMODITIES).

 There is always a competition between biotechnological and chemical processes.

Ex.: Acetic acid (AcOH) ➔

1.2 FINE CHEMICALS.

Production typically <1000 tons/year.

Biotech processes gain importance.

Fine chemicals require definite specifications because they are

They are intermediates: starting materials for pharmaceuticals and

1.2 FINE CHEMICALS.

Ex.: Production of enantiomerically pure piperazino-2-carboxylic acid.

1.3 SPECIALTY CHEMICALS.

AKA effect chemicals, performance chemicals or formulation chemicals ➔

Meant for a definite application.

They can be single products or mixtures (formulations).

1.3 SPECIALTY CHEMICALS.

Ex.: Biotech production of (S)-malic acid.

Very strict specifications and regulations ➔ Regulatory Pharma.

Made from fine chemicals.

Ex.: Preparation of (S)-ibuprofen (Kinetic Resolution -KR).

Geometric property of matter.

An object is chiral when it cannot be superposed to its mirror image ➔

Geometric property of matter.

An object is chiral when it cannot be superposed to its mirror image ➔

Shells of two different species of sea snail: on

At the biological level, chirality is a fundamental property ➔ One sense of

Molecular chirality translates into supramolecular

Secondary and tertiary structure

macromolecules: DNA, proteins are chiral.

From atomic to supramolecular chirality: 20 essential amino acids (Chiral !)

From atomic to supramolecular chirality: Secondary structures ➔ alpha helix (Chiral!)

Secondary interactions: H bond, electrostatic, VdW

From atomic to supramolecular chirality: Tertiary structures ➔ proteins (Chiral !)

Keystone in pharmacology ➔ Chiral drugs

Vitamine C (ascorbic acid) Shikimic acid

Ex. 2: Morphine (reduce pain, warm

Codeine (reduce pain, morphine

Heroin (reduce pain, alternate euphoria

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