Biocatalysis Position In Green Chemistry · 2015-12-17 · Green Chemistry 1990 U.S. Environmental...
Transcript of Biocatalysis Position In Green Chemistry · 2015-12-17 · Green Chemistry 1990 U.S. Environmental...
Biocatalysis Position In Green Chemistry
How Green is Biocatalysis? To Calculate is To know Yan Ni, Dirk Holtmann and Frank Hollmann ChemcatChem 2014, 6, 930-945
http://www.nature.com/scitable/topicpage/cell-metabolism-14026182
DEFINITIONS AND CONCEPTS
+
A chemical reaction model:
Molecule 1 Molecule 2
= Molecule 3 Molecule 4
Organic synthesis concept
+ = Molecule 3
Molecule 6
Molecule 5
Organic synthesis is concerned with the construction of molecules, involving chemical reactions. Several reactions will take place one after another (or in parallel) until the targeted molecule is complete.
Molecule 3
Boot’s process for ibuprofen (analgesic like aspirin) synthesis
(1960) : 6 steps and numerous non
recyclable waste.
Example
Green Chemistry
1990 U.S. Environmental Protection Agency (EPA)
1998 12 principles of green chemistry by P. Anasta and J. Warner
Reduce the impact of chemistry on the environment by preventing pollution at its source and using fewer natural resources
Green chemistry efficiently utilizes (preferably renewable) raw materials, eliminates waste and avoids the use of toxic and/or hazardous reagents and solvents in the manufacture and application of chemical products.
2007 REACH European rules : to secure production and utilisation of chemicals
12 principles of Green Chemistry
Green Chemistry
Atom economy
Efficient production
Innocuous degradation
products
Preventing waste
Diminishing accidents
Save energy
Renewable feedstock
Real time measurement
Avoid derivatisations
Avoid auxiliary substances
Non-toxic substances
Catalysts
New process by BHC (1990): only 3 steps and only one sub-product (acetic acid) which is recycled for another use.
Example « Green process »
WILLSTÄTTER RICHARD - (1872-1942) Nobel price in 1915 chlorophyll and other plant pigments
"The vast number of chemical reactions taking part in a living cell are controlled by organic catalysts. Life is the orchestrated combination of processes catalyzed by enzymes."
Biocatalysis may be broadly defined as the use of enzymes or whole cells as biocatalysts for industrial or academic synthetic chemistry.
Biocatalysis
Enzyme ubiquity and diversity
Escherichia coli Human
~ 25000 genes ~ 20000 proteins ~ 15000 enzymes
4500 genes 1518 enzymes 1700 reactions
Nature, a molecule architect?
Eukaryotic cell Prokaryotic cell
Nature, a molecule architect?
Orchestration? Metabolic map…
Huge diversity of natural Compounds … and reactions
CHEMOSELECTIVITY, REGIOSELECTIVITY, STEREOSELECTIVITY
To give an idea: our Universe would contain 1080 atoms in the “eye accessible” part
An average protein would contain 300 aa and as 20 proteinogenic amino acids exist, 20300 (10390) different polymers are theoretically possible… The complete Universe is insufficient to contain a copy of each protein. An enzyme is thus able to bind a substrate specifically to lead to a chemical reaction.
Enzymes are chemoselective, regioselective and stereoselective
Chemoselectivity: reaction on a polyfunctional molecule possible without any protection. Regioselectivity: Identical functional groups distinguished depending on their position on the molecule. Stereoselectivity: enzymes are chiral catalysts. They are able to differentiate stereoisomers and in particular enantiomers.
How this can work?
From gene to protein
From gene to protein
Enzymes are proteins
Proteins are polymers (macromolecules) built up from amino acids.
Amino acids Dipeptide Oligopeptide
…
Protein
Organisation and folding of this chain lead to a 3D structure.
Enzymes are proteins
Cartoon representation
cristal
Soybean protein
They « cut » molecular assemblies into smaller molecules
They « stick » for constructing molecular assemblies
+ =
= +
Enzymes at work
Key and lock concept
Enzymes at work
http://biosciences.dupont.com/about-us/guide-to-industrial-enzymes/
http://culturesciences.chimie.ens.fr/dossiers-reactivite-catalyse-autresdocs-Enzymes_Laage_1.html#menu
http://www.classhelp.info/Biology/AUnit3Biochemistry.htm
Enzymes at work
http://science.halleyhosting.com/sci/ibbio/chem/notes/chpt8/chpt8.htm
http://www.nature.com/scitable/topicpage/protein-function-14123348
Rate factor increase from 107 to 1017 depending on the enzyme
Enzymes at work
http://www.geni.org/globalenergy/library/technical-articles/generation/future-fuels/iogen/enzyme-technology/index.shtml
How industrial enzymes are made? And in the lab?
Enzymes production
How enzymes are used?
However… Enzymes are denatured by a change in temperature, pH or chemical action
http://www.rsc.org/learn-chemistry/resources/chemistry-in-your-cupboard/vanish/8
In water, buffer, low temperature, mild conditions…
inactive
APPLICATIONS
Detergent, food, pharmaceutical, chemical and leather industries… are producing and/or using enzymes
https://chempics.wordpress.com/category/industrial-chemistry/
In food? Vanillin Industrial synthesis, artificial aroma
(From lignin)
.
Enzymes at home?
http://www.teknoscienze.com/Articles/HPC-Today-Detergent-enzymes-ndash-from-discovery-to-product-The-power-of.aspx#.U3eWhXJPHqM
Amylase
Cellulase
Protease
Microorganisms Tailored to the Raw Materials Available Ethanol is produced from non-food biomass such as farming and forest waste, green waste and dedicated crops. This involves extracting the cell wall (cellulosic) sugar from biomass utilizing enzymes that convert cellulose into sugar (glucose) through hydrolysis. Then yeast strains convert the sugars into ethanol via fermentation. The resultant ethanol is distilled to ensure it is of suitable quality for use as biofuel. For this biotechnology process to be profitable, more efficient enzymes are needed, which is a core focus of R&D in this area
http://total.com/en/energies-expertise/renewable-energies/biomass/projects-achievements/futurol
In cars? Bioethanol
CELL FACTORIES
http://www.nature.com/nchembio/journal/v8/n6/fig_tab/nchembio.970_F1.html
Categories of chemicals produced by cell factories
How to get efficient desired enzymes?
Efficient biocatalysts for fine green chemistry or
industrial chemistry
Biodiversity
De novo design (computer modelling) Directed evolution of
existing enzymes
Directed evolution
??
Desired biocatalyst
Wild-type biocatalyst
Directed evolution
NEW GENES => NEW ENZYMES WITH NEW PROPERTIES => SCREENING
Evolution Molecular biology
Screening
From biodivsersity
Harvest the DNA (genes) from the environment
Databases
Screening for the desired properties
New enzymes
http://www.uniprot.org http://www.rcsb.org/pdb/home/home.do http://biology.unm.edu/biology/maggieww/Public_Html/ANALYSIS.HTM (list of databases)
CONCLUSION
12 principles of Green Chemistry
Green Chemistry
Atom economy
Efficient production
Innocuous degradation
products
Preventing waste
Diminishing accidents
Save energy
Renewable feedstock
Real time measurement
Avoid derivatisations
Avoid auxiliary substances
Non-toxic substances
Catalysts
BIOCATALYSIS HAS A PRIVILEGED POSITION IN GREEN CHEMISTRY!