Distinct Roles for Two CYP226 Family Cytochromes P450 in Abietane Diterpenoid Catabolism by
            <i>Burkholderia xenovorans</i>
            LB400

Smith, Daryl J.; Patrauchan, Marianna A.; Florizone, Christine; Eltis, Lindsay D.; Mohn, William W.

doi:10.1128/jb.01530-07

Cited by 15 publications

(15 citation statements)

References 42 publications

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“…On the other hand, we have confirmed here (see the "Substrate diverstity studies" section in Materials and Methods) that the CIB strain uses abietic acid, a model diterpene, as sole carbon source under aerobic conditions. It is known that the dit genes are responsible for diterpenes degradation in some bacteria via initial hydroxylating cytochrome P450s (peripheral pathway) and further meta-cleavage of the aromatic intermediate (central pathway) [48]. The dit genes are usually located within ICE elements [34], and we have found orthologous dit genes within a putative ICE DIT element in the genome of strain CIB (Figs.…”

Section: Genes For Aromatic Compounds Degradationmentioning

confidence: 94%

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Whole-genome analysis of Azoarcus sp. strain CIB provides genetic insights to its different lifestyles and predicts novel metabolic features

Martín‐Moldes

Zamarro

Cerro

et al. 2015

Systematic and Applied Microbiology

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The genomic features of Azoarcus sp. CIB reflect its most distinguishing phenotypes as a diazotroph, facultative anaerobe, capable of degrading either aerobically and/or anaerobically a wide range of aromatic compounds, including some toxic hydrocarbons such as toluene and m-xylene, as well as its endophytic lifestyle. The analyses of its genome have expanded the catabolic potential of strain CIB toward common natural compounds, such as certain diterpenes, that were not anticipated as carbon sources. The high number of predicted solvent efflux pumps and heavy metal resistance gene clusters has provided the first evidence for two environmentally relevant features of this bacterium that remained unknown. Genome mining has revealed several gene clusters likely involved in the endophytic lifestyle of strain CIB, opening the door to the molecular characterization of some plant growth promoting traits. Horizontal gene transfer and mobile genetic elements appear to have played a major role as a mechanism of adaptation of this bacterium to different lifestyles. This work paves the way for a systems biology-based understanding of the abilities of Azoarcus sp. CIB to integrate aerobic and anaerobic metabolism of aromatic compounds, tolerate stress conditions, and interact with plants as an endophyte of great potential for phytostimulation and phytoremediation strategies. Comparative genomics provides an Azoarcus pan genome that confirms the global metabolic flexibility of this genus, and suggests that its phylogeny should be revisited.

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Section: Genes For Aromatic Compounds Degradationmentioning

confidence: 94%

“…4). M a n u s c r i p t 9 In bacteria, some cyclic non-aromatic compounds, e.g., cyclohexane carboxylate, diterpenes, steroids, are channeled to aromatic central pathways through their degradation [18,34,48]. Azoarcus sp.…”

Section: Genes For Aromatic Compounds Degradationmentioning

confidence: 99%

Whole-genome analysis of Azoarcus sp. strain CIB provides genetic insights to its different lifestyles and predicts novel metabolic features

Martín‐Moldes

Zamarro

Cerro

et al. 2015

Systematic and Applied Microbiology

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“…Orthologous CYP226A encoding genes are found in a variety of bacteria that are known to degrade abietic acid derivatives, with minor differences in exact substrate specicity and function proposed. 42 In the operons encoding this pathway, the P450s are generally found associated with ferredoxin/ferredoxin reductase genes and in the case of CYP226A1 a co-encoded ferredoxin has been shown to support in vitro activity. 44 As with monoterpene utilisation, this complex pathway is initiated by P450 mediated hydroxylation.…”

Section: 38mentioning

confidence: 99%

“…5A). 41,42 The chemical necessity for C7 oxidation or for its placement early in the pathway are unclear. Orthologous CYP226A encoding genes are found in a variety of bacteria that are known to degrade abietic acid derivatives, with minor differences in exact substrate specicity and function proposed.…”

Section: 38mentioning

confidence: 99%

Unrivalled diversity: the many roles and reactions of bacterial cytochromes P450 in secondary metabolism

et al. 2018

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The cytochromes P450 (P450s) are a superfamily of heme-containing monooxygenases that perform diverse catalytic roles in many species, including bacteria. The P450 superfamily is widely known for the hydroxylation of unactivated C-H bonds, but the diversity of reactions that P450s can perform vastly exceeds this undoubtedly impressive chemical transformation. Within bacteria, P450s play important roles in many biosynthetic and biodegradative processes that span a wide range of secondary metabolite pathways and present diverse chemical transformations. In this review, we aim to provide an overview of the range of chemical transformations that P450 enzymes can catalyse within bacterial secondary metabolism, with the intention to provide an important resource to aid in understanding of the potential roles of P450 enzymes within newly identified bacterial biosynthetic pathways. 1.Introduction to P450s 2.Chemistry of P450 enzymes 3.Bacterial biosynthesis pathways involving P450s 3.1Terpene metabolism 3.1. Battersby (1925Battersby ( -2018 to the molecular understanding of biosynthesis over the course of their careers.

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“…The number of described microbial P450 enzymes that can be used for the biotransformation of diterpenoid substrates is still limited. Recently, two members of the CYP226 family able to hydroxylate different abietane-type diterpenoids could be identified in Burkholderia xenovorans LB400 [71]. This proteobacterium is well known for its noncatabolic physiological adaptation to organic compounds and both CYP226 enzymes have distinct roles in the abietane catabolism.…”

Section: Resin Acid Diterpenoidsmentioning

confidence: 99%

Terpene Hydroxylation with Microbial Cytochrome P450 Monooxygenases

Janocha

Schmitz

Bernhardt

2015

Biotechnology of Isoprenoids

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Terpenoids comprise a highly diverse group of natural products. In addition to their basic carbon skeleton, they differ from one another in their functional groups. Functional groups attached to the carbon skeleton are the basis of the terpenoids' diverse properties. Further modifications of terpene olefins include the introduction of acyl-, aryl-, or sugar moieties and usually start with oxidations catalyzed by cytochrome P450 monooxygenases (P450s, CYPs). P450s are ubiquitously distributed throughout nature, involved in essential biological pathways such as terpenoid biosynthesis as well as the tailoring of terpenoids and other natural products. Their ability to introduce oxygen into nonactivated C-H bonds is unique and makes P450s very attractive for applications in biotechnology. Especially in the field of terpene oxidation, biotransformation methods emerge as an attractive alternative to classical chemical synthesis. For this reason, microbial P450s depict a highly interesting target for protein engineering approaches in order to increase selectivity and activity, respectively. Microbial P450s have been described to convert industrial and pharmaceutically interesting terpenoids such as ionones, limone, valencene, resin acids, and triterpenes (including steroids) as well as vitamin D3. Highly selective and active mutants have been evolved by applying classical site-directed mutagenesis as well as directed evolution of proteins. As P450s usually depend on electron transfer proteins, mutagenesis has also been applied to improve the interactions between P450s and their respective redox partners. This chapter provides an overview of terpenoid hydroxylation reactions catalyzed by bacterial P450s and highlights the achievements made by protein engineering to establish productive hydroxylation processes.

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Distinct Roles for Two CYP226 Family Cytochromes P450 in Abietane Diterpenoid Catabolism by Burkholderia xenovorans LB400

Cited by 15 publications

References 42 publications

Whole-genome analysis of Azoarcus sp. strain CIB provides genetic insights to its different lifestyles and predicts novel metabolic features

Whole-genome analysis of Azoarcus sp. strain CIB provides genetic insights to its different lifestyles and predicts novel metabolic features

Unrivalled diversity: the many roles and reactions of bacterial cytochromes P450 in secondary metabolism

Terpene Hydroxylation with Microbial Cytochrome P450 Monooxygenases

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