bio catalysis

8/3/2019 Bio Catalysis

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Biocatalysis

From Wikipedia, the free encyclopediaBiocatalysis is the use of natural catalysts, such as proteinenzymes, to

perform chemical transformations on organic compounds. Both enzymes

that have been more or less isolated or enzymes still residing inside living

cells are employed for this task.[1][2][3]

Contents

[hide]

1 History

2 Advantages of

Biocatalysis

3 Asymmetric

biocatalysis

4 External links

5 References

[edit]History

Biocatalysis underpins some of the oldest chemical transformations known

to humans, forbrewing predates recorded history. The oldest records of

brewing are about 6000 years old and refer to the Sumerians.

The employment of enzymes and whole cells have been important for

many industries for centuries. The most obvious usages have been in the

food and drink businesses where the production of wine, beer, cheese etc.

is dependent on the effects of the microorganisms.

More than one hundred years ago, biocatalysis was employed to do

chemical transformations on non-natural man-made organic compounds,

and the last 30 years have seen a substantial increase in the application

of biocatalysis to produce fine chemicals, especially for thepharmaceutical

industry.

Since biocatalysis deals with enzymes and microorganisms, it is

historically clasified separately from "homogeneous catalysis" and

"heterogeneous catalysis". However, mechanistically speaking,

biocatalysis is simply a special case of heterogeneous catalysis.[4]

[edit]Advantages of Biocatalysis

The key word fororganic synthesis is selectivity which is necessary to

obtain a high yield of a specific product. There are a large range of

selective organic reactions available for most synthetic needs. However,

there is still one area where organic chemists are struggling, and that is

when chirality is involved, although considerable progress in chiral

synthesis has been achieved in recent years.
http://en.wikipedia.org/wiki/Catalystshttp://en.wikipedia.org/wiki/Catalystshttp://en.wikipedia.org/wiki/Enzymeshttp://en.wikipedia.org/wiki/Enzymeshttp://en.wikipedia.org/wiki/Organic_compoundshttp://tmp/svipl.tmp/javascript:toggleToc()http://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=1http://en.wikipedia.org/wiki/Brewinghttp://en.wikipedia.org/wiki/Sumerianshttp://en.wikipedia.org/wiki/Microorganismshttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Specialty_chemicalhttp://en.wikipedia.org/wiki/Pharmaceutical_industryhttp://en.wikipedia.org/wiki/Pharmaceutical_industryhttp://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=2http://en.wikipedia.org/wiki/Organic_synthesishttp://en.wikipedia.org/wiki/Chemoselectivityhttp://en.wikipedia.org/wiki/Organic_reactionhttp://en.wikipedia.org/wiki/Optical_isomerismhttp://en.wikipedia.org/wiki/Chiral_synthesishttp://en.wikipedia.org/wiki/Chiral_synthesishttp://en.wikipedia.org/wiki/Enzymeshttp://en.wikipedia.org/wiki/Organic_compoundshttp://tmp/svipl.tmp/javascript:toggleToc()http://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=1http://en.wikipedia.org/wiki/Brewinghttp://en.wikipedia.org/wiki/Sumerianshttp://en.wikipedia.org/wiki/Microorganismshttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Specialty_chemicalhttp://en.wikipedia.org/wiki/Pharmaceutical_industryhttp://en.wikipedia.org/wiki/Pharmaceutical_industryhttp://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=2http://en.wikipedia.org/wiki/Organic_synthesishttp://en.wikipedia.org/wiki/Chemoselectivityhttp://en.wikipedia.org/wiki/Organic_reactionhttp://en.wikipedia.org/wiki/Optical_isomerismhttp://en.wikipedia.org/wiki/Chiral_synthesishttp://en.wikipedia.org/wiki/Chiral_synthesishttp://en.wikipedia.org/wiki/Catalysts


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Enzymes display three major types of selectivities:

Chemoselectivity: Since the purpose of an enzyme is to act on a single

type of functional group, other sensitive functionalities, which would

normally react to a certain extent under chemical catalysis, survive. As

a result, biocatalytic reactions tend to be "cleaner" and laborious

purification of product(s) from impurities emerging through side-

reactions can largely be omitted.

Regioselectivity and Diastereoselectivity: Due to their complex three-

dimensional structure, enzymes may distinguish between functional

groups which are chemically situated in different regions of the

substrate molecule.

Enantioselectivity: Since almost all enzymes are made from L-amino

acids, enzymes are chiral catalysts. As a consequence, any type of

chirality present in the substrate molecule is "recognized" upon the

formation of the enzyme-substrate complex. Thus a prochiral substrate

may be transformed into an optically active product and both

enantiomers of a racemic substrate may react at different rates.

These reasons, and especially the latter, are the major reasons why

synthetic chemists have become interested in biocatalysis. This interest in

turn is mainly due to the need to synthesise enantiopure compounds as

chiral building blocks fordrugs and agrochemicals.

Another important advantage of biocatalysts are that they are

environmentally acceptable, being completely degraded in the

environment. Furthermore the enzymes act under mild conditions, which

minimizes problems of undesired side-reactions such as

decomposition,isomerization, racemizationand rearrangement, which

often plague traditional methodology.

[edit]Asymmetric biocatalysis

The use of biocatalysis to obtain enantiopure compounds can be divided

into two different methods;

1. Kinetic resolution of a racemic mixture

2. Biocatalysed asymmetric synthesis

In kinetic resolution of a racemic mixture, the presence of a chiral object

(the enzyme) converts one of the enantiomers into product at a

greaterreaction rate than the other enantiomer.
http://en.wikipedia.org/wiki/Chemoselectivityhttp://en.wikipedia.org/wiki/Regioselectivityhttp://en.wikipedia.org/wiki/Diastereoselectivityhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Enantioselectivityhttp://en.wikipedia.org/wiki/Amino_acidhttp://en.wikipedia.org/wiki/Amino_acidhttp://en.wikipedia.org/wiki/Enantiopurehttp://en.wikipedia.org/wiki/Medicationhttp://en.wikipedia.org/wiki/Agrochemicalhttp://en.wikipedia.org/wiki/Isomerizationhttp://en.wikipedia.org/wiki/Racemizationhttp://en.wikipedia.org/wiki/Racemizationhttp://en.wikipedia.org/wiki/Rearrangement_reactionhttp://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=3http://en.wikipedia.org/wiki/Kinetic_resolutionhttp://en.wikipedia.org/wiki/Reaction_ratehttp://en.wikipedia.org/wiki/Chemoselectivityhttp://en.wikipedia.org/wiki/Regioselectivityhttp://en.wikipedia.org/wiki/Diastereoselectivityhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Enantioselectivityhttp://en.wikipedia.org/wiki/Amino_acidhttp://en.wikipedia.org/wiki/Amino_acidhttp://en.wikipedia.org/wiki/Enantiopurehttp://en.wikipedia.org/wiki/Medicationhttp://en.wikipedia.org/wiki/Agrochemicalhttp://en.wikipedia.org/wiki/Isomerizationhttp://en.wikipedia.org/wiki/Racemizationhttp://en.wikipedia.org/wiki/Rearrangement_reactionhttp://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=3http://en.wikipedia.org/wiki/Kinetic_resolutionhttp://en.wikipedia.org/wiki/Reaction_rate


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The racemic mixture has now been transformed into a mixture of two

different compounds, making them separable by normal methodology. The

maximum yield in such kinetic resolutions is 50%, since a yield of more

than 50% means that some of wrong isomer also has reacted, giving a

lowerenantiomeric excess. Such reactions must therefore be terminated

before equilibrium is reached. If it is possible to perform such resolutions

under conditions where the two substrate- enantiomers are racemizing

continuously, all substrate may in theory be converted into enantiopure

product. This is called dynamic resolution.

In biocatalysed asymmetric synthesis, a non-chiral unit becomes chiral

in such a way that the different possible stereoismers are formed indifferent quantities. The chirality is introduced into the substrate by

influence of enzyme, which is chiral. Yeast is a biocatalyst for the

enantioselective reduction ofketones.

The biocatalytic Baeyer-Villiger oxidationis another example of abiocatalytic reaction. In one study a specially designed mutant ofCandida

Antarctica was found to be an effective catalyst for the Michael

addition ofacrolein with acetylacetone at 20C in absence of additional

solvent[5].

Another study demonstrates how racemic nicotine (mixture of S and R-

enantiomers 1 in scheme 3) can be deracemized in a one-pot procedure

involving a monoamine oxidase isolated from Aspergillus nigerwhich is

able to oxidize only the amineS-enantiomer to the imine2 and involvingan ammonia / boranereducing couple which can reduce the imine 2 back

to the amine 1[6]. In this way the S-enantiomer will continuously be

consumed by the enzyme while the R-enantiomer accumulates. It is even

possible to stereoinvert pure S to pure R.
http://en.wikipedia.org/wiki/Enantiomeric_excesshttp://en.wikipedia.org/wiki/Yeasthttp://en.wikipedia.org/wiki/Organic_reductionhttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Baeyer-Villiger_oxidationhttp://en.wikipedia.org/wiki/Baeyer-Villiger_oxidationhttp://en.wikipedia.org/wiki/Candida_(genus)http://en.wikipedia.org/wiki/Candida_(genus)http://en.wikipedia.org/wiki/Candida_(genus)http://en.wikipedia.org/wiki/Michael_additionhttp://en.wikipedia.org/wiki/Michael_additionhttp://en.wikipedia.org/wiki/Acroleinhttp://en.wikipedia.org/wiki/Acetylacetonehttp://en.wikipedia.org/wiki/%C2%B0Chttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/One-pot_synthesishttp://en.wikipedia.org/wiki/Aspergillus_nigerhttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Boranehttp://en.wikipedia.org/wiki/Reducing_agenthttp://en.wikipedia.org/wiki/Stereoinversionhttp://en.wikipedia.org/wiki/File:Yeastreduction.gifhttp://en.wikipedia.org/wiki/File:Kineticresolution.gifhttp://en.wikipedia.org/wiki/Enantiomeric_excesshttp://en.wikipedia.org/wiki/Yeasthttp://en.wikipedia.org/wiki/Organic_reductionhttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Baeyer-Villiger_oxidationhttp://en.wikipedia.org/wiki/Candida_(genus)http://en.wikipedia.org/wiki/Candida_(genus)http://en.wikipedia.org/wiki/Michael_additionhttp://en.wikipedia.org/wiki/Michael_additionhttp://en.wikipedia.org/wiki/Acroleinhttp://en.wikipedia.org/wiki/Acetylacetonehttp://en.wikipedia.org/wiki/%C2%B0Chttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/One-pot_synthesishttp://en.wikipedia.org/wiki/Aspergillus_nigerhttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Boranehttp://en.wikipedia.org/wiki/Reducing_agenthttp://en.wikipedia.org/wiki/Stereoinversion


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[edit]External links

The University of Exeter - Biocatalysis Centre

Applied Biocatalysis centre- Graz;

Center for Biocatalysis and Bioprocessing - The University of Iowa

TU Delft - Biocatalysis & Organic Chemistry (BOC)

KTH Stockholm - Biocatalysis Research Group

[edit]References

1. ^ Anthonsen, T. Reactions Catalyzed by Enzymes. InApplied Biocatalysis,

2. Ed. ; Adlercreutz. P.; #Straathof, A. J. J. Eds.; Harwood Academic

Publishers: UK,1999; pp 18-53

2. ^ Faber, K. Biotransformations in Organic Chemistry, 4th ed., Springer-

Verlag, Berlin 2000.

3. ^ Jayasinghe L. Y., Smallridge A. J., and Trewhella M. A. (1993). "The yeast

mediated reduction of ethyl acetoacetate in petroleum ether". Tetrahedron

Letters34(24): 3949. doi:10.1016/S0040-4039(00)79272-0.

4. ^ Gadi Rothenberg, Catalysis: Concepts and green applications, Wiley-VCH:

Weinheim, Feb. 2008, ISBN 978-3-527-31824-7.

5. ^ Maria Svedendahl, Karl Hult, and Per Berglund (2005). "Fast Carbon-

Carbon Bond Formation by a Promiscuous Lipase". J. Am. Chem.

Soc.127 (51): 1798817989.doi:10.1021/ja056660r.

6. ^ Colin J. Dunsmore, Reuben Carr, Toni Fleming, and Nicholas J. Turner

(2006). "A Chemo-Enzymatic Route to Enantiomerically Pure Cyclic Tertiary

Amines". J. Am. Chem. Soc.128 (7): 22242225. doi:10.1021/ja058536d.

[hide

]vde

Concepts inasymmetric synthesis

Chirality types Chirality StereocenterPlanar chiralityChiral ligandAxial chiralitySupramolecular chi

Chiral molecules StereoisomerEnantiomerDiastereomerMeso compoundEnantiomeric excess Diastere

Analysis Optical rotationChiral derivatizing agents NMR spectroscopy of stereoisomers Ultraviole

Chiral resolution Crystallization Kinetic resolution Chiral column chromatographyDiastereomeric recrysta
http://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=4http://centres.exeter.ac.uk/biocatalysis/http://www.a-b.tugraz.at/index_en.htmhttp://www.a-b.tugraz.at/index_en.htmhttp://www.uiowa.edu/~biocat/http://www.bt.tudelft.nl/bochttp://www.biotech.kth.se/biochem/biocatalysis/http://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=5http://en.wikipedia.org/wiki/Tetrahedron_Lettershttp://en.wikipedia.org/wiki/Tetrahedron_Lettershttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016/S0040-4039(00)79272-0http://en.wikipedia.org/wiki/Special:BookSources/9783527318247http://en.wikipedia.org/wiki/Special:BookSources/9783527318247http://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1021/ja056660rhttp://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1021/ja058536dhttp://tmp/svipl.tmp/javascript:collapseTable(0);http://en.wikipedia.org/wiki/Template:Chiral_synthesishttp://en.wikipedia.org/wiki/Template:Chiral_synthesishttp://en.wikipedia.org/w/index.php?title=Template_talk:Chiral_synthesis&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Template_talk:Chiral_synthesis&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Template:Chiral_synthesis&action=edithttp://en.wikipedia.org/w/index.php?title=Template:Chiral_synthesis&action=edithttp://en.wikipedia.org/wiki/Asymmetric_synthesishttp://en.wikipedia.org/wiki/Asymmetric_synthesishttp://en.wikipedia.org/wiki/Chirality_(chemistry)http://en.wikipedia.org/wiki/Stereocenterhttp://en.wikipedia.org/wiki/Stereocenterhttp://en.wikipedia.org/wiki/Planar_chiralityhttp://en.wikipedia.org/wiki/Planar_chiralityhttp://en.wikipedia.org/wiki/Chiral_ligandhttp://en.wikipedia.org/wiki/Chiral_ligandhttp://en.wikipedia.org/wiki/Chiral_ligandhttp://en.wikipedia.org/wiki/Axial_chiralityhttp://en.wikipedia.org/wiki/Axial_chiralityhttp://en.wikipedia.org/wiki/Axial_chiralityhttp://en.wikipedia.org/wiki/Supramolecular_chiralityhttp://en.wikipedia.org/wiki/Supramolecular_chiralityhttp://en.wikipedia.org/wiki/Stereoisomerismhttp://en.wikipedia.org/wiki/Enantiomerhttp://en.wikipedia.org/wiki/Diastereomerhttp://en.wikipedia.org/wiki/Diastereomerhttp://en.wikipedia.org/wiki/Meso_compoundhttp://en.wikipedia.org/wiki/Meso_compoundhttp://en.wikipedia.org/wiki/Enantiomeric_excesshttp://en.wikipedia.org/wiki/Enantiomeric_excesshttp://en.wikipedia.org/wiki/Diastereomeric_excesshttp://en.wikipedia.org/wiki/Optical_rotationhttp://en.wikipedia.org/wiki/Optical_rotationhttp://en.wikipedia.org/wiki/Chiral_derivatizing_agenthttp://en.wikipedia.org/wiki/Chiral_derivatizing_agenthttp://en.wikipedia.org/wiki/NMR_spectroscopy_of_stereoisomershttp://en.wikipedia.org/wiki/Ultraviolet-visible_spectroscopy_of_stereoisomershttp://en.wikipedia.org/wiki/Chiral_resolutionhttp://en.wikipedia.org/wiki/Crystallizationhttp://en.wikipedia.org/wiki/Kinetic_resolutionhttp://en.wikipedia.org/wiki/Chiral_column_chromatographyhttp://en.wikipedia.org/wiki/Chiral_column_chromatographyhttp://en.wikipedia.org/wiki/Chiral_column_chromatographyhttp://en.wikipedia.org/wiki/Diastereomeric_recrystallizationhttp://en.wikipedia.org/wiki/Diastereomeric_recrystallizationhttp://en.wikipedia.org/wiki/File:EnantiopuretertAmines.pnghttp://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=4http://centres.exeter.ac.uk/biocatalysis/http://www.a-b.tugraz.at/index_en.htmhttp://www.uiowa.edu/~biocat/http://www.bt.tudelft.nl/bochttp://www.biotech.kth.se/biochem/biocatalysis/http://en.wikipedia.org/w/index.php?title=Biocatalysis&action=edit&section=5http://en.wikipedia.org/wiki/Tetrahedron_Lettershttp://en.wikipedia.org/wiki/Tetrahedron_Lettershttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016/S0040-4039(00)79272-0http://en.wikipedia.org/wiki/Special:BookSources/9783527318247http://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1021/ja056660rhttp://en.wikipedia.org/wiki/J._Am._Chem._Soc.http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1021/ja058536dhttp://tmp/svipl.tmp/javascript:collapseTable(0);http://en.wikipedia.org/wiki/Template:Chiral_synthesishttp://en.wikipedia.org/w/index.php?title=Template_talk:Chiral_synthesis&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Template:Chiral_synthesis&action=edithttp://en.wikipedia.org/wiki/Asymmetric_synthesishttp://en.wikipedia.org/wiki/Chirality_(chemistry)http://en.wikipedia.org/wiki/Stereocenterhttp://en.wikipedia.org/wiki/Planar_chiralityhttp://en.wikipedia.org/wiki/Chiral_ligandhttp://en.wikipedia.org/wiki/Axial_chiralityhttp://en.wikipedia.org/wiki/Supramolecular_chiralityhttp://en.wikipedia.org/wiki/Stereoisomerismhttp://en.wikipedia.org/wiki/Enantiomerhttp://en.wikipedia.org/wiki/Diastereomerhttp://en.wikipedia.org/wiki/Meso_compoundhttp://en.wikipedia.org/wiki/Enantiomeric_excesshttp://en.wikipedia.org/wiki/Diastereomeric_excesshttp://en.wikipedia.org/wiki/Optical_rotationhttp://en.wikipedia.org/wiki/Chiral_derivatizing_agenthttp://en.wikipedia.org/wiki/NMR_spectroscopy_of_stereoisomershttp://en.wikipedia.org/wiki/Ultraviolet-visible_spectroscopy_of_stereoisomershttp://en.wikipedia.org/wiki/Chiral_resolutionhttp://en.wikipedia.org/wiki/Crystallizationhttp://en.wikipedia.org/wiki/Kinetic_resolutionhttp://en.wikipedia.org/wiki/Chiral_column_chromatographyhttp://en.wikipedia.org/wiki/Diastereomeric_recrystallization


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Reactions Asymmetric inductionChiral pool synthesis Chiral auxiliaries Asymmetric catalysisOrg

Categories: Enzymes | Organic chemistry | Catalysis

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