ArticleJournal of bacteriology1999
Purification of a glutathione S-transferase and a glutathione conjugate-specific dehydrogenase involved in isoprene metabolism in Rhodococcus sp. strain AD45.
Article in Journal of bacteriology, 1999. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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35 citing papers in PubMed, 74 citations in OpenAlex.
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- Biodegradation of isoprene by soil Actinomycetota from coffee-tea integrated plantations in a tropical evergreen forest.Current research in microbial sciences · 2025Article
- Analysis of Essential Isoprene Metabolic Pathway Proteins inApplied and environmental microbiology · 2023Article
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- 'Omics-guided prediction of the pathway for metabolism of isoprene by Variovorax sp. WS11.Environmental microbiology · 2022Article
- Purification and Characterization of the Isoprene Monooxygenase fromApplied and environmental microbiology · 2022Article
- Genome Characterisation of an Isoprene-DegradingBiology · 2022Article
- Characterization of the GlutathioneMicrobiology spectrum · 2021Article
- Isoprene-degrading bacteria associated with the phyllosphere of Salix fragilis, a high isoprene-emitting willow of the Northern Hemisphere.Environmental microbiome · 2021Article
- Current Advances in the Bacterial Toolbox for the Biotechnological Production of Monoterpene-Based Aroma Compounds.Molecules (Basel, Switzerland) · 2020Review
- Microbial metabolism of isoprene: a much-neglected climate-active gas.Microbiology (Reading, England) · 2020Review
- Molecular Ecology of Isoprene-Degrading Bacteria.Microorganisms · 2020Review
- Complete Genome of Isoprene DegradingMicroorganisms · 2020Article
- Isoprene Oxidation by the Gram-Negative Model bacteriumMicroorganisms · 2020Article
- Actinobacterial Degradation of 2-Hydroxyisobutyric Acid Proceeds via Acetone and Formyl-CoA by Employing a Thiamine-Dependent Lyase Reaction.Frontiers in microbiology · 2020Article
- Reductive metabolism of the important atmospheric gas isoprene by homoacetogens.The ISME journal · 2019Article
- Novel Isoprene-Degrading Proteobacteria From Soil and Leaves Identified by Cultivation and Metagenomics Analysis of Stable Isotope Probing Experiments.Frontiers in microbiology · 2019Article
- Poplar phyllosphere harbors disparate isoprene-degrading bacteria.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
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4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A glutathione S-transferase (GST) with activity toward 1, 2-epoxy-2-methyl-3-butene (isoprene monoxide) and cis-1, 2-dichloroepoxyethane was purified from the isoprene-utilizing bacterium Rhodococcus sp. strain AD45. The homodimeric enzyme (two subunits of 27 kDa each) catalyzed the glutathione (GSH)-dependent ring opening of various epoxides. At 5 mM GSH, the enzyme followed Michaelis-Menten kinetics for isoprene monoxide and cis-1, 2-dichloroepoxyethane, with Vmax values of 66 and 2.4 micromol min-1 mg of protein-1 and Km values of 0.3 and 0.1 mM for isoprene monoxide and cis-1,2-dichloroepoxyethane, respectively. Activities increased linearly with the GSH concentration up to 25 mM. 1H nuclear magnetic resonance spectroscopy showed that the product of GSH conjugation to isoprene monoxide was 1-hydroxy-2-glutathionyl-2-methyl-3-butene (HGMB). Thus, nucleophilic attack of GSH occurred on the tertiary carbon atom of the epoxide ring. HGMB was further converted by an NAD+-dependent dehydrogenase, and this enzyme was also purified from isoprene-grown cells. The homodimeric enzyme (two subunits of 25 kDa each) showed a high activity for HGMB, whereas simple primary and secondary alcohols were not oxidized. The enzyme catalyzed the sequential oxidation of the alcohol function to the corresponding aldehyde and carboxylic acid and followed Michaelis-Menten kinetics with respect to NAD+ and HGMB. The results suggest that the initial steps in isoprene metabolism are a monooxygenase-catalyzed conversion to isoprene monoxide, a GST-catalyzed conjugation to HGMB, and a dehydrogenase-catalyzed two-step oxidation to 2-glutathionyl-2-methyl-3-butenoic acid.
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