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Topic: Morphinone


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In the News (Fri 18 Dec 09)

  
  World Intellectual Property Organization   (Site not responding. Last check: 2007-10-15)
It is a further object of certain embodiments of the present invention to provide a method for detecting morphinone in a hydromorphone preparation when the morphinone is present in the preparation in an amount of less than 500 ppm.
The peak area of morphinone from the high concentration first sample solution, and the peak area of hydromorphone from the lower concentration second sample solution can be used to calculate the amount (e.
The morphinone peak was identified using the relative retention time for morphinone (see Table 1 above), and the amount of morphinone was quantified according to the calculation below.
www.wipo.int /ipdl/IPDL-CIMAGES/view/pct/getbykey5?KEY=05/16930.050224&ELEMENT_SET=DECL   (5232 words)

  
 [No title]
Morphinone (XI) is of interest, since it may be postulated that it is a biogenetic precursor of certain morphine alkaloids - e.g., morphine itself could be formed by reduction of (XI), codeine could be formed by reduction and methylation and thebaine would result by dehydrogenation and dimethylation (4).
Rapoport and his co-workers (5) have recently prepared this sensitive ketone (XI) by oxidation of morphine whose phenolic group was protected with a methoxymethyl group (IX), by means of silver carbonate in benzene.
Reduction of morphinone with sodium borohydride was possible and gave morphine.
www.unodc.org /unodc/en/bulletin/bulletin_1959-01-01_3_page002.html?print=yes   (1222 words)

  
 Ps. putida
M10, catalyses the NADH-dependent saturation of the carbon-carbon double bond of morphinone and codeinone, and is believed to be involved in the metabolism of morphine and codeine.
Sequence analysis and structural characteristics indicated that morphinone reductase is related to the flavoprotein alpha/beta-barrel oxidoreductases, and is particularly similar to Old Yellow Enzyme of Saccharomyces spp.
Morphinone reductase was overexpressed in Escherichia coli, and has potential applications for the industrial preparation of semisynthetic opiates.
www.bionewsonline.com /m/1/pseudomonas_putida_c.htm   (17762 words)

  
 Biotransformation of Explosives by the Old Yellow Enzyme Family of Flavoproteins -- Williams et al. 70 (6): 3566 -- ...
substrates of PETN reductase (PETN, GTN, and TNT), morphinone
Crystal structure of bacterial morphinone reductase and properties of the C191A mutant enzyme.
Messiha, H. L., Munro, A. W., Bruce, N. C., Barsukov, I., Scrutton, N. Reaction of Morphinone Reductase with 2-Cyclohexen-1-one and 1-Nitrocyclohexene: PROTON DONATION, LIGAND BINDING, AND THE ROLE OF RESIDUES HISTIDINE 186 AND ASPARAGINE 189.
aem.asm.org /cgi/content/full/70/6/3566   (3656 words)

  
 ICPP98 Paper Number 1.6.5   (Site not responding. Last check: 2007-10-15)
A 600-bp PCR fragment, amplified with primers derived from the morB sequence of P.
putida, enzymatic activity was measured with morphinone, codeinone, neopinone and 2-cyclohexen-1-one as substrates [2].
Several alkaloids and phytoalexins are produced by plants and possess antimicrobial activity.
www.bspp.org.uk /ICPP98/1.6/5.html   (384 words)

  
 University of Leicester Biochemistry Department
The closely related flavo-enzymes Morphinone reductase (from Psuedomonas putida M10) and PETN reductase (pentaerythritol tetranitrate reductase from Enterobacter cloacae PB2) have applications for both biotransformations and in sensors.
Morphinone reductase catalyses the saturation of the carbon-carbon double bond of the alkaloids morphinone and codeinone with oxidation of NADH on the pathway that converts morphine to hydromorphone.
Scrutton, & PCE Moody (2002) Crystal Structure of Bacterial Morphinone Reductase and Properties of the C191A Mutant Enzyme.
www.le.ac.uk /biochem/research/pcem1_r.html   (1797 words)

  
 Cofactor Regeneration by a Soluble Pyridine Nucleotide Transhydrogenase for Biological Production of Hydromorphone -- ...
morphinone reductase (MR) (5, 6, 8, 12) (Fig.
Microbial degradation of the morphine alkaloids: identification of morphinone as an intermediate in the metabolism of morphine by Pseudomonas putida M10.
Purification and characterisation of morphinone reductase from Pseudomonas putida M10.
aem.asm.org /cgi/content/full/66/12/5161   (3282 words)

  
 Biological Production of Semisynthetic Opiates Using Genetically Engineered Bacteria - Nature Biotechnology   (Site not responding. Last check: 2007-10-15)
Brace, N.C., Wilmot, C.J., Jordan, K.N., Trebilcock, A.E., Gray Stephens, L.D. and Lowe, C.R. Microbial degradation of the morphine alkaloids: identification of morphinone as an intermediate in the metabolism of morphine by Pseudomonas putida M10.
French, C.E. and Bruce, N.C. Purification and characterisation of morphinone reductase from Pseudomonas putida M10.
French, C.E. and Bruce, N.C. Bacterial morphinone reductase is related to Old Yellow Enzyme and related eukaryotic proteins.
www.nature.com /nbt/journal/v13/n7/abs/nbt0795-674.html   (545 words)

  
 In vivo formation of codeinone and morphinone from codeine. Isolation and identification from guinea pig bile -- Ishida ...
Isolation and identification from guinea pig bile -- Ishida et al.
Articles by Ishida, T. Articles by Toki, S. In vivo formation of codeinone and morphinone from codeine.
Codeinone (CO) and morphinone (MO) were isolated and identified in the bile
dmd.aspetjournals.org /cgi/content/abstract/19/5/895   (217 words)

  
 University of Leicester Depatment of Biochemistry   (Site not responding. Last check: 2007-10-15)
[143] Hydrogen tunneling in the multiple H-transfers of the catalytic cycle of morphinone reductase and in the reductive half-reaction of the homologous pentaerythritol tetranitrate reductase (2003).
[63] Reductive and oxidative half-reactions of morphinone reductase from Pseudomonas putida M10: a kinetic and thermodynamic analysis (1998).
[57] Crystallization and preliminary diffraction studies of morphinone reductase, a flavoprotein involved in the degradation of morphine alkaloids (1997).
www.le.ac.uk /biochem/staff/nss4/nss4_4.html   (5554 words)

  
 University of Leicester Depatment of Biochemistry
DH Craig, T Barna, PCE Moody, NC Bruce, SK Chapman, AW Munro & NS Scrutton (2001) Effects of environment on flavin reactivity in morphinone reductase: analysis of enzymes displaying differential charge near the N1 atom and C2 carbonyl region of the active site flavin.
TM Barna, H Khan, NC Bruce, I Barsukov, NS Scrutton, & PCE Moody (2001) Crystal structure of pentaerythritol tetranitrate reductase: "Flipped" binding geometries for steroid substrates in different redox states of the enzyme.
(1997) Crystallisation and preliminary diffraction studies of morphinone reductase, a flavoprotein involved in the degradation of morphine alkaloids.
www.le.ac.uk /biochem/staff/pcem1/pcem1.html   (984 words)

  
 Thermoregulated Expression and Characterization of an NAD(P)H-Dependent 2-Cyclohexen-1-one Reductase in the Plant ...
N-terminal sequence homology to morphinone reductase (MR) of Pseudomonas
Several substances with structural similarities to morphinone and 2-cyclohexen-1-one were tested as potential substrates for
Reductive and oxidative half-reactions of morphinone reductase from Pseudomonas putida M10: a kinetic and thermodynamic analysis.
jb.asm.org /cgi/content/full/181/3/814   (5032 words)

  
 Kinetic and Structural Basis of Reactivity of Pentaerythritol Tetranitrate Reductase with NADPH, 2-Cyclohexenone, ...
OYE (26) and bacterial morphinone reductase (27) and is shown
Reaction of Morphinone Reductase with 2-Cyclohexen-1-one and 1-Nitrocyclohexene: PROTON DONATION, LIGAND BINDING, AND THE ROLE OF RESIDUES HISTIDINE 186 AND ASPARAGINE 189
H-tunneling in the Multiple H-transfers of the Catalytic Cycle of Morphinone Reductase and in the Reductive Half-reaction of the Homologous Pentaerythritol Tetranitrate Reductase
www.jbc.org /cgi/content/full/277/24/21906   (4963 words)

  
 Reductive and Oxidative Half-Reactions of Morphinone Reductase from Pseudomonas putida M10: A Kinetic and Thermodynamic ...   (Site not responding. Last check: 2007-10-15)
Department of Biochemistry, University of Leicester, Adrian Building, University Road, Leicester LE1 7RH U.K., and Institute of Biotechnology, University of Cambridge, Tennis Court Road, Cambridge CB2 1TP
The reaction of morphinone reductase (MR) with the physiological reductant NADH and the oxidizing substrate codeinone has been studied by multiple and single wavelength stopped-flow spectroscopy.
Although common features are identified, there are notable differences in the kinetic and redox properties of the two enzymes.
pubs.acs.org /cgi-bin/abstract.cgi/bichaw/1998/37/i20/abs/bi980345i.html   (396 words)

  
 PhD | Project Details
Projects available are of two general types, one is the determination of new structures, such as those of morphinone reductase and PETN reductase (flavoenzymes important for the biosynthesis of opiates and bioremediation of explosives), Nodl (involved in nitrogen fixation) and 'XAT' (involved in antibiotic resistance).
The other is the detailed examination of the interactions of interesting ligands with a protein for which the structure is already known, e.g..
Structure 5, 623-633 ; Moody P C E, Shikotra N, French C E, Bruce N C and Scrutton N S (1997) Crystallisation and preliminary diffraction studies of morphinone reductase, a flavoprotein involved in the degradation of morphine alkaloids.
www.findaphd.com /search/showproject.asp?projectid=1488   (652 words)

  
 Crystal Structure of Bacterial Morphinone Reductase and Properties of the C191A Mutant Enzyme -- Barna et al. 277 (34): ...
Crystal Structure of Bacterial Morphinone Reductase and Properties of the C191A Mutant Enzyme -- Barna et al.
The crystal structure of the NADH-dependent bacterial flavoenzyme morphinone reductase (MR) has been determined at 2.2-Å resolution
with the genes encoding morphinone reductase and morphine dehydrogenase
www.jbc.org /cgi/content/full/277/34/30976   (5012 words)

  
 Untitled   (Site not responding. Last check: 2007-10-15)
It has been found that the introduction of a simple alkyl group (i.e.
ethyl) at the 14-position of morphinone greatly increases its agonist potency.
During the continuing study on potent and selective opioid receptor ligands, we have synthesized 14-(3'-phenylpropyl)-dihydrocodeinone, dihydromorphinone, their N-cyclopropylmethyl analogs and the corresponding indole derivatives by using a thebaine Diels-Alder reaction with phenyl vinyl ketone.
www.cpdd.vcu.edu /98abs/tian.html   (198 words)

  
 PHA 4220 - Neurology Pharmacotherapeutics
Conversion of the 6-OH to a 6-OCH3, yielding heterocodeine, results in a six-fold increase in activity.
Oxidation of the 6-OH to a ketone reduces activity when the 7,8-double bond is present (morphinone = 37% of morphine).
However, as shown below, when the 7,8-double bond is saturated, a 6-keto will increase activity.
wiz2.pharm.wayne.edu /module/opioid.html   (1790 words)

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