Biotransformation: Difference between revisions

Content deleted Content added

Inline

Latest revision as of 03:32, 1 February 2024

Biotransformation is the biochemical modification of one chemical compound or a mixture of chemical compounds. Biotransformations can be conducted with whole cells, their lysates, or purified enzymes.^[1] Increasingly, biotransformations are effected with purified enzymes. Major industries and life-saving technologies depend on biotransformations.^[2]^[3]

Advantages and disadvantages

Compared to the conventional production of chemicals, biotransformations are often attractive because their selectivities can be high, limiting the coproduction of undesirable coproducts. Generally operating under mild temperatures and pressures in aqueous solutions, many biotransformations are "green". The catalysts, i.e. the enzymes, are amenable to improvement by genetic manipulation.^{[citation needed]}

Biotechnology usually is restrained by substrate scope. Petrochemicals for example are often not amenable to biotransformations, especially on the scale required for some applications, e.g. fuels. Biotransformations can be slow and are often incompatible with high temperatures, which are employed in traditional chemical synthesis to increase rates. Enzymes are generally only stable <100 °C, and usually much lower. Enzymes, like other catalysts are poisonable. In some cases, performance or recyclability can be improved by using immobilized enzymes.^{[citation needed]}

Historical

Wine and beer making are examples of biotransformations that have been practiced since ancient times. Vinegar has long been produced by fermentation, involving the oxidation of ethanol to acetic acid. Cheesemaking traditionally relies on microbes to convert dairy precursors. Yogurt is produced by inoculating heat-treated milk with microorganisms such as Streptococcus thermophilus and Lactobacillus bulgaricus.^{[citation needed]}

Modern examples

Pharmaceuticals

Beta-lactam antibiotics, e.g., penicillin and cephalosporin are produced by biotransformations in an industry valued several billions of dollars. Processes are conducted in vessels up to 60,000 gal in volume. Sugars, methionine, and ammonium salts are used as C,S,N sources. Genetically modified Penicillium chrysogenum is employed for penicillin production.^[4]

Some steroids are hydroxylated in vitro to give drugs.

Sugars

High fructose corn syrup is generated by biotransformation of corn starch, which is converted to a mixture of glucose and fructose. Glucoamylase is one enzyme used in the process.^[5]

Cyclodextrins are produced by transferases.

Amino acids

Amino acids are sometimes produced industrially by transaminases. In other cases, amino acids are obtained by biotransformations of peptides using peptidases.^{[citation needed]}

Acrylamide

With acrylonitrile and water as substrates, nitrile hydratase enzymes are used to produce acrylamide, a valued monomer.^{[citation needed]}

Biofuels

Many kinds of fuels and lubricants are produced by processes that include biotransformations starting from natural precursors such as fats, cellulose, and sugars.^{[citation needed]}

References

^ "Biotransformation". IUPAC Goldbook. 2014. doi:10.1351/goldbook.B00667. Retrieved 14 February 2022.
^ Andreas Liese; Karsten Seelbach; Christian Wandrey (2006). Liese, Andreas; Seelbach, Karsten; Wandrey, Christian (eds.). Industrial biotransformations (2 ed.). Weinheim: Wiley-VCH. doi:10.1002/3527608184. ISBN 978-3-527-31001-2.
^ Kamm, Birgit; Gruber, Patrick R.; Kamm, Michael (2016). "Biorefineries-Industrial Processes and Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–38. doi:10.1002/14356007.l04_l01.pub2. ISBN 978-3-527-30673-2.
^ Elander, R. P. (2003). "Industrial production of β-lactam antibiotics". Applied Microbiology and Biotechnology. 61 (5–6): 385–392. doi:10.1007/s00253-003-1274-y. PMID 12679848. S2CID 43996071.
^ Hobbs, Larry (2009). "21. Sweeteners from Starch: Production, Properties and Uses". In BeMiller, James N.; Whistler, Roy L. (eds.). Starch: chemistry and technology (3rd ed.). London: Academic Press/Elsevier. pp. 797–832. doi:10.1016/B978-0-12-746275-2.00021-5. ISBN 978-0-12-746275-2.

[1] "Biotransformation". IUPAC Goldbook. 2014. doi:10.1351/goldbook.B00667. Retrieved 14 February 2022.

[2] Andreas Liese; Karsten Seelbach; Christian Wandrey (2006). Liese, Andreas; Seelbach, Karsten; Wandrey, Christian (eds.). Industrial biotransformations (2 ed.). Weinheim: Wiley-VCH. doi:10.1002/3527608184. ISBN 978-3-527-31001-2.

[3] Kamm, Birgit; Gruber, Patrick R.; Kamm, Michael (2016). "Biorefineries-Industrial Processes and Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–38. doi:10.1002/14356007.l04_l01.pub2. ISBN 978-3-527-30673-2.

[4] Elander, R. P. (2003). "Industrial production of β-lactam antibiotics". Applied Microbiology and Biotechnology. 61 (5–6): 385–392. doi:10.1007/s00253-003-1274-y. PMID 12679848. S2CID 43996071.

[Hobbs-5] Hobbs, Larry (2009). "21. Sweeteners from Starch: Production, Properties and Uses". In BeMiller, James N.; Whistler, Roy L. (eds.). Starch: chemistry and technology (3rd ed.). London: Academic Press/Elsevier. pp. 797–832. doi:10.1016/B978-0-12-746275-2.00021-5. ISBN 978-0-12-746275-2.

[1]

[2]

[3]

[4]

[5]

@@ Line 1: / Line 1: @@
+{{Short description|Chemical alteration of an exogenous substance by or in a biological system}}
-'''Biotransformation''' is the chemical modification (or modifications) made by an organism on a chemical compound. If this modification ends in mineral compounds like [[carbon dioxide|CO<sub>2</sub>]], [[ammonium|NH<sub>4</sub><sup>+</sup>]], or [[water|H<sub>2</sub>O]], the biotransformation is called [[Mineralization (biology)|mineralisation]].
+'''Biotransformation''' is the biochemical modification of one chemical compound or a mixture of chemical compounds. Biotransformations can be conducted with whole cells, their lysates, or purified enzymes.<ref>{{cite journal |title=Biotransformation |url=https://goldbook.iupac.org/terms/view/B00667 |website=IUPAC Goldbook |year=2014 |doi=10.1351/goldbook.B00667 |access-date=14 February 2022|doi-access=free }}</ref>  Increasingly, biotransformations are effected with purified [[enzyme]]s.  Major industries and life-saving technologies depend on biotransformations.<ref>{{cite book|title=Industrial biotransformations |author=Andreas Liese |author2=Karsten Seelbach |author3=Christian Wandrey|editor1-first=Andreas|editor1-last=Liese|editor2-first=Karsten|editor2-last=Seelbach|editor3-first=Christian|editor3-last=Wandrey|edition=2|publisher=Wiley-VCH|location=Weinheim|year=2006|isbn= 978-3-527-31001-2 |doi=10.1002/3527608184}}</ref><ref>{{Ullmann|doi=10.1002/14356007.l04_l01.pub2|title=Biorefineries-Industrial Processes and Products|year=2016|last1=Kamm|first1=Birgit|last2=Gruber|first2=Patrick R.|last3=Kamm|first3=Michael|pages=1–38|isbn=978-3-527-30673-2}}</ref>
+==Advantages and disadvantages==
-Biotransformation means chemical alteration of chemicals such as [[nutrient]]s, [[amino acids]], [[toxins]], and drugs in the body. It is also needed to render non-[[Chemical polarity|polar compounds]] to polar compounds. so that they are not reabsorbed in renal tubules and are excreted. Biotransformation of xenobiotics can dominate [[toxicokinetics]] and the metabolites may reach higher concentrations in organisms than their parent compounds.<ref>{{cite journal | last1 = Ashauer | first1 = R | last2 = Hintermeister | first2 = A | last3 = O'Connor | first3 = I | last4 = Elumelu | first4 = M |display-authors=et al | year = 2012 | title = Significance of Xenobiotic Metabolism for Bioaccumulation Kinetics of Organic Chemicals in Gammarus pulex | doi = 10.1021/es204611h | pmid = 22321051 | pmc = 3308200 | journal = Environ. Sci. Technol. | volume =  46| issue = 6| pages =  3498–3508}}</ref> Recently its application is seen as an efficient, cost effective, and easily applicable approach for the valorization of agricultural wastes with potentials of enhancing existing bioactive components and synthesis of new compounds.<ref>{{cite journal |last1=Uchenna |first1=Amadi |last2=Uchechi |first2=Ogunka-Nnoka |last3=Bene |first3=Abbey |title=Properties of oils from plantain pseudostem biotransformed using crude local enzyme sources: a comparison of poultry feed oil |journal=Recent Pat Food Nutr Agric |date=2018 |volume=10 |doi=10.2174/2212798410666181217141311 |pmid=30556509}}</ref><ref>{{cite journal |last1=Amadi |first1=Peter |last2=Ogunka-Nnoka |first2=Charity |last3=Bene |first3=Abbey |title=Biotransformation of plantain pseudostem fibres using local enzyme sources; analysis of their potential as commercial poultry feed |journal=Biocatalysis and Biotransformation |volume=36 |pages=1–9 |doi=10.1080/10242422.2018.1532412 |year=2018 }}</ref>
+Compared to the conventional production of chemicals, biotransformations are often attractive because their selectivities can be high, limiting the coproduction of undesirable coproducts. Generally operating under mild temperatures and pressures in aqueous solutions, many biotransformations are [[green chemistry|"green"]]. The catalysts, i.e. the enzymes, are amenable to improvement by genetic manipulation.{{citation needed|date=February 2024}}
+Biotechnology usually is restrained by substrate scope. Petrochemicals for example are often not amenable to biotransformations, especially on the scale required for some applications, e.g. fuels. Biotransformations can be slow and are often incompatible with high temperatures, which are employed in traditional chemical synthesis to increase rates. Enzymes are generally only stable <100&nbsp;°C, and usually much lower. Enzymes, like other catalysts are poisonable. In some cases, performance or recyclability can be improved by using [[immobilized enzyme]]s.{{citation needed|date=February 2024}}
-==Drug metabolism==
-{{Main|Drug metabolism}}
-The metabolism of a [[drug]] or toxin in a body is an example of a biotransformation. The body typically deals with a foreign compound by making it more water-soluble, to increase the rate of its excretion through the urine. There are many different processes that can occur; the pathways of drug metabolism can be divided into:
-* phase І
-* phase II
-Drugs can undergo one of four potential biotransformations: Active Drug to Inactive Metabolite, Active Drug to Active Metabolite, Inactive Drug to Active Metabolite, Active Drug to Toxic Metabolite (biotoxification).
+==Historical==
-===Phase І reaction===
+Wine and beer making are examples of biotransformations that have been practiced since ancient times.  Vinegar has long been produced by fermentation, involving the oxidation of ethanol to [[acetic acid]].  [[Cheesemaking]] traditionally relies on microbes to convert dairy precursors.  [[Yogurt]] is produced by inoculating heat-treated milk with microorganisms such as ''[[Streptococcus thermophilus]]'' and ''[[Lactobacillus bulgaricus]]''.{{citation needed|date=February 2024}}
-* Includes oxidative, reductive, and [[hydrolytic]] reactions.
-* In these types of reactions, a polar group is either introduced or unmasked, so the [[Small molecule|drug molecule]] becomes more water-soluble and can be excreted.
-* Reactions are non-synthetic in nature and in general produce a more water-soluble and less active metabolites.
-* The majority of metabolites are generated by a common [[hydroxylating]] enzyme system known as [[Cytochrome P450]].
-===Phase II reaction===
+==Modern examples==
+===Pharmaceuticals===
-* These reactions involve covalent attachment of small [[hydrophilic]] endogenous molecule such as [[glucuronic acid]], [[sulfate]], or [[glycine]] to form water-soluble compounds, that are more hydrophilic.
+[[Beta-lactam antibiotic]]s, e.g., [[penicillin]] and [[cephalosporin]] are produced by biotransformations in an industry valued several billions of dollars.  Processes are conducted in vessels up to 60,000 gal in volume.  Sugars, methionine, and ammonium salts are used as C,S,N sources.  Genetically modified ''Penicillium chrysogenum'' is employed for penicillin production.<ref>{{Cite journal
-* This is also known as a conjugation reaction.
+ | last1 = Elander | first1 = R. P.
-* The final compounds have a larger molecular weight.
+ | title = Industrial production of β-lactam antibiotics
+ | journal = Applied Microbiology and Biotechnology
+ | volume = 61
+ | issue = 5–6
+ | pages = 385–392
+ | doi = 10.1007/s00253-003-1274-y
+ | year = 2003
+ | pmid = 12679848
+| s2cid = 43996071
+ }}</ref>
+Some [[steroid]]s are [[hydroxylate]]d ''in vitro'' to give drugs.
-==Microbial biotransformation==
-Biotransformation of various [[pollutant]]s is a sustainable way to clean up contaminated environments.<ref name=Diaz>{{cite book | author = Diaz E (editor). | title = Microbial Biodegradation: Genomics and Molecular Biology | edition = 1st | publisher = Caister Academic Press | year = 2008 | url = https://archive.org/details/microbialbiodegr0000unse | isbn = 978-1-904455-17-2 | url-access = registration }}</ref> These [[bioremediation]] and biotransformation methods harness the naturally occurring, microbial catabolic diversity to degrade, transform or accumulate a huge range of compounds including [[hydrocarbon]]s (e.g. oil), [[polychlorinated biphenyls]] (PCBs), [[polyaromatic hydrocarbons]] (PAHs), pharmaceutical substances, [[radionuclide]]s and metals. Major methodological breakthroughs in recent years have enabled detailed genomic, metagenomic, proteomic, bioinformatic and other high-throughput analyses of environmentally relevant [[microorganism]]s providing unprecedented insights into biotransformation and [[microbial biodegradation|biodegradative]] pathways and the ability of organisms to adapt to changing environmental conditions.
+===Sugars===
-Biological processes play a major role in the removal of [[contaminant]]s and [[pollutant]]s from the [[Natural environment|environment]]. Some microorganisms possess an astonishing catabolic versatility to degrade or transform such compounds. New methodological breakthroughs in [[sequencing]], [[genomics]], [[proteomics]], [[bioinformatics]] and imaging are producing vast amounts of information. In the field of Environmental [[Microbiology]], [[genome]]-based global studies open a new era providing unprecedented ''in silico'' views of metabolic and regulatory networks, as well as clues to the evolution of biochemical pathways relevant to biotransformation and to the molecular adaptation strategies to changing environmental conditions. Functional genomic and metagenomic approaches are increasing our understanding of the relative importance of different pathways and regulatory networks to carbon flux in particular environments and for particular compounds and they are accelerating the development of [[bioremediation]] technologies and biotransformation processes.<ref name="Diaz"/>
+[[High fructose corn syrup]] is generated by biotransformation of [[corn starch]], which is converted to a mixture of [[glucose]] and [[fructose]]. [[Glucoamylase]] is one enzyme used in the process.<ref name=Hobbs>{{cite book|last1=Hobbs|first1=Larry|editor1-last=BeMiller|editor1-first=James N.|editor2-last=Whistler|editor2-first=Roy L.|title=Starch: chemistry and technology|date=2009|publisher=Academic Press/Elsevier|location=London|isbn=978-0-12-746275-2|pages=797–832|edition=3rd|doi=10.1016/B978-0-12-746275-2.00021-5|chapter=21. Sweeteners from Starch: Production, Properties and Uses}}</ref>
-Also there is other approach of biotransformation called enzymatic biotransformation.
+[[Cyclodextrin]]s are produced by [[transferase]]s.
-==Oil biodegradation==
-[[Petroleum]] oil is toxic for most life forms and episodic and chronic [[pollution]] of the environment by oil causes major ecological perturbations. Marine environments are especially vulnerable, since oil spills of coastal regions and the open sea are poorly containable and mitigation is difficult. In addition to pollution through human activities, millions of tons of petroleum enter the marine environment every year from natural seepages. Despite its toxicity, a considerable fraction of petroleum oil entering marine systems is eliminated by the hydrocarbon-degrading activities of microbial communities, in particular by a remarkable recently discovered group of specialists, the so-called [[hydrocarbonoclastic bacteria]] (HCB). ''[[Alcanivorax borkumensis]]'', a paradigm of HCB and probably the most important global oil degrader, was the first to be subjected to a functional genomic analysis. This analysis has yielded important new insights into its capacity for (i) n-alkane degradation including metabolism, [[biosurfactant]] production and [[biofilm]] formation, (ii) scavenging of nutrients and cofactors in the oligotrophic marine environment, as well as (iii) coping with various habitat-specific stresses. The understanding thereby gained constitutes a significant advance in efforts towards the design of new knowledge-based strategies for the mitigation of ecological damage caused by oil pollution of marine habitats. HCB also have potential biotechnological applications in the areas of [[bioplastic]]s and [[biocatalysis]].<ref name=chapter9>{{cite book|chapterurl=http://www.horizonpress.com/biod|author=Martins VAP|year=2008|chapter=Genomic Insights into Oil Biodegradation in Marine Systems|title=Microbial Biodegradation: Genomics and Molecular Biology|publisher=Caister Academic Press|isbn=978-1-904455-17-2|display-authors=etal|url-access=registration|url=https://archive.org/details/microbialbiodegr0000unse}}</ref>
+===Amino acids===
-==Metabolic engineering and biocatalytic applications==
+[[Amino acid]]s are sometimes produced industrially by [[transaminase]]s.  In other cases, amino acids are obtained by biotransformations of peptides using [[peptidase]]s.{{citation needed|date=February 2024}}
-The study of the fate of persistent organic chemicals in the environment has revealed a large reservoir of enzymatic reactions with a large potential in preparative organic synthesis, which has already been exploited for a number of [[oxygenase]]s on pilot and even on industrial scale. Novel catalysts can be obtained from [[metagenomic]] libraries and [[DNA sequence]] based approaches. Our increasing capabilities in adapting the catalysts to specific reactions and process requirements by rational and random [[mutagenesis]] broadens the scope for application in the fine chemical industry, but also in the field of [[biodegradation]]. In many cases, these catalysts need to be exploited in whole cell [[bioconversion]]s or in [[fermentation (biochemistry)|fermentation]]s, calling for system-wide approaches to understanding strain physiology and metabolism and rational approaches to the engineering of whole cells as they are increasingly put forward in the area of systems [[biotechnology]] and [[synthetic biology]].<ref name=chapter12>{{cite book|chapterurl=http://www.horizonpress.com/biod|author=Meyer A and Panke S|year=2008|chapter=Genomics in Metabolic Engineering and Biocatalytic Applications of the Pollutant Degradation Machinery|title=Microbial Biodegradation: Genomics and Molecular Biology|publisher=Caister Academic Press|isbn=978-1-904455-17-2|url-access=registration|url=https://archive.org/details/microbialbiodegr0000unse}}</ref>
+===Acrylamide===
+With [[acrylonitrile]] and water as substrates, [[nitrile hydratase]] enzymes are used to produce [[acrylamide]], a valued [[monomer]].{{citation needed|date=February 2024}}
+===Biofuels===
+{{main|biofuel}}
+Many kinds of fuels and [[lubricant]]s are produced by processes that include biotransformations starting from natural precursors such as [[fat]]s, [[cellulose]], and [[sugar]]s.{{citation needed|date=February 2024}}
 ==See also==
+* [[Biotechnology]]
 * [[Biodegradation]]
-* [[Microbial biodegradation]]
-* [[Xenobiotic metabolism]]
 ==References==
-{{reflist|30em}}
+{{reflist}}
+{{Authority control}}
-== External links ==
-* [http://www.pharmatutor.org/pharmacology/general-pharmacology/metabolism.html Biotransformation of Drugs]
-* [http://www.horizonpress.com/gateway/biodegradation.html Biodegradation, Bioremediation and Biotransformation]
-* [https://web.archive.org/web/20071011061623/http://horizonpress.com/blogger/2007/09/microbial-biodegradation-bioremediation.html Microbial Biodegradation]
-* [http://www.ecotoxmodels.org/research-publications-projects/bioaccumulation-biotransformation Biotransformation and Bioaccumulation in freshwater invertebrates]
-* [http://www.ecotoxmodels.org Ecotoxicology & Models]
 [[Category:Bioremediation]]