Development in biocatalysis for organic chemistry

1. Presented by:
Amrendra Kumar
Dept of Medicinal Chemistry
MC/2022/01
NIPER Hyderabad
Development in Biological catalysis for Organic
Chemistry
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2. Introduction
Classification of Biocatalyst
Advantages of Biocatalyst
Beginning of Biocatalyst
Case study
Application
Future Prospects
Conclusion
References
Contents
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3. • Berzelius coined the term catalysis in 1836
• Kuhne in 1878 coined the term enzyme
• Catalyst: Those agents which catalyze the reaction are called as
Catalyst
• Enzymes: Those catalysts which catalyze the biochemical
transformation are called as Enzymes. Ex- lipase, ligase, etc.
Biocatalysis may be defined as the use of natural substances that
include enzymes from biological sources or whole cells to
catalyze or speed up chemical reactions are called as biocatalysis.
Introduction
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4. Why fireflies light up at night & jellyfish glow?
In abdominal part of fireflies , following reactions takes place which is responsible
for lighting.
Examples of Biocatalyst in Living cells
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5.  Different enantiomer(R&S) have different
biological interaction
 Such obstacles can be overcome by use
of biocatalysts or enzymes since they are
substrate specific
 Sustainable green chemistry
 Useful tools in asymmetric synthesis
Why Bio-catalysis in Organic Chemistry or Synthesis?
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6. Enzyme class Enzyme type Examples Reaction catalysed
EC1 Oxidoreductase Oxygenase, Oxidase,
Peroxidase, Dehydrogenase
Oxidation & Reduction
EC2 Transferase Transaminase,
Glycosyltransferase
Transfer of a group from one
molecule to another
EC3 Hydrolase Lipase, Protease, Esterase,
Nitrilase, Hydralase
Hydrolysis
EC4 Lyase Decarboxylase, Dehydratase Non-hydrolytic bond cleavage
EC5 Isomerase Racemase & Mutase Intermoleculer rearrangement
EC6 Ligase DNA ligase Bond formation requiring
triphosphate
Classification of Bio-catalyst
• This classification was given by the International Union of Biochemistry & Molecular
Biology
• Almost 60% of biocatalysts used are hydrolase in biotransformation
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7. • Speed up the chemical reaction but do not affect the thermodynamic
reaction.
• High selectivity:
Stereo-selectivity(R&S)
Regioselectivity(Positional)
Chemo-selectivity( Functional group-specific)
• Single step in organic synthesis can be accomplished.
• Can be done in an aqueous environment & there is no need for protection
& deprotection.
Advantages of Biocatalyst
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8. Previously, biocatalysts were used in the form of fermentation for the
production of foodstuffs like cheese, beer, vinegar, etc.
In 1958, Louis Pasteur established a big milestone in biocatalysts.
He treated an aq sol of racemic Tartaric acid ammonium salt with a
culture of mold Penicillium Glaucum.
It leads to the consumption of d-tartaric acid & concomitant
enrichment of l-enantiomer.
It was considered the forerunner of enzymatic catalysis kinetic.
Development of biocatalyst in organic chemistry
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9. In first half of 20th century scientist has discovered how to use whole cell, cell
extracts or partially purified enzymes in various biocatalytic process.
In 1913, Ludwig Rosenthaler put forward the preparation of (R)Mandelonitrile
from benzaldehyde.
Emulsin extracted from better almonds.
It was considered to be beginning of modern bio-catalyst mediated asymmetric
catalysis.
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10. Another landmark by Pfizer, Merk & Upjohn:
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This synthesis were given by R.Woodward in 1952
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11. (1) Stereoselective hydrolysis by lipase: Levetiracetam
Case study
>
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12. (2) Cascade synthesis of Vit-B12:
• By use of bio-catalysis, synthetically 17 steps synthesis can be avoided.
• Enzymes used are:
Methyl transferase
S-adenosyl phosphatase
Glutamyl transferase
Methionine synthase Vit B-12
Case study
>
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13. • Synthesis of atorvastatin intermediates: Multifaceted approach
Application of biocatalyst in OCS
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14. • Resolution using Lipase
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15. • Nitrile to amide
• Lonza Process
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16. Systematic use of directed evolution of designed Biocatalyst
The biocatalyst can begin to compete with well-established non-biocatalyst
Multifaceted approach
Enhancement in
E-S affinity
Stability
Higher yield
Future Prospects
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17. Enzymes as a catalyst in OC have a great role:
Biotransformation in several pharmaceuticals
Sustainable chemoenzymatic process
Selectivity
Economical
Green chemistry
Conclusion
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18. 1. M. Bilal et al., “Oxidoreductases as a versatile biocatalytic tool to tackle pollutants for clean environment – a review,” J. Chem. Technol.
Biotechnol., vol. 97, no. 2, pp. 420–435, Feb. 2022, doi: 10.1002/JCTB.6743.
2. T. Kumar Roy, R. Sreedharan, P. Ghosh, T. Gandhi, and D. Maiti, “Ene-Reductase: A Multifaceted Biocatalyst in Organic Synthesis,” Chem. –
A Eur. J., vol. 28, no. 21, p. e202103949, Apr. 2022, doi: 10.1002/CHEM.202103949.
3. Z. Sun, Y. Wikmark, J. E. Bäckvall, and M. T. Reetz, “New Concepts for Increasing the Efficiency in Directed Evolution of Stereoselective
Enzymes,” Chemistry, vol. 22, no. 15, pp. 5046–5054, Apr. 2016, doi: 10.1002/CHEM.201504406.
4. M. Wang, T. Si, and H. Zhao, “Biocatalyst Development by Directed Evolution,” Bioresour. Technol., vol. 115C, p. 117, Jul. 2012, doi:
10.1016/J.BIORTECH.2012.01.054.
5. V. Köhler et al., “Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes,” Nat. Chem., vol. 5, no. 2, pp. 93–
99, Feb. 2013, doi: 10.1038/NCHEM.1498.
6. “Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition - Richard B. Silverman - Google Books.”
https://books.google.co.in/books?hl=en&lr=&id=DS0IBc26RiwC&oi=fnd&pg=PP2&dq=silverman+organic+chemistry&ots=I34vcwDwUS&s
ig=GDofxZHw0wPyZW5WJ3e_atevOgI&redir_esc=y#v=onepage&q=silverman organic chemistry&f=false (accessed Nov. 20, 2022).
7. M. K. Turner, “Biocatalysis in organic chemistry (Part II): present and future,” Trends Biotechnol., vol. 13, no. 7, pp. 253–258, Jul. 1995, doi:
10.1016/S0167-7799(00)88959-3.
8. M. T. Reetz, “Biocatalysis in organic chemistry and biotechnology: Past, present, and future,” J. Am. Chem. Soc., vol. 135, no. 34, pp. 12480–
12496, Aug. 2013, doi: 10.1021/JA405051F/ASSET/IMAGES/MEDIUM/JA-2013-05051F_0027.GIF.
9. C. K. Winkler, J. H. Schrittwieser, and W. Kroutil, “Power of Biocatalysis for Organic Synthesis,” ACS Cent. Sci., vol. 7, no. 1, p. 55, Jan.
2021, doi: 10.1021/ACSCENTSCI.0C01496.
References
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19. THANK YOU!
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