CYP108N14: A Monoterpene Monooxygenase from Rhodococcus globerulus

Giang, Peter D.; Churchman, Luke R.; Buczynski, Julia B.; Bell, Stephen G.; Stok, Jeanette E.; De Voss, James J.

doi:10.1016/j.abb.2023.109852

Cited by 4 publications

(1 citation statement)

References 41 publications

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“…Additionally, this experimental work confirms that pinene is more reactive than limonene, and one of the main products resulting from the oxidation of both limonene and pinene under similar conditions are their allylic derivatives (Table 1, entries: 16 [40], 23 [47], 25 [52], 26 [51]). In turn, in the case of cymene and limonene and using the same reaction conditions, these monoterpenes were found to oxidize at carbon C7 [9,91]. Interestingly, in the case of both monoterpenes, the calculated BDE values for these bonds are comparable (Tables S2 and S3).…”

Section: Gasmentioning

confidence: 76%

DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

Rydel-Ciszek

2024

Molecules

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Nowadays, the effective processing of natural monoterpenes that constitute renewable biomass found in post-production waste into products that are starting materials for the synthesis of valuable compounds is a way to ensure independence from non-renewable fossil fuels and can contribute to reducing global carbon dioxide emissions. The presented research aims to determine, based on DFT calculations, the activity and reactivity of limonene, an organic substrate used in previous preparative analyses, in comparison to selected monoterpenes such as cymene, pinene, thymol, and menthol. The influence of the solvent model was also checked, and the bonds most susceptible to reaction were determined in the examined compounds. With regard to EHOMO, it was found that limonene reacts more easily than cymene or menthol but with more difficultly than thymol and pienene. The analysis of the global chemical reactivity descriptors “locates” the reactivity of limonene in the middle of the studied monoterpenes. It was observed that, among the tested compounds, the most reactive compound is thymol, while the least reactive is menthol. The demonstrated results can be a reference point for experimental work carried out using the discussed compounds, to focus research on those with the highest reactivity.

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Section: Gasmentioning

confidence: 76%

DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

Rydel-Ciszek

2024

Molecules

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Production of derivatives of α-terpineol by bacterial CYP102A1 enzymes

Kim,

Park,

Jeong

et al. 2024

Biotechnol Lett

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Bioinformatics Analysis of the Genome of Rhodococcus rhodochrous IEGM 1362, an (−)-Isopulegol Biotransformer

Maltseva,

Plotnitskaya,

Krivoruchko

et al. 2024

Genes

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A genome of Rhodococcus rhodochrous IEGM 1362 was sequenced and annotated. This strain can transform monoterpene alcohol (–)-isopulegol with the formation of two novel pharmacologically promising metabolites. Nine genes encoding cytochrome P450, presumably involved in (–)-isopulegol transformation, were found in the genome of R. rhodochrous IEGM 1362. Primers and PCR conditions for their detection were selected. The obtained data can be used for the further investigation of genes encoding enzymes involved in monoterpene biotransformation.

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CYP108N14: A Monoterpene Monooxygenase from Rhodococcus globerulus

Cited by 4 publications

References 41 publications

DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

DFT Studies of the Activity and Reactivity of Limonene in Comparison with Selected Monoterpenes

Production of derivatives of α-terpineol by bacterial CYP102A1 enzymes

Bioinformatics Analysis of the Genome of Rhodococcus rhodochrous IEGM 1362, an (−)-Isopulegol Biotransformer

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