Biotransformation of codeine to 14-OH-codeine derivatives by Rhizobium radiobacter R89-1

Kyslíková, Eva; Babiak, Peter; Štěpánek, Václav; Zahradník, Jiří; Palyzová, Andrea; Marešová, Helena; Valešová, Renáta; Hájíček, Josef; Kyslı́k, Pavel

doi:10.1016/j.molcatb.2012.10.004

Cited by 14 publications

(7 citation statements)

References 26 publications

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“…The Agrobacterium sp. strain R89-1 was originally isolated from composted poppy seed wastes ( Papaver somniferum ) in the central Bohemia region (Neratovice, Agro Býškovice) as a nonphytopathogenic strain capable of codeine 14-OH biotransformation ( 1 ). The strain was deposited in the Czech Collection of Microorganisms (CCM) with the number CCM 7949.…”

Section: Genome Announcementmentioning

confidence: 99%

Draft Genome Sequence of Agrobacterium sp. Strain R89-1, a Morphine Alkaloid-Biotransforming Bacterium

2016

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Section: Genome Announcementmentioning

confidence: 99%

Draft Genome Sequence of Agrobacterium sp. Strain R89-1, a Morphine Alkaloid-Biotransforming Bacterium

2016

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“…bohemicum R89-1 [ 18 ]. We reported a hydroxylation of codeine at the carbon C14 [ 19 ], and a later genomic and biochemical study identified the OYE enzyme currently named XdpB. XdpB has the activity of morphinone reductase and catalyzes hydrogenation of the codeinone C7-C8 double bond [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

The crystal structure of XdpB, the bacterial old yellow enzyme, in an FMN-free form

et al. 2018

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Old Yellow Enzymes (OYEs) are NAD(P)H dehydrogenases of not fully resolved physiological roles that are widespread among bacteria, plants, and fungi and have a great potential for biotechnological applications. We determined the apo form crystal structure of a member of the OYE class, glycerol trinitrate reductase XdpB, from Agrobacterium bohemicum R89-1 at 2.1 Å resolution. In agreement with the structures of the related bacterial OYEs, the structure revealed the TIM barrel fold with an N-terminal β-hairpin lid, but surprisingly, the structure did not contain its cofactor FMN. Its putative binding site was occupied by a pentapeptide TTSDN from the C-terminus of a symmetry related molecule. Biochemical experiments confirmed a specific concentration-dependent oligomerization and a low FMN content. The blocking of the FMN binding site can exist in vivo and regulates enzyme activity. Our bioinformatic analysis indicated that a similar self-inhibition could be expected in more OYEs which we designated as subgroup OYE C1. This subgroup is widespread among G-bacteria and can be recognized by the conserved sequence GxxDYP in proximity of the C termini. In proteobacteria, the C1 subgroup OYEs are typically coded in one operon with short-chain dehydrogenase. This operon is controlled by the tetR-like transcriptional regulator. OYEs coded in these operons are unlikely to be involved in the oxidative stress response as the other known members of the OYE family because no upregulation of XdpB was observed after exposing A. bohemicum R89-1 to oxidative stress.

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“…Morphine alkaloids are important class of pharmaceutical substances because of their powerful analgesic (Bruce et al, 1990;Lister et al, 1999;Niknam et al, 2010), antitussive and narcotic antagonist characteristics (Kyslíková et al 2013). Papaver somniferum (opium poppy), a traditional source of morphine alkaloids (Kyslíková et al 2013;Nyman, 1978), with secondary metabolites accumulate at low level in plant as a sole commercial resource (Nakagawa et al, 2011;Nyman, 1978). Syntheses of these compounds were difficult and time consuming due to their complexity and strict regulation of biosynthesis morphine alkaloids pathways (Nakagawa et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

“…In addition to plant, microorganisms have ultimate potential to operate selective biochemical transformations (Rathbone and Bruce, 2002). There are many reports on the production of morphine alkaloids from fungi and bacteria including the genus Trametes (Boonstra et al, 2001;Bruce et al, 1990;Hailes and Bruce, 1993;Kunz et al, 1985;Kyslíková et al, 2013;Long et al, 1995;Madyastha et al, 2000;Niknam et al, 2010), Cunninghamella (Abel et al, 2002;Asha and Vidyavathi, 2009;Boonstra et al, 2001;Bruce et al, 1990;Hartman et al, 1964;Kunz et al, 1985;Kyslíková et al, 2013;Niknam et al, 2010), Mucor piriformis (Kyslíková et al, 2013;Madyastha et al, 2000;Abel et al, 2002;Chaudhary et al, 2009), and Cylindrocarpon didymum (Boonstra et al, 2001;Rathbone and Bruce, 2002;Stabler et al, 2001); in a group of fungi and Arthrobacter sp. (Boonstra et al, 2001;Hailes and Bruce, 1993;Kunz et al, 1985;Kyslíková et al, 2013;Long et al, 1995;Niknam et al, 2010), Pseudomonas testosteroni (Boonstra et al, 2001;Hailes and Bruce, 1993;Kunz et al, 1985;Kyslíková et al, 2013;Rathbone and Bruce, 2002), Pseudomonas putida (Boonstra et al, 2001;Bruce et al, 1990;Hailes and Bruce, 1993;…”

Section: Introductionmentioning

confidence: 99%

Biocatalysts screening of Papaver bracteatum flora for thebaine transformation to codeine and morphine

Ataee

Fooladi

Namaei

et al. 2017

Biocatalysis and Agricultural Biotechnology

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The aim of this study was to find biocatalyst which uses thebaine and extract of different parts of Papaver bracteatum to synthesize morphine alkaloids. The thebaine-resistant strains were obtained from microbial flora of different parts of P.bracteatum. They were purified and treated utilizing different concentrations of thebaine. Those that can grow at a concentration of over 500 µg/ml were chosen for the biotransformation experiments. Biotransformation experiments were carried out utilizing selected cells in the medium containing thebaine and/ or the extract of P.bracteatum; the products of such biotransformation were extracted and the profiles of metabolites were evaluated using HPTLC, and LC/ESI-MS methods. Thereafter, the effective isolate for thebaine transformation was characterized by physiological, biochemical and biomolecular methods. The results show that among 67 isolates, 12 strains were selected using the HPTLC screening as candidates that can transform thebaine into codeine and morphine. Among them, 5 strains were identified to transform plant extract, among which, using LC/ESI-MS, a candidate was selected and identified as Bacillus sp. FAR. It can be concluded from this study, that this microbial flora candidate can transform thebaine into important narcotic drugs and it will be a valuable step in biotechnology.

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Biotransformation of codeine to 14-OH-codeine derivatives by Rhizobium radiobacter R89-1

Cited by 14 publications

References 26 publications

Draft Genome Sequence of Agrobacterium sp. Strain R89-1, a Morphine Alkaloid-Biotransforming Bacterium

Draft Genome Sequence of Agrobacterium sp. Strain R89-1, a Morphine Alkaloid-Biotransforming Bacterium

The crystal structure of XdpB, the bacterial old yellow enzyme, in an FMN-free form

Biocatalysts screening of Papaver bracteatum flora for thebaine transformation to codeine and morphine

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