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Topic: Codeinone



  
 Method for Producing Oxycodone
Optimal oxidation conditions may vary with different organosilyl ethers.
The trimethylsilyl ether, however, was found to be rapidly hydrolyzed.
(a) producing a dienol organosilyl ether at position 6 of the C-ring of codeinone thereby forming a dienol organosilyl ether congener of codeinone;
http://www.poppies.org/news/99502129975371.shtml

  
 Patent 4054566: Process for converting neopinone to codeinone
Neopine is one of the alkaloids available from the opium poppy and it can readily be converted to neopinone.
Likewise neopinone may be obtained from thebaine alkaloid according to the procedure described in our co-pending application entitled Metallic Derivatives of Neopinone Ketal, Serial No. 665,601, filed on the same date herewith.
treating the 8-halodihydrocodeinone hydrochloride with a basic agent to form codeinone.
http://www.freepatentsonline.com/4054566.html

  
 Codeine And Morphine: Advantages Of Morphine Pump on Popular Links
morphine addiction Pathways reducing codeinone to codeine and morphinone to morphine.
Codeinone reductase has.Most common are morphine sulfate and ethex morphine image morphine hydrochloride.
Effects similar to morphine except euphoria is similar to codeine nausea and vomiting is.1 Pupil diameter gradually returned to baseline values over the course of the remainder of the study
http://codeine-and-morphine.popularlinks.info

  
 Current Medicinal Chemistry, Volume 11, No. 19, 2004
In this work a review is given on the present status of oxime pharmacology, chemistry and analysis and also the oxime and O-methyl oxime formation of 6-oxo-morphinanes with therapeutic interest (codeinone, oxycodone, hydrocodone and 14-OH-codeinone).
The oxime formation was monitored by reversed-phase HPLC and the chromatographic properties of oxime isomers have been characterized.
http://www.bentham.org/cmc/cmc11-19.htm

  
 ANESTH.OR.JP INFORMATION
Codeinone did not significantly change the MnSOD activity nor its mRNA expression.
Fluorometric assay showed that codeinone time-dependently activatied caspase 3 and 9, but not caspase 8, suggesting the activation of intrinsic apoptotic signaling pathway via mitochondria.
FACS analysis demonstrated that codeinone induced the production of ANNEXIN-positive apoptotic cells in human cancer cells (HL-60, MCF7, A549).
http://kansai.anesth.or.jp/kako/masui50/abstract/E1-03.html

  
 The Scientist :: RNAi turns poppies off morphine, Nov. 15, 2004
Larkin and colleagues employed RNA interference to silence codeinone reductase (COR), the penultimate enzyme in morphine biosynthesis, and shed light on pathway controls.
Larkin and colleagues suggest the unexpected reticuline phenotype may have been caused by a buildup of morphine substrates codeinone and neopinione that triggered negative feedback on one or more earlier enzymes or transport steps of the morphine branch.
The enzymology of the entire morphine pathway is largely elucidated, but virtually nothing is known of what regulates the accumulation of morphine and its intermediates in poppies.
http://www.biomedcentral.com/news/20041115/01

  
 Codeinone - Wikipedia, the free encyclopedia
{Alfentanil} {Buprenorphine} {Carfentanil} {Codeine} {Codeinone} {Dextropropoxyphene} {Dihydrocodeine} {Endorphin} {Fentanyl} {Heroin} {Hydrocodone} {Hydromorphone} {Methadone} {Morphine} {Morphinone} {Oxycodone} {Oxymorphone} {Pethidine} {Remifentanil} {Sufentanil} {Thebaine} {Tramadol}
Codeinone can be also described as the Ketone of Codeine: Codein-6-on
Codeinone can described as the methylether of morphinone: 3-Methyl-morphinone.
http://www.wikipedia.org/wiki/Codeinone

  
 Tramadol, buy tramadol, antibiotics, Weight Loss drugs, weight loss herbs, weight loss herbal formula, hair loss, hair ...
A study of structurally-related compounds suggested that the alpha,beta-unsaturated ketone group of codeinone was responsible for its antitumor cytotoxicity.
The cytotoxic activity of codeinone was significantly reduced by N-acetylcysteine, but not affected by FeCl3, CuCl2, CoCl2, sodium ascorbate or catalase.
Human oral gingival fibroblasts (HGF) were relatively resistant to codeinone, as judged by higher SI ratio (3.7) suggesting the tumor-selective cytotoxicity of codeinone.
http://www.hair-loss-stop.com/ref-cysteine/cysteine-research-abs5.337.html

  
 Molecular Characterization of the Salutaridinol 7-O-Acetyltransferase Involved in Morphine Biosynthesis in Opium Poppy ...
of the morphine pathway that reduces codeinone to codeine (13).
This is in stark contrast to the other known morphine-specific biosynthetic gene cor1 encoding codeinone reductase for which
The number of restriction endonuclease recognition sites that occur within the open reading frame are as follows: EcoRI, 0; HindIII, 0; ApoI, 1; SalI, 1; SpeI, 1; HincII, I; and MspI, 3.
http://www.jbc.org/cgi/content/full/276/33/30717

  
 codeinone
Rofecoxib } { Indomethacin } Opioids edit { Alfentanil } { Buprenorphine } { Carfentanil } { Codeine } { Codeinone } { Dextropropoxyphene } { Dihydrocodeine } { Endorphin } { Fentanyl } { Heroin } { Hydrocodone } { Hydromorphone...
are salutaridinol 7- O -acetyltransferase and codeinone reductase the penultimate enzyme of the morphine pathway that reduces codeinone to codeine.
Given the number of cDNAs specific to various alkaloid...
http://codeinone.networklive.org

  
 Crystal Structure of Bacterial Morphinone Reductase and Properties of the C191A Mutant Enzyme -- Barna et al. 277 (34): ...
to hydride transfer to codeinone (consistent with our previous
the oxidative half-reaction when codeinone is used as the oxidizing
site, and further codeinone soaking steps were tried.
http://www.jbc.org/cgi/content/full/277/34/30976

  
 UNODC - Bulletin on Narcotics - 1950 Issue 2 - 003
Codeine itself is oxidized into codeinone, and the methyl ether of the enol form of this is the same as thebaine.
[43] Codeinone, for example, does not react even at 170 degrees, at which temperature a decomposition takes place.
Moreover, since the action of acetic anhydride on codeinone makes it possible to isolate 3-methoxy-4:6 dihydroxyphenanthrene,[16] the respective positions of the phenol group and of the alcoholic hydroxyl must clearly be 3 and 6.
http://www.unodc.org/unodc/en/bulletin/bulletin_1950-01-01_2_page004.html

  
 Production of thebaine and oripavine - US Patent 6723894
The enzyme codeinone reductase (NADPH) is believed to be active in both pathways, reducing codeinone to codeine and morphinone to morphine.
Codeinone reductase is the only known enzyme active in both pathways.
Codeinone and morphinone vary only in the presence of a methyl group at the 3-position of codeinone.
http://www.patentstorm.us/patents/6723894.html

  
 Annotated Rhodium Chemistry Archive - Opioid chemistry - Heroin Helper
There is a lot of information on making intermediaries such as the process for changing codeinone to 14-hydroxycodeinone with hydrogen peroxide (H2O2).
This lengthy article presents three procedures for creating oxycodone from codeine.
The second article describes various processes to form 14-Hydroxycodeinone from Codeine via Codeinone.
http://www.heroinhelper.com/curious/chemistry/rhodium.shtml

  
 UNODC - Bulletin on Narcotics - 1958 Issue 3 - 006
Effect of acidity on oxidizing effect of potassium permanganate on codeinone (from thebaine), using Wegner's method for codeine
The reason for this is apparently that with hydrolysis not only codeinone, but also other products appear, as analysis of the hydrolosis products by paper chromatography showed.
For determining the codeine one needs only to heat the sulphuric-acid solution containing both alkaloids before oxidization for some time in a boiling water-bath.
http://www.unodc.org/bulletin/bulletin_1958-01-01_3_page007.html

  
 Morphine Biosynthetic Pathway: Density Of Morphine on The Golden Sites
classifications of morphine to morphine biosynthesis are salutaridinol 7-O-acetyltransferase and codeinone reductase the penultimate enzyme of the morphine pathway top 1 and morphine that reduces.The rate-limiting enzyme in the porphyrin biosynthetic pathway.
His group plans to identify the genes and enzymes behind the human morphine biosynthesis pathway.Specific
http://morphine-biosynthetic-pathway.goldensites.info

  
 From the Cover: The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver ...
of the keto moiety of codeinone to the 6-hydroxyl group of codeine
Codeinone is then reduced in the laticifer into
The combined results of the enzymological and molecular genetic
http://www.pnas.org/cgi/content/full/101/38/13957

  
 Thermoregulated Expression and Characterization of an NAD(P)H-Dependent 2-Cyclohexen-1-one Reductase in the Plant ...
and codeinone to hydromorphone and hydrocodone, respectively (11).
demonstrated with morphinone, codeinone, and neopinone as substrates
http://jb.asm.org/cgi/content/full/181/3/814

  
 Fermentation Biotechnology
It is possible to induce production or enhance production of a compound in cultures by using elicitors, which may be micro-organisms.
Using alginate as the immobilising polymer, digitoxin from Digitalis lanata was converted into digoxin, which is a therapeutic agent in great demand.
Similarly, codeinone was converted into codeine and tyrosine from Mucuna pruriens was converted into DOPA.
http://www.fbae.org/Channels/General_issues/fermentation_biotechnology.htm

  
 [No title]
The synthesis started by an oxidation of codeine (1) to codeinone (2) which underwent ring-opening followed by sceletal rearrangement to give morphothebaine (3) when treated with methanesulfonic acid (Scheme 1).
Deprotection of the catechol moiety will then give the apomorphine.
A similar reaction sequence performed on N-desmethyl codeinone will lead to the labelled target compound.
http://info.dfh.dk/phd/forskningensdag/2004/p25.doc

  
 New Scientist Breaking News - Morphine-free poppies could help fight malaria
This in turn stopped the synthesis of the opiates at the stage at which a compound called reticuline is produced.
A team led by Philip Larkin from CSIRO Plant Industry in Canberra, Australia, used RNA interference (RNAi) to silence - or “turn off” - the genes responsible for producing an enzyme called codeinone reductase.
http://www.newscientist.com/news/news.jsp?id=ns99996667

  
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They are therefore additions to a recently recognized and, as yet, ill-defined class of behaviorally active compounds.
RX 336-M, a new chemical tool in the analysis of the quasi-morphine withdrawal syndrome.
Cowan A. RX 336-M (7,8-dihydro-5',6'-dimethylcyclohex-5'-eno-1',2',8',14 codeinone) and four other chemically-diverse agents--AG-3-5 (1-[2-hydroxyphenyl]-4-[3-nitrophenyl]-1,2,3,6-tetrahydropyrimidine-2-one), Sgd 8473 (alpha-[4-chlorobenzylideneamino)-oxy]-isobutyric acid), thyrotropin releasing hormone (TRH), and sodium valproate--each induce signs of withdrawal, most notably 'wet-dog' shaking, after acute i.p.
http://www.wellstreetpharmacy.com/ref-depakote/depakote-research-abs3.764.html

  
 Plant Tissue Culture: an alternative for production of useful metabolite. Chapter 7.
(153), therefore studied the biotransformation of codeinone to codeine using immobilized cells of P.
The efficient production of thebaine and codeine using cell culture systems by de novo synthesis was not successful, Furuya et al.
The conversion yield was 70.4% and about 88% of codeine converted was excreted into the medium.
http://www.fao.org/docrep/t0831e/t0831e08.htm

  
 μ Receptor
-p-substituted cinnamoylaminomorphinones and their partial mu agonist codeinone relatives.
http://www.komabiotech.co.kr/product/neuro/category/mu_Receptor.htm

  
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This action of the five diverse chemicals appears to be subserved by a common pharmacological component, because pretreatment with d-lysergic acid diethylamide (0.03--1.0 mg kg-1, s.c.) attenuated the shaking behavior in a dose-related manner, and cross tolerance was found between RX336-M and TRH, sodium valproate, and AG-3-5.
Cowan A, Watson T. Thyrotropin-releasing hormone (TRH), sodium valproate, AF-3-5 (1-[2-hydroxyphenyl]-4-[3-nitrophenyl]-1,2,3,6-tetrahydropyrimidine-2-one), RX336-M (7,8-dihydro-5',6'-dimethylcyclohex-5'-eno-1',2',8',14 codeinone), and Sgd 8473 (alpha-[4-chlorobenzylideneamino)-oxy]-isobutyric acid) each induced repetitive shaking of the body of rats after intraperitoneal injection.
Lysergic acid diethylamide antagonizes shaking induced in rats by five chemically different compounds.
http://www.wellstreetpharmacy.com/ref-depakote/depakote-research-abs3.45.html

  
 Enzyme Supplement 1999 EC 1
Comments: stereospecifically catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
Comments: stereospecifically catalyses the reversible reduction of salutaridine to salutaridinol, which is a direct precursor of morphinan alkaloids in the poppy plant.
Lenz, R., Zenk, M.H. Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures.
http://alpha.qmw.ac.uk/~ugca000/iubmb/enzyme/sup98/noGreek/EC1.html

  
 the sunshine project
Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum.
Similarly, German researchers are working (with funds of the German chemical industry) to identify key genes in the morphine synthesis of opium poppy.
http://www.sunshine-project.de/infos/archiv/hintergrund/nr_04.html

  
 Papaver Somniferum -- The Opium Poppy Information Library
United States Patent: 6,008,355: A process is provided for preparing oxycodone from codeine comprising either: (A) the steps of (1) oxidizing codeine so as to form codeinone; (2) converting codeinone to oxycodone in a two-step-one-pot reaction: first reacting codeinone with hydrogen peroxide in water in the presence of an acid at from about 15.degree.
United States Patent: 6,177,567: A method for the preparation of oxycodone, and salts thereof, from codeine comprising oxidation of codeine to codeinone, formation of an dienolsilyl ether congener of codeinone in strong amine base, oxidation of the dienolsilyl ether congener using peracetic acid, and hydrogenation of the resulting 14-hydroxycodeinone product.
http://www.poppies.org/news/archive/arc12.shtml

  
 RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy - Nature Biotechnology
We report on the silencing of codeinone reductase (COR) in the opium poppy, Papaver somniferum, using a chimeric hairpin RNA construct designed to silence all members of the multigene COR family through RNA interference (RNAi).
Correspondence should be addressed to Philip J Larkin philip.larkin@csiro.au
http://www.nature.com/doifinder/10.1038/nbt1033

  
 Barley1 GeneChip Exemplar Details of Barley1_34573
Barley1 exemplars and BEST BLASTX NR results are kindly provided by Dr. Timothy Close from HarvEST:Barley.
BEST TBLASTX ATH1 GeneChip Exemplar: 262903_at, ; atAt1g59950; NADPH-dependent codeinone reductase, putative similar to NADPH-dependent codeinone reductase GI:6478210 from [Papaver somniferum] Length = 963, Expect= 6e-38, match=49/85 aa.
http://www.barleybase.org/barley1contig.php?exemplar=Barley1_34573

  
 In vivo formation of codeinone and morphinone from codeine. Isolation and identification from guinea pig bile -- Ishida ...
Codeinone (CO) and morphinone (MO) were isolated and identified in the bile
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.
http://dmd.aspetjournals.org/cgi/content/abstract/19/5/895

  
 References - chalcone synthase - HORT640 - Metabolic Plant Physiology - Department of Horticulture and Landscape ...
Unterlinner B, Lenz R, Kutchan TM 1999 Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum.
http://www.hort.purdue.edu/rhodcv/hort640c/referen/chalcs.htm

  
 The opium poppy : sites of alkaloid biosynthesis
The localization of laticifers was demonstrated using antibodies specific to the major latex protein (MLP), which is characteristic of the cell type.
The benzylisoquinoline alkaloids of opium poppy accumulate in the cytoplasm, or latex, of specialized laticifers that accompany vascular tissues throughout the plant.
However, immunofluorescence labeling using affinity-purified antibodies showed that three key enzymes, (S)-N-methylcoclaurine 3'-hydroxylase (CYP80B1), berberine bridge enzyme (BBE), and codeinone reductase (COR), involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine, are restricted to the parietal region of sieve elements adjacent or proximal to laticifers.
http://www.opioids.com/opium/alkaloids.html

  
 Addiction: brain mechanisms and their treatment implications
Very long-acting narcotic antagonists: the 14B-p-substituted cinnomoylammomorphinones and their partial mu agonist codeinone relatives.
http://www.drugtext.org/library/articles/nutt01.htm

  
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make you dizzy or drowsy Rising Whooping Cough Incidence Prompts Booster aleve dosage Vaccine } { Alfentanil } { Buprenorphine } { Carfentanil } { Codeine } { Codeinone } Decreasing
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 [No title]
The solvent was then removed from the solution under vacuum until its volume was reduced to 1/leo Codeinone of a clear pure colour was obtained by concentration of the solution, filtration and washing with ethyl ether.
The extract was added to the previous organic phase, washed with water, and dried with anhydrous sodium sulphate.
96 g Codeinone having a melting point of 165-167°C and a purity of 90.36% were obtained with a calculated yield of 98%.
http://uberspace.textfiles.com/uploads/clandestine.txt

  
 EC 1.1.1.247
Lenz, R. and Zenk, M.H. Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures.
Lenz, R. and Zenk, M.H. Stereoselective reduction of codeinone, the penultimate step during morphine biosynthesis in Papaver somniferum.
http://www.chem.qmw.ac.uk/iubmb/enzyme/EC1/1/1/247.html

  
 Enzymes of the biosynthesis of octadecanoid-derived signalling molecules -- Schaller 52 (354): 11 -- Journal of ...
an enzyme which reduces morphinone to hydromorphone or codeinone
http://jexbot.oupjournals.org/cgi/content/full/52/354/11

  
 University of Leicester Biochemistry Department
Together with morphine dehydrogenase, MR catalyses the first step in the degradation of morphine and codeine Both enzymes are potentially useful for the production of semisynthetic opiate drugs.
Morphinone reductase (MR) from Pseudomonas putida M10 catalyses the NADH-dependent saturation of the carbon-carbon double bond of morphinone and codeinone, yielding hydromorphone and hydrocodone, respectively.
http://www.le.ac.uk/biochem/research/nss4_r.html

  
 Biotransformation of Explosives by the Old Yellow Enzyme Family of Flavoproteins -- Williams et al. 70 (6): 3566 -- ...
of the other four enzymes, with only codeinone being a good
http://aem.asm.org/cgi/content/full/70/6/3566

  
 [No title]
fzmb013f008a08k0 10^-13 NADPH-dependent codeinone reductase, putative [Arabidopsis thaliana] 15218958/refNP_176203.1
http://www.danforthcenter.org/maize/data/filtered_annot.txt

  
 E.C.1.1.1.247 Codeinone reductase (NADPH).
Comments: Catalyzes the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
Reaction: Codeine + NADP(+) = codeinone + Nadph.
http://www.biochem.ucl.ac.uk/bsm/enzymes/ec1/ec01/ec01/ec0247/index.html

  
 Mouse protein: Q9JLI0 - Aldo-keto reductase a (Mus musculus 10 day old male pancreas cDNA, RIKEN full-length enriched ...
The alignments can suggest function of a gene.
ref:NP_176204.1 - NADPH-dependent codeinone reductase, putative [Arabidopsis thaliana]
http://marvester.embl.de/marvester/Q9JL/Q9JLI0.htm

  
 A Tale of Three Cell Types: Alkaloid Biosynthesis Is Localized to Sieve Elements in Opium Poppy -- Bird et al. 15 (11): ...
Unterlinner, B., Lenz, R., and Kutchan, T.M. Molecular cloning and functional expression of codeinone reductase: The penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum.
Sites of Action of (S)-N-Methylcoclaurine-3'-Hydroxylase (CYP80B1), Berberine Bridge Enzyme (BBE), and Codeinone Reductase (COR) in the Biosynthesis of Morphine and Sanguinarine.
berberine bridge enzyme (BBE), and codeinone reductase (COR),
http://www.plantcell.org/cgi/content/full/15/11/2626

  
 JNNP -- eLetters for Lopez et al., 75 (7) 1019-1024
Hitosugi N, Hatsukari I, Ohno R, Hashimoto K, Mihara S, Mizukami S, Nakamura S, Sakagami H, Nagasaka H, Matsumoto I, Kawase M. Comparative analysis of apoptosis-inducing activity of codeine and codeinone.
http://jnnp.bmjjournals.com/cgi/eletters/75/7/1019

  
 Erowid Psychoactive Vaults
I wonder if all those methods for reduction of the double bond in hydroxycodeine to get oxycodone are applicable to reduction of codeine or codeinone.
The one about "reduction of the bromination products" sounds like they add bromine across the double bond and then reduce the halide, I believe hydrides (LAH, NaBH4) can be used for this, and maybe H2 + catalyst, but I'm really not too sure.
About hydrocodone: Prepn by hydrogenation of codeinone: Mannich, Lowenheim, _Arch Pharm_ 258, 295 (1920); by oxidation of dihydrocodeine, Ger.
http://www.erowid.org/chemicals/opiates/opiates_info2.shtml

  
 esp@cenet Ansicht [Liste der Familienmitglieder]
Method for the preparation of codeinone from thebaine
Warum werden für ein Dokument verschiedene Veröffentlichungen in ein und demselben Land angezeigt?
http://v3.espacenet.com/family?DB=EPODOC&IDX=GB937128&OREQ=0&F=8&textdoc=TRUE&CY=ep&LG=de

  
 Energy Citations Database (ECD) - Energy and Energy-Related Bibliographic Citations
Energy Citations Database (ECD) Document #6786856 - Biosynthetic conversion of thebaine to codeinone.
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987); ;CODEINONE-- BIOSYNTHESIS;THEBAINE-- CHEMICAL REACTIONS; CARBON 14 COMPOUNDS;CHEMICAL REACTION KINETICS;CODEINE;ISOTOPIC EXCHANGE;LABELLED COMPOUNDS;MORPHINE;OXYGEN 18;PAPAVER SOMNIFERUM;TRACER TECHNIQUES
http://www.osti.gov/energycitations/product.biblio.jsp?osti_id=6786856

  
 Greenplanet.net
In collaborazione con la Tasmanian Alkaloids di Westbury) e la Johnson Johnson Research di Strawberry Hills, sono stati costruiti degli RNAi capaci di 'silenziare' il gene per la reduttasi del codeinone (COR) nei papaveri da oppio.
http://www.greenplanet.net/StampaArticolo6207.html

  
 BLASTX+BEAUTY Search Results
>gi6478204gbAAF13736.1AF108432_1 (AF108432) NADPH-dependent codeinone reductase [Papaver somniferum] Length = 321 Frame -3 hits (HSPs): _____________ __________________________________________________ Database sequence:
>gi6478208gbAAF13738.1AF108434_1 (AF108434) NADPH-dependent codeinone reductase [Papaver somniferum] Length = 321 Frame -3 hits (HSPs): _____________ __________________________________________________ Database sequence:
>gi6478210gbAAF13739.1AF108435_1 (AF108435) NADPH-dependent codeinone reductase [Papaver somniferum] Length = 321 Frame -3 hits (HSPs): _____________ __________________________________________________ Database sequence:
http://psi081.ba.ars.usda.gov/microarray/Blast_deposit/C01B10.seq.blast2x_b.html

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