Insights into the unique carboxylation reactions in the metabolism of propylene and acetone

Mus, Florence; Wu, Hsin-Hua; Alleman, Alexander B.; Shisler, Krista A.; Zadvornyy, Oleg A.; Bothner, Brian; Dubois, Jennifer L.; Peters, John W.

doi:10.1042/bcj20200174

Insights into the unique carboxylation reactions in the metabolism of propylene and acetone

Journal Article · Thu Jun 04 00:00:00 EDT 2020 · Biochemical Journal

DOI:https://doi.org/10.1042/bcj20200174· OSTI ID:1804018

^[1]; Wu, Hsin-Hua ^[2]; Alleman, Alexander B. ^[3]; Shisler, Krista A. ^[3]; Zadvornyy, Oleg A. ^[3]; Bothner, Brian ^[4]; Dubois, Jennifer L. ^[4]; ^[3]

Institute of Biological Chemistry, Washington State University, Pullman, WA 99164, U.S.A.; OSTI
Institute of Biological Chemistry, Washington State University, Pullman, WA 99164, U.S.A.; Department of Chemistry, Washington State University, WA 99164
Institute of Biological Chemistry, Washington State University, Pullman, WA 99164, U.S.A.
Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, U.S.A.

Alkenes and ketones are two classes of ubiquitous, toxic organic compounds in natural environments produced in several biological and anthropogenic processes. In spite of their toxicity, these compounds are utilized as primary carbon and energy sources or are generated as intermediate metabolites in the metabolism of other compounds by many diverse bacteria. The aerobic metabolism of some of the smallest and most volatile of these compounds (propylene, acetone, isopropanol) involves novel carboxylation reactions resulting in a common product acetoacetate. Propylene is metabolized in a four-step pathway involving five enzymes where the penultimate step is a carboxylation reaction catalyzed by a unique disulfide oxidoreductase that couples reductive cleavage of a thioether linkage with carboxylation to produce acetoacetate. The carboxylation of isopropanol begins with conversion to acetone via an alcohol dehydrogenase. Acetone is converted to acetoacetate in a single step by an acetone carboxylase which couples the hydrolysis of MgATP to the activation of both acetone and bicarbonate, generating highly reactive intermediates that are condensed into acetoacetate at a Mn2+ containing the active site. Acetoacetate is then utilized in central metabolism where it is readily converted to acetyl-coenzyme A and subsequently converted into biomass or utilized in energy metabolism via the tricarboxylic acid cycle. This review summarizes recent structural and biochemical findings that have contributed significant insights into the mechanism of these two unique carboxylating enzymes.

Research Organization:: Montana State Univ., Bozeman, MT (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: FG02-04ER15563

OSTI ID:: 1804018

Journal Information:: Biochemical Journal, Journal Name: Biochemical Journal Journal Issue: 11 Vol. 477; ISSN 0264-6021

Publisher:: Biochemical Society

Country of Publication:: United States

Language:: English

References (85)

Modular Synthase-Encoding Gene Involved in α-Olefin Biosynthesis in Synechococcus sp. Strain PCC 7002 Mendez-Perez, Daniel; Begemann, Matthew B.; Pfleger, Brian F. Applied and Environmental Microbiology, Vol. 77, Issue 12, p. 4264-4267 https://doi.org/10.1128/AEM.00467-11	journal	April 2011
A novel type of pyridine nucleotide-disulfide oxidoreductase is essential for NAD+- and NADPH-dependent degradation of epoxyalkanes by Xanthobacter strain Py2. Swaving, J.; de Bont, J. A.; Westphal, A. Journal of Bacteriology, Vol. 178, Issue 22 https://doi.org/10.1128/JB.178.22.6644-6646.1996	journal	November 1996
Purification and characterization of a flavoprotein involved in the degradation of epoxyalkanes by Xanthobacter Py2 Westphal, Adrie H.; Swaving, Jelto; Jacobs, Linda European Journal of Biochemistry, Vol. 257, Issue 1 https://doi.org/10.1046/j.1432-1327.1998.2570160.x	journal	October 1998
Carbon dioxide fixation in the metabolism of propylene and propylene oxide by Xanthobacter strain Py2. Small, F. J.; Ensign, S. A. Journal of Bacteriology, Vol. 177, Issue 21 https://doi.org/10.1128/jb.177.21.6170-6175.1995	journal	November 1995
Assessing the Substrate Selectivities and Enantioselectivities of Eight Novel Baeyer−Villiger Monooxygenases toward Alkyl-Substituted Cyclohexanones Kyte, Brian G.; Rouvière, Pierre; Cheng, Qiong The Journal of Organic Chemistry, Vol. 69, Issue 1 https://doi.org/10.1021/jo030253l	journal	December 2003
Acetone and Butanone Metabolism of the Denitrifying Bacterium "Aromatoleum aromaticum" Demonstrates Novel Biochemical Properties of an ATP-Dependent Aliphatic Ketone Carboxylase Schuhle, K.; Heider, J. Journal of Bacteriology, Vol. 194, Issue 1 https://doi.org/10.1128/JB.05895-11	journal	October 2011
The β-Ketoadipate Pathway And The Biology Of Self-Identity Harwood, Caroline S.; Parales, Rebecca E. Annual Review of Microbiology, Vol. 50, Issue 1, p. 553-590 https://doi.org/10.1146/annurev.micro.50.1.553	journal	October 1996
Carbon dioxide fixation in the metabolism of propylene and propylene oxide by Xanthobacter strain Py2. Small, F. J.; Ensign, S. A. Journal of Bacteriology, Vol. 177, Issue 21 https://doi.org/10.1128/JB.177.21.6170-6175.1995	journal	November 1995
Crystal Structures of Nitroalkane Oxidase: Insights into the Reaction Mechanism from a Covalent Complex of the Flavoenzyme Trapped during Turnover Nagpal, Akanksha; Valley, Michael P.; Fitzpatrick, Paul F. Biochemistry, Vol. 45, Issue 4 https://doi.org/10.1021/bi051966w	journal	January 2006
Contribution of cyanobacterial alkane production to the ocean hydrocarbon cycle Lea-Smith, David J.; Biller, Steven J.; Davey, Matthew P. Proceedings of the National Academy of Sciences, Vol. 112, Issue 44 https://doi.org/10.1073/pnas.1507274112	journal	October 2015
Coenzyme M biosynthesis in bacteria involves phosphate elimination by a functionally distinct member of the aspartase/fumarase superfamily Partovi, Sarah E.; Mus, Florence; Gutknecht, Andrew E. Journal of Biological Chemistry, Vol. 293, Issue 14 https://doi.org/10.1074/jbc.RA117.001234	journal	April 2018
Characterization and genomic analysis of kraft lignin biodegradation by the beta-proteobacterium Cupriavidus basilensis B-8 Shi, Yan; Chai, Liyuan; Tang, Chongjian Biotechnology for Biofuels, Vol. 6, Issue 1 https://doi.org/10.1186/1754-6834-6-1	journal	January 2013
Divergent Metabolic Pathways for Propane and Propionate Utilization by a Soil Isolate Vestal, J. R.; Perry, Jerome J. Journal of Bacteriology, Vol. 99, Issue 1 https://doi.org/10.1128/JB.99.1.216-221.1969	journal	July 1969
Ror2 signaling regulates Golgi structure and transport through IFT20 for tumor invasiveness Nishita, Michiru; Park, Seung-Yeol; Nishio, Tadashi Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/s41598-016-0028-x	journal	January 2017
Toxicity of Benzene, Toluene, Ethylbenzene, and Xylene (BTEX) Mixtures to Sorghum bicolor and Cucumis sativus An, Y. -J. Bulletin of Environmental Contamination and Toxicology, Vol. 72, Issue 5 https://doi.org/10.1007/s00128-004-0343-y	journal	May 2004
Microbial Biosynthesis of Alkanes Schirmer, A.; Rude, M. A.; Li, X. Science, Vol. 329, Issue 5991, p. 559-562 https://doi.org/10.1126/science.1187936	journal	July 2010
Characterization of Five Catalytic Activities Associated with the NADPH:2-Ketopropyl-coenzyme M [2-(2-Ketopropylthio)ethanesulfonate] Oxidoreductase/Carboxylase of the Xanthobacter Strain Py2 Epoxide Carboxylase System ^† Clark, Daniel D.; Allen, Jeffrey R.; Ensign, Scott A. Biochemistry, Vol. 39, Issue 6 https://doi.org/10.1021/bi992282p	journal	February 2000
Structural Basis for CO ₂ Fixation by a Novel Member of the Disulfide Oxidoreductase Family of Enzymes, 2-Ketopropyl-Coenzyme M Oxidoreductase/Carboxylase ^† ^, ^‡ Nocek, Boguslaw; Jang, Se Bok; Jeong, Mi Suk Biochemistry, Vol. 41, Issue 43 https://doi.org/10.1021/bi026580p	journal	October 2002
Microbial Metabolism of Aliphatic Alkenes ^† Ensign, Scott A. Biochemistry, Vol. 40, Issue 20 https://doi.org/10.1021/bi015523d	journal	May 2001
Characterization of Cyanobacterial Hydrocarbon Composition and Distribution of Biosynthetic Pathways Coates, R. Cameron; Podell, Sheila; Korobeynikov, Anton PLoS ONE, Vol. 9, Issue 1 https://doi.org/10.1371/journal.pone.0085140	journal	January 2014
The reactive form of a C–S bond–cleaving, CO2-fixing flavoenzyme Streit, Bennett R.; Mattice, Jenna R.; Prussia, Gregory A. Journal of Biological Chemistry, Vol. 294, Issue 13 https://doi.org/10.1074/jbc.RA118.005554	journal	March 2019
Anaerobic degradation of toluene and o-xylene by a methanogenic consortium. Edwards, E. A.; Grbić-Galić, D. Applied and Environmental Microbiology, Vol. 60, Issue 1 https://doi.org/10.1128/AEM.60.1.313-322.1994	journal	January 1994
Metabolism of Methylglyoxal in Microorganisms Cooper, R. A. Annual Review of Microbiology, Vol. 38, Issue 1 https://doi.org/10.1146/annurev.mi.38.100184.000405	journal	October 1984
Acetol monooxygenase from Mycobacterium Py1 cleaves acetol into acetate and formaldehyde Hartmans, Sybe; Bont, Jan A. M. FEMS Microbiology Letters, Vol. 36, Issue 2-3 https://doi.org/10.1111/j.1574-6968.1986.tb01686.x	journal	September 1986
New Insights into Acetone Metabolism Hausinger, R. P. Journal of Bacteriology, Vol. 189, Issue 3 https://doi.org/10.1128/JB.01578-06	journal	December 2006
Involvement of an ATP-dependent carboxylase in a CO2-dependent pathway of acetone metabolism by Xanthobacter strain Py2. Sluis, M. K.; Small, F. J.; Allen, J. R. Journal of bacteriology, Vol. 178, Issue 14 https://doi.org/10.1128/JB.178.14.4020-4026.1996	journal	January 1996
Evidence for Only Oxygenative Cleavage of Aldehydes to Alk(a/e)nes and Formate by Cyanobacterial Aldehyde Decarbonylases Li, Ning; Chang, Wei-chen; Warui, Douglas M. Biochemistry, Vol. 51, Issue 40 https://doi.org/10.1021/bi300912n	journal	September 2012
Novel Acetone Metabolism in a Propane-Utilizing Bacterium, Gordonia sp. Strain TY-5 Kotani, T.; Yurimoto, H.; Kato, N. Journal of Bacteriology, Vol. 189, Issue 3 https://doi.org/10.1128/JB.01054-06	journal	October 2006
Has acetone a role in the conversion of fat to carbohydrate in mammals? Argilés, Josep M. Trends in Biochemical Sciences, Vol. 11, Issue 2 https://doi.org/10.1016/0968-0004(86)90256-2	journal	February 1986
Substitution of a conserved catalytic dyad into 2-KPCC causes loss of carboxylation activity Prussia, Gregory A.; Gauss, George H.; Mus, Florence FEBS Letters, Vol. 590, Issue 17 https://doi.org/10.1002/1873-3468.12325	journal	August 2016
Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803 ^T Grossi, Vincent; Cravo-Laureau, Cristiana; Méou, Alain Applied and Environmental Microbiology, Vol. 73, Issue 24 https://doi.org/10.1128/AEM.01097-07	journal	December 2007
Identification and Characterization of Epoxide Carboxylase Activity in Cell Extracts of Nocardia corallina B276 Allen, Jeffrey R.; Ensign, Scott A. Journal of Bacteriology, Vol. 180, Issue 8 https://doi.org/10.1128/JB.180.8.2072-2078.1998	journal	April 1998
Oxidation of Gaseous and Volatile Hydrocarbons by Selected Alkene-Utilizing Bacteria van Ginkel, C. G.; Welten, H. G. J.; de Bont, J. A. M. Applied and Environmental Microbiology, Vol. 53, Issue 12 https://doi.org/10.1128/AEM.53.12.2903-2907.1987	journal	January 1987
Roles of the Redox-Active Disulfide and Histidine Residues Forming a Catalytic Dyad in Reactions Catalyzed by 2-Ketopropyl Coenzyme M Oxidoreductase/Carboxylase Kofoed, M. A.; Wampler, D. A.; Pandey, A. S. Journal of Bacteriology, Vol. 193, Issue 18 https://doi.org/10.1128/JB.05231-11	journal	July 2011
Structure and Methylation of Coenzyme M (HSCH2CH2SO3) Taylor, Craig D.; Wolfe, Ralph S. Journal of Biological Chemistry, Vol. 249, Issue 15 https://doi.org/10.1016/S0021-9258(19)42403-4	journal	August 1974
Proton Sharing between Cysteine Thiols in Escherichia coli Thioredoxin: Implications for the Mechanism of Protein Disulfide Reduction Jeng, Mei-Fen; Holmgren, Arne; Dyson, H. Jane Biochemistry, Vol. 34, Issue 32 https://doi.org/10.1021/bi00032a001	journal	August 1995
Characterization of a new pathway for epichlorohydrin degradation by whole cells of xanthobacter strain py2. Small, F. J.; Tilley, J. K.; Ensign, S. A. Applied and environmental microbiology, Vol. 61, Issue 4 https://doi.org/10.1128/AEM.61.4.1507-1513.1995	journal	January 1995
Characterization of Sfp, a Bacillus subtilis Phosphopantetheinyl Transferase for Peptidyl Carrier Protein Domains in Peptide Synthetases ^† Quadri, Luis E. N.; Weinreb, Paul H.; Lei, Ming Biochemistry, Vol. 37, Issue 6 https://doi.org/10.1021/bi9719861	journal	February 1998
Bacterial Acetone Carboxylase Is a Manganese-dependent Metalloenzyme Boyd, Jeffrey M.; Ellsworth, Heather; Ensign, Scott A. Journal of Biological Chemistry, Vol. 279, Issue 45 https://doi.org/10.1074/jbc.M407177200	journal	August 2004
Ethylene and Agriculture: the Role of the Microbe Primrose, S. B. Journal of Applied Bacteriology, Vol. 46, Issue 1 https://doi.org/10.1111/j.1365-2672.1979.tb02579.x	journal	February 1979
The Purification and Properties of Cyclohexanone Oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871 Donoghue, Nuala A.; Norris, David B.; Trudgill, Peter W. European Journal of Biochemistry, Vol. 63, Issue 1 https://doi.org/10.1111/j.1432-1033.1976.tb10220.x	journal	March 1976
Aliphatic Epoxide Carboxylation Ensign, Scott A.; Allen, Jeffrey R. Annual Review of Biochemistry, Vol. 72, Issue 1 https://doi.org/10.1146/annurev.biochem.72.121801.161820	journal	June 2003
4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB: A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds Kamerbeek, Nanne M.; Moonen, Mariëlle J. H.; van der Ven, Jos G. M. European Journal of Biochemistry, Vol. 268, Issue 9 https://doi.org/10.1046/j.1432-1327.2001.02137.x	journal	May 2001
Carboxylic acid reductase is a versatile enzyme for the conversion of fatty acids into fuels and chemical commodities Akhtar, M. K.; Turner, N. J.; Jones, P. R. Proceedings of the National Academy of Sciences, Vol. 110, Issue 1, p. 87-92 https://doi.org/10.1073/pnas.1216516110	journal	December 2012
Isoprene: identified as a forest-type emission to the atmosphere Rasmussen, Reinhold A. Environmental Science & Technology, Vol. 4, Issue 8 https://doi.org/10.1021/es60043a008	journal	August 1970
Isolation and characterization of alkene-utilizing Xanthobacter spp. van Ginkel, C. G.; de Bont, J. A. M. Archives of Microbiology, Vol. 145, Issue 4 https://doi.org/10.1007/BF00470879	journal	September 1986
Microbial Synthesis of Alka(e)nes Wang, Weihua; Lu, Xuefeng Frontiers in Bioengineering and Biotechnology, Vol. 1 https://doi.org/10.3389/fbioe.2013.00010	journal	January 2013
Structural basis for carbon dioxide binding by 2-ketopropyl coenzyme M oxidoreductase/carboxylase Pandey, Arti S.; Mulder, David W.; Ensign, Scott A. FEBS Letters, Vol. 585, Issue 3 https://doi.org/10.1016/j.febslet.2010.12.035	journal	December 2010
Biochemistry of methanogenesis: a tribute to Marjory Stephenson:1998 Marjory Stephenson Prize Lecture Thauer, R. K. Microbiology, Vol. 144, Issue 9 https://doi.org/10.1099/00221287-144-9-2377	journal	September 1998
The Microbial Metabolism of Acetone Taylor, D. G.; Trudgill, P. W.; Cripps, R. E. Microbiology, Vol. 118, Issue 1 https://doi.org/10.1099/00221287-118-1-159	journal	May 1980
Plant surface lipid biosynthetic pathways and their utility for metabolic engineering of waxes and hydrocarbon biofuels Jetter, Reinhard; Kunst, Ljerka The Plant Journal, Vol. 54, Issue 4 https://doi.org/10.1111/j.1365-313X.2008.03467.x	journal	May 2008
Carcinogenic potential, levels and sources of polycyclic aromatic hydrocarbon mixtures in indoor and outdoor environments and their implications for air quality standards Delgado-Saborit, Juana Maria; Stark, Christopher; Harrison, Roy M. Environment International, Vol. 37, Issue 2 https://doi.org/10.1016/j.envint.2010.10.011	journal	February 2011
The Prodrug Activator EtaA from Mycobacterium tuberculosis Is a Baeyer-Villiger Monooxygenase Fraaije, Marco W.; Kamerbeek, Nanne M.; Heidekamp, Annelies J. Journal of Biological Chemistry, Vol. 279, Issue 5 https://doi.org/10.1074/jbc.M307770200	journal	January 2004
ChemInform Abstract: Cyclohexanone Monooxygenase: A Useful Reagent for Asymmetric Baeyer-Villiger Reactions Stewart, J. D. ChemInform, Vol. 29, Issue 44 https://doi.org/10.1002/chin.199844320	journal	November 1998
Cloning and Characterization of a Gene Cluster for Cyclododecanone Oxidation in Rhodococcus ruber SC1 Kostichka, Kristy; Thomas, Stuart M.; Gibson, Katharine J. Journal of Bacteriology, Vol. 183, Issue 21 https://doi.org/10.1128/JB.183.21.6478-6486.2001	journal	November 2001
Ecological, Behavioral, and Biochemical Aspects of Insect Hydrocarbons Howard, Ralph W.; Blomquist, Gary J. Annual Review of Entomology, Vol. 50, Issue 1 https://doi.org/10.1146/annurev.ento.50.071803.130359	journal	January 2005
Characterization of three protein components required for functional reconstitution of the epoxide carboxylase multienzyme complex from Xanthobacter strain Py2. Allen, J. R.; Ensign, S. A. Journal of Bacteriology, Vol. 179, Issue 10 https://doi.org/10.1128/JB.179.10.3110-3115.1997	journal	May 1997
Fate of the C1 product of propane dissimilation in Mycobacterium vaccae Coleman, J. P.; Perry, J. J. Journal of Bacteriology, Vol. 160, Issue 3 https://doi.org/10.1128/JB.160.3.1163-1164.1984	journal	December 1984
A role for coenzyme M (2-mercaptoethanesulfonic acid) in a bacterial pathway of aliphatic epoxide carboxylation Allen, J. R.; Clark, D. D.; Krum, J. G. Proceedings of the National Academy of Sciences, Vol. 96, Issue 15 https://doi.org/10.1073/pnas.96.15.8432	journal	July 1999
Unusual Coenzymes of Methanogenesis DiMarco, A. A.; Bobik, T. A.; Wolfe, R. S. Annual Review of Biochemistry, Vol. 59, Issue 1 https://doi.org/10.1146/annurev.bi.59.070190.002035	journal	June 1990
My Kind of Biology Wolfe, Ralph S. Annual Review of Microbiology, Vol. 45, Issue 1 https://doi.org/10.1146/annurev.mi.45.100191.000245	journal	October 1991
Mechanistic Implications of the Structure of the Mixed-Disulfide Intermediate of the Disulfide Oxidoreductase, 2-Ketopropyl-Coenzyme M Oxidoreductase/Carboxylase ^† ^, ^‡ Pandey, Arti S.; Nocek, Boguslaw; Clark, Daniel D. Biochemistry, Vol. 45, Issue 1 https://doi.org/10.1021/bi051518o	journal	January 2006
Purification and characterization of acetone carboxylase from Xanthobacter strain Py2 Sluis, M. K.; Ensign, S. A. Proceedings of the National Academy of Sciences, Vol. 94, Issue 16 https://doi.org/10.1073/pnas.94.16.8456	journal	August 1997
Purification to Homogeneity and Reconstitution of the Individual Components of the Epoxide Carboxylase Multiprotein Enzyme Complex from Xanthobacter Strain Py2 Allen, Jeffrey R.; Ensign, Scott A. Journal of Biological Chemistry, Vol. 272, Issue 51 https://doi.org/10.1074/jbc.272.51.32121	journal	December 1997
Incorporation of Oxygen from Water into Toluene and Benzene during Anaerobic Fermentative Transformation Vogel, Timothy M.; Grbìc-Galìc, Dunja Applied and Environmental Microbiology, Vol. 52, Issue 1 https://doi.org/10.1128/AEM.52.1.200-202.1986	journal	July 1986
New roles for CO 2 in the microbial metabolism of aliphatic epoxides and ketones Ensign, S. A.; Small, Frederick J.; Allen, Jeffrey R. Archives of Microbiology, Vol. 169, Issue 3 https://doi.org/10.1007/s002030050558	journal	February 1998
Synthesis of customized petroleum-replica fuel molecules by targeted modification of free fatty acid pools in Escherichia coli Howard, T. P.; Middelhaufe, S.; Moore, K. Proceedings of the National Academy of Sciences, Vol. 110, Issue 19 https://doi.org/10.1073/pnas.1215966110	journal	April 2013
Methyl Ketone Metabolism in Hydrocarbon-Utilizing Mycobacteria Lukins, H. B.; Foster, J. W. Journal of Bacteriology, Vol. 85, Issue 5 https://doi.org/10.1128/JB.85.5.1074-1087.1963	journal	May 1963
A single cytochrome P-450 system is involved in degradation of the herbicides EPTC (S-ethyl dipropylthiocarbamate) and atrazine by Rhodococcus sp. strain NI86/21 Nagy, I.; Compernolle, F.; Ghys, K. Applied and Environmental Microbiology, Vol. 61, Issue 5 https://doi.org/10.1128/AEM.61.5.2056-2060.1995	journal	May 1995
Biobased production of alkanes and alkenes through metabolic engineering of microorganisms Kang, Min-Kyoung; Nielsen, Jens Journal of Industrial Microbiology & Biotechnology, Vol. 44, Issue 4-5 https://doi.org/10.1007/s10295-016-1814-y	journal	August 2016
A novel ketone monooxygenase from Pseudomonas cepacia. Purification and properties Britton, L. N.; Markovetz, A. J. Journal of Biological Chemistry, Vol. 252, Issue 23 https://doi.org/10.1016/S0021-9258(19)75257-0	journal	December 1977
Alkene Monooxygenase from Xanthobacter Strain Py2 Small, Frederick J.; Ensign, Scott A. Journal of Biological Chemistry, Vol. 272, Issue 40 https://doi.org/10.1074/jbc.272.40.24913	journal	October 1997
mRNA Differential Display in a Microbial Enrichment Culture: Simultaneous Identification of Three Cyclohexanone Monooxygenases from Three Species Brzostowicz, Patricia C.; Walters, Dana M.; Thomas, Stuart M. Applied and Environmental Microbiology, Vol. 69, Issue 1 https://doi.org/10.1128/AEM.69.1.334-342.2003	journal	January 2003
Chemical Mechanisms of Catalytic Cracking over Solid Acidic Catalysts: Alkanes and Alkenes Kissin, Yury V. Catalysis Reviews, Vol. 43, Issue 1-2 https://doi.org/10.1081/CR-100104387	journal	May 2001
Widespread Head-to-Head Hydrocarbon Biosynthesis in Bacteria and Role of OleA Sukovich, D. J.; Seffernick, J. L.; Richman, J. E. Applied and Environmental Microbiology, Vol. 76, Issue 12 https://doi.org/10.1128/AEM.00436-10	journal	April 2010
Biochemistry of long-chain, nonisoprenoid hydrocarbons. III. Metabolic relation of long-chain fatty acids and hydrocarbons and other aspects of hydrocarbon metabolism in Sarcina lutea Albro, Phillip W.; Dittmer, John C. Biochemistry, Vol. 8, Issue 5 https://doi.org/10.1021/bi00833a022	journal	May 1969
Carboxylation of epoxides to beta-keto acids in cell extracts of Xanthobacter strain Py2 Allen, J. R.; Ensign, S. A. Journal of Bacteriology, Vol. 178, Issue 5 https://doi.org/10.1128/JB.178.5.1469-1472.1996	journal	March 1996
Acetone Formation in the Vibrio Family: a New Pathway for Bacterial Leucine Catabolism Nemecek-Marshall, Michele; Wojciechowski, Cheryl; Wagner, William P. Journal of Bacteriology, Vol. 181, Issue 24 https://doi.org/10.1128/JB.181.24.7493-7499.1999	journal	December 1999
Studies on the acetone-butyl alcohol fermentation Davies, Ronald; Stephenson, Marjory Biochemical Journal, Vol. 35, Issue 12 https://doi.org/10.1042/bj0351320	journal	December 1941
Cloning of Baeyer-Villiger monooxygenases from Comamonas, Xanthobacter and Rhodococcus using polymerase chain reaction with highly degenerate primers van Beilen, Jan B.; Mourlane, Frederic; Seeger, Markus A. Environmental Microbiology, Vol. 5, Issue 3 https://doi.org/10.1046/j.1462-2920.2003.00401.x	journal	March 2003
Discovery of a thermostable Baeyer–Villiger monooxygenase by genome mining Fraaije, Marco W.; Wu, Jin; Heuts, Dominic P. H. M. Applied Microbiology and Biotechnology, Vol. 66, Issue 4 https://doi.org/10.1007/s00253-004-1749-5	journal	October 2004
Purification and Properties of Cyclopentanone Oxygenase of Pseudomonas NCIB 9872 Griffin, Martin; Trudgill, Peter W. European Journal of Biochemistry, Vol. 63, Issue 1 https://doi.org/10.1111/j.1432-1033.1976.tb10222.x	journal	March 1976
A review on microbial synthesis of hydrocarbons Ladygina, N.; Dedyukhina, E. G.; Vainshtein, M. B. Process Biochemistry, Vol. 41, Issue 5 https://doi.org/10.1016/j.procbio.2005.12.007	journal	May 2006
Anaerobic bacterial metabolism of hydrocarbons Heider, Johann; Spormann, Alfred M.; Beller, Harry R. FEMS Microbiology Reviews, Vol. 22, Issue 5 https://doi.org/10.1111/j.1574-6976.1998.tb00381.x	journal	December 1998
Terminal Olefin (1-Alkene) Biosynthesis by a Novel P450 Fatty Acid Decarboxylase from Jeotgalicoccus Species Rude, Mathew A.; Baron, Tarah S.; Brubaker, Shane Applied and Environmental Microbiology, Vol. 77, Issue 5 https://doi.org/10.1128/AEM.02580-10	journal	January 2011

Similar Records

Novel Microbial Based Enzymatic CO₂ Fixation Mechanisms

Technical Report · Fri Apr 03 00:00:00 EDT 2020 · OSTI ID:1572716

A catalytic dyad modulates conformational change in the CO₂-fixing flavoenzyme 2-ketopropyl coenzyme M oxidoreductase/carboxylase

Journal Article · Thu Mar 31 00:00:00 EDT 2022 · Journal of Biological Chemistry · OSTI ID:1904773

The unique Phe–His dyad of 2-ketopropyl coenzyme M oxidoreductase/carboxylase selectively promotes carboxylation and S–C bond cleavage

Journal Article · Mon Jul 12 00:00:00 EDT 2021 · Journal of Biological Chemistry · OSTI ID:1816273

Related Subjects

Biochemistry & Molecular Biology

Insights into the unique carboxylation reactions in the metabolism of propylene and acetone

Citation Formats

References (85)

Similar Records

Related Subjects