Amide (e.g., Chloramphenicol, Etc.) Patents (Class 435/129)
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Publication number: 20030157671Abstract: Provided are processes for the synthesis of aniline derivatives, specifically certain aniline derivatives which have activity as thyroid receptor ligands.Type: ApplicationFiled: October 17, 2002Publication date: August 21, 2003Inventors: Ramakrishnan Chidambaram, Joydeep Kant, Raymond E. Weaver, Jurong Yu, Arun Ghosh
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Publication number: 20030157670Abstract: Capsaicin decomposing/synthesizing enzymes are disclosed, which each have the following physical and chemical properties: (1) function and substrate specificity: the enzyme catalyzes a decomposition and/or synthesis reaction of capsaicin and/or capsaicin analogs; (2) an optimal temperature range: near 55° C.; and(3) an optimal pH range of 7-8. Microorganisms to be used for producing these enzymes are also disclosed.Type: ApplicationFiled: July 17, 2002Publication date: August 21, 2003Applicant: OKAYAMA UNIVERSITYInventors: Kazuhiro Nakanishi, Takaharu Sakiyama, Koreyoshi Imamura
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Publication number: 20030148478Abstract: A novel biotechnological process for the preparation of nitriles, starting from amides, is described. Micro-organisms of the genus Amycolatopsis, Actinomadura or Rhodococcus are employed for this process.Type: ApplicationFiled: September 3, 2002Publication date: August 7, 2003Inventors: Karen Tracey Robins, Toru Nagasawa
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Patent number: 6599721Abstract: The invention relates to a novel method for the preparation of optically active 3,3,3-trifluoromethyl-2-alkyl propionic acid derivatives of the general formulae (I) and (II), in which R is ethyl or methyl and X is OH or NH2, provided that if R is methyl X≠—OH. The method comprises the reaction of a racemic propionic acid amide of the general formula (III) either by means of microorganisms which are able to use the propionic acid amide in the form of the racemate or one of its optically active isomers as the only nitrogen source or by means of a polypeptide with amidohydrolase activity which is able to hydrolyze the propionic acid amide. The invention also relates to new optically active representatives of this category of compounds.Type: GrantFiled: August 23, 2001Date of Patent: July 29, 2003Assignee: Lonza AGInventors: Andrew Naughton, Nicholas Shaw
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Publication number: 20030124691Abstract: An objective of the present invention is to provide a method for producing amide compounds.Type: ApplicationFiled: June 13, 2002Publication date: July 3, 2003Applicant: Daicel Chemical Industries, Ltd.Inventors: Tohru Nagasawa, Akinobu Matsuyama
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Publication number: 20030104586Abstract: The invention is to provide a process for effectively removing impurities contained in an amide compound-containing solution by making an amide compound-containing solution, particularly an amide compound-containing solution produced by a hydration reaction of a nitrile compound by using a microorganism fungus body containing nitrile hydratase or a processed product of the microorganism fungus body, in contact with activated carbon under acidic conditions.Type: ApplicationFiled: September 14, 2001Publication date: June 5, 2003Inventors: Takeya Abe, Kiyoshi Itou, Kenju Sasaki, Seiichi Watanabe, Tamotsu Asano
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Patent number: 6569652Abstract: The present invention relates to a process for producing optically active diols represented by the general formula (II): wherein R1 represents (CH2)n, CH═CH, O, S or NH whereupon n is an integer of 1 to 4, and R2 represents hydrogen, C1-6 alkyl, C1-6 alkoxy, (C1-6 alkoxy)-carbonyl, hydroxy, carboxy, halogen, nitro or amino, which comprises treating compounds represented by the general formula (I): wherein R1 and R2 have the same meanings as defined above, with a culture of a microorganism belonging to the genus Rhodococcus, Bacillus, Brevibacterium or Gordona and being capable of stereoselectively diolating a double bond in ring A, or with a culture of Mortierella vinacea, or with said microorganism itself, or with a treated material from said microorganism.Type: GrantFiled: February 25, 2000Date of Patent: May 27, 2003Assignee: Merck & Co., Inc.Inventors: Tamotsu Eguchi, Hideyo Kumazawa, Kenichi Mochida
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Publication number: 20030068789Abstract: In cultivating a microorganism having nitrile hydratase production ability, by allowing at least one of a ketose, such as fructose, and a sugar alcohol, such as mannitol, to be present, growth inhibition by cobalt ion is prevented, thereby achieving cultivation at a high concentration and with a high activity.Type: ApplicationFiled: September 23, 2002Publication date: April 10, 2003Inventors: Koichiro Ryuno, Etsuko Kobayashi
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Publication number: 20030059905Abstract: The present invention provides a purification process whereby deferoxamine B produced by a microorganism and in mixture with other polyhydroxamates produced by the microorganism may be converted into its mesylate salt substantially free of the other polyhydroxamates and substantially free of chloride ion. The process includes adsorption and desorption of the deferoxamine B on an adsorption resin, direct precipitation of the deferoxamine free base out of the eluent from the adsorption resin, contacting of the deferoxamine B free base with methanesulfonic acid and isolation of the deferoxamine B mesylate salt by precipitation. This process minimizes decomposition of deferoxamine B.Type: ApplicationFiled: June 18, 2002Publication date: March 27, 2003Inventors: Vilmos Keri, Zoltan Czovek, Attila Mezo
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Patent number: 6518048Abstract: The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula starting from an isophthalic acid derivative of formula 4,5-Diamino shikimic acid derivatives are potent inhibitors of viral neuraminidase.Type: GrantFiled: March 19, 2001Date of Patent: February 11, 2003Assignee: Hoffmann-La Roche Inc.Inventors: Hans Iding, Beat Wirz, Ulrich Zutter
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Publication number: 20020160466Abstract: The invention is a process for continuously producing an amide compound by reacting a microorganism fungus body containing nitrile hydratase or a processed product of the microorganism fungus body with a nitrile compound in an aqueous medium, characterized in that after contacting said fungus body or said processed product of said fungus body with said nitrile compound in said aqueous medium, a reaction solution thus obtained is further subjected to reaction under conditions having a plug flow region, and according to the invention, an amide compound aqueous solution of a high concentration a high purity can be easily obtained in an extremely high conversion rate of a nitrile compound without a condensation process.Type: ApplicationFiled: November 29, 2001Publication date: October 31, 2002Inventors: Takeya Abe, Kiyoshi Ito, Kenju Sasaki, Seiichi Watanabe, Toshihisa Tachibana, Tamotsu Asano
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Publication number: 20020137153Abstract: Enantioselective or enantiospecific nitrilases and nitrile hydratases are used to produce R or S enantiomers of amides, and carboxylic acids. R-amino acids and S-amino acids are produced using such enantioselective enzymes. In addition, methods of producing and screening enantioselective nitrilases and nitrile hydratases are provided.Type: ApplicationFiled: October 4, 2001Publication date: September 26, 2002Inventors: Sandra W. Ramer, Gjalt Huisman, Jim Millis, Roger Sheldon, Stephen delCardayre, Matthew Tobin, Anthony Cox, S. Christopher Davis
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Patent number: 6444451Abstract: A novel biotechnological process for the preparation of nitriles, starting from amides, is described. Microorganisms of the genus Amycolatopsis, Actinomadura or Rhodococcus are employed for this process.Type: GrantFiled: March 27, 2000Date of Patent: September 3, 2002Assignee: Lonza AGInventors: Karen Tracey Robins, Toru Nagasawa
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Patent number: 6436697Abstract: A process for the preparation of a compound of formula (1) comprises reacting compounds of formulae (2) and (3) in the presence of an enzyme, wherein A is a thiol-protecting group, B, C and D are each the same or different organic groups of up to 30 C atoms, optionally functionalized at any position, provided that neither a primary amine nor a primary amide is present, and X is a group that can be displaced by NH2.Type: GrantFiled: October 22, 1999Date of Patent: August 20, 2002Assignee: Darwin Discovery, Ltd.Inventors: Karen Holt, Stephen John Clifford Taylor, Peter David Tiffin
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Patent number: 6387258Abstract: A process for purifying statin compounds from a fermentation broth by extraction and crystallization is disclosed. A fermentation broth is subjected to a pretreatment procedure which involves an alkaline pretreatment and an alkaline purification. Following the pretreatment procedure, the statin compound is extracted under acidic conditions into a hydrophobic solvent and purified by crystallization. The organic extraction solvent is concentrated and then extracted with a mild base. The statin compound is then purified by crystallization.Type: GrantFiled: January 25, 2001Date of Patent: May 14, 2002Assignee: Biogal Gyogyszergyar Rt.Inventors: Vilmos Keri, Lajos Deak, Iiona Forgacs
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Publication number: 20020042108Abstract: The invention discloses a new method for producing enantiomer-enriched 1-amino-4-(hydroxymethyl)-cyclopent-2-ene derivatives of the general formulae (I) and (II) in which R1 is hydrogen or a possibly substituted C1-8 alkyl rest, aryl rest or cycloalkyl rest and R2 is a possibly substituted acyl. According to said method a racemic 1-amino-4-(hydroxymethyl)-cyclopent-2-ene derivative of general formula (III), in which R1 has the meaning given above, is converted using a hydrolase and in the presence of an acylation agent.Type: ApplicationFiled: June 22, 2001Publication date: April 11, 2002Applicant: LONZA AGInventors: Walter Brieden, Kay-Sara Etter, Michael Petersen
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Publication number: 20020012977Abstract: The following invention relates to a process for oxidizing alkyl groups attached directly or via a linker, to a sulfonamide moiety (II) by the use of cytochrome P450 enzymes, to give the corresponding alcohol or carboxylic acid (I).Type: ApplicationFiled: May 29, 2001Publication date: January 31, 2002Inventor: Michael Stephen Pacey
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Publication number: 20010044141Abstract: The present invention relates to a novel Rhodococcus bacterium and to a process of hydrolyzing a cyano group of a nitrile compound using a novel Rhodococcus bacterium to produce the corresponding carboxylic acid. The present invention also relates to a process of producing carboxylic acids, in particular cyano carboxylic acids using a transformant transformed with a plasmid containing a nitrilase gene, a nitrile hydratase gene and an amidase gene derived from Rhodococcus bacteria capable of exhibiting particularly excellent position selectivity for the cyano group of aromatic polynitrile compounds, to such a transformant, such a plasmid, to such genes, to a process of producing an enzyme using the transformant, and to enzymes obtained by the process. The carboxylic acids, in particular cyano carboxylic acids obtained by the present invention are useful as starting materials for the synthesis of drugs, agrochemicals, dyestuff and other chemicals.Type: ApplicationFiled: February 22, 2001Publication date: November 22, 2001Inventors: Hirobumi Akoi, Harumi Kamachi
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Patent number: 6303350Abstract: The present invention has for its object to provide novel biologically active substances which is of value as a therapeutic agent for fungal infections and immune disorders. This invention is related to a biologically active substance TKR2449 analog(s) which is represented by the following general formula (A); (In the formula, R1, R2 and R3 are the same or differ each other, and each represents hydrogen or an alkyl group of carbon number of 1 to 4. R4 is a linear or branched alkyl or alkenyl group of carbon number of 1 to 8.).Type: GrantFiled: March 7, 2000Date of Patent: October 16, 2001Assignee: Takara Shuzo Co., Ltd.Inventors: Kazutoh Takesako, Mitsuhiro Ueno, Naoyuki Awazu, Yoko Uno, Ikunoshin Kato
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Patent number: 6252112Abstract: A novel process for the preparation of (1S, 4R)- or (1R, 4S)-4-(2-amino-6-chloro-9H-purin-9-yl)-2 -cyclopentene-1-methanol of the formula is described.Type: GrantFiled: August 13, 1999Date of Patent: June 26, 2001Assignee: Lonza A.G.,Inventors: Christine Bernegger, Eva Maria Urban, Olwen Mary Birch, Kurt Burgdorf, Frank Brux, Kay-Sara Etter, Pierre Bossard, Walter Brieden, Laurent Duc, John Gordon, Colm O'Murchu, Yves Guggisberg
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Patent number: 6251625Abstract: The invention concerns a process for the enzymatic preparation of protected di- and oligopeptides and the separation of the protective groups used. The process according to the invention enables peptides to be synthesized simply and economically and the protective group to be separated carefully. The process comprises three reaction steps: 1. Preparation of N-carbamoyl amino acid or N-carbamoyl amino acid derivatives; 2. Formation of the peptide bond between the carbamoyl-protected electrophile and nucelophile; and 3. Separation of the carbamoyl-protective group.Type: GrantFiled: April 3, 1998Date of Patent: June 26, 2001Assignee: Degussa AktiengesellschaftInventors: Andreas Bommarius, Karlheinz Drauz, Uwe Eichhorn, Hans-Dieter Jakubke, Matthias Kottenhahn
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Patent number: 6248571Abstract: A process for the preparation of dihydroxypyrimidine derivatives of the general formula: in which R1 and R2 are identical or different and are a hydrogen atom, aryl group, or a C1-C4-alkyl group or an aryl group, starting from a compound of the general formula: in which R2 has the meaning mentioned above and R3 is —CN or COOR4, in which R4 is a C1-C4-alkyl group.Type: GrantFiled: February 25, 1998Date of Patent: June 19, 2001Assignee: Lonza AGInventors: Beat Schmidt, Andreas Kiener, John McGarrity
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Patent number: 6214592Abstract: The present invention relates to an enzyme with amidase activity, particularly towards substrates of the oligomer type derived from PA 6.Type: GrantFiled: April 3, 1998Date of Patent: April 10, 2001Assignee: Rhone-Poulenc Fibres et Polymeres S.A.Inventors: Joël Crouzet, Olivier Favre-Bulle, Catherine Jourdat, Anne-Marie Le Coq, Dominique Petre
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Patent number: 6194196Abstract: The present invention relates to a microbiological process for preparing sphingolipids, especially, tetraacetylphytosphingosine(TAPS), using novel yeast cell Pichia ciferrii DSCC 7-25 under optimal fermentation conditions. Further, this invention concerns a novel yeast cell Pichia ciferrii DSCC 7-25 and it's isolation method from wild type of Pichia ciferrii strain.Type: GrantFiled: June 11, 1999Date of Patent: February 27, 2001Assignee: Doosan CorporationInventors: Chang Seo Park, Ji Hean Jeong, Sung Yong Hong, Woo Seok Choi
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Patent number: 6184008Abstract: An industrially advantageous production method of an optically active alcohol useful for cosmetics and medical supplies or production intermediates thereof using an esterase having an ability to selectively hydrolyze an optically active sphingoid compound.Type: GrantFiled: June 21, 1999Date of Patent: February 6, 2001Assignee: Sumitomo Chemical Company Ltd.Inventors: Hiromichi Ohta, Takeshi Sugai, Takeshi Ishii, Satoshi Mitsuda
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Patent number: 6174711Abstract: A method for producing L-allysine acetal represented by general formula (II), comprising reacting D,L-allysinamide acetal represented by general formula (I) with cells of microorganism or treated cell product having an activity of stereoselectively hydrolyzing L-allysinamide acetal, wherein R1 and R2, which may be the same or different, each independently represent a lower alkyl group, or R1 and R2 are combined to form an alkylene group represented by [CH2]n, and n is 2 to 3. D,L-allysinamide acetal represented by general formula (I) is also in the scope of the invention. According to the present invention, L-allysine acetal useful as a raw material for medicine can be produced in a smaller number of steps at low costs.Type: GrantFiled: July 12, 1999Date of Patent: January 16, 2001Assignee: Mitsubishi Gas Chemical CompanyInventors: Akinori Tanaka, Masaharu Doya, Takako Uchiyama, Torakazu Tahara
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Patent number: 6153415Abstract: A process for the bioconversion of a nitrile to its corresponding amide product, particularly acrylonitrile to acrylamide which is used for forming polymers. The process uses a thermophilic bacterium having a nitrile hydratase activity that is constitutively expressed, activated by cobalt ions, stable at 60.degree. C., and is most active between 20.degree. C. to 70.degree. C. with optimum activity at 55.degree. C. Alternatively, the process uses the enzyme extracted from the thermophilic bacterium to convert a nitrile to its amide product. The genes encoding nitrile hydratase and amidase are described in which the former is useful for the conversion of an nitrile to its amide and the later is useful for the conversion of an amide to its acid.Type: GrantFiled: February 10, 1999Date of Patent: November 28, 2000Assignee: Board of Trustees operating Michigan State UniversityInventors: Patrick J. Oriel, Rugmini Padmakumar, Sang Hoon Kim
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Patent number: 6133018Abstract: 2-Aminopropane is used as the amine donor in the stereoselective synthesis of a chiral amine from a ketone with a transaminase. In a typical embodiment, (S)-1-methoxy-2-aminopropane is prepared by bringing methoxyacetone into contact with a transaminase in the presence of 2-aminopropane as an amine donor until a substantial amount of methoxyacetone is converted to (S)-1-methoxy-2-aminopropane and 2-aminopropane is converted to acetone. In a second embodiment, L-alanine is prepared by bringing pyruvic acid into contact with a transaminase in the presence of 2-aminopropane as an amine donor.Type: GrantFiled: March 10, 1999Date of Patent: October 17, 2000Assignee: CelgroInventors: Wei Wu, Mohit B. Bhatia, Craig M. Lewis, Wei Lang, Alice L. Wang, George W. Matcham
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Patent number: 6060265Abstract: The present invention describes methods for the detoxification of a mixture of nitrile compounds, or a mixture of nitrile and amide compounds by conversion of the nitrile compound(s) to the corresponding amide or acid compounds using a pure culture of an induced microorganism strain capable of converting a nitrile moiety to an amide or acid moiety. If an amide is formed or is present in the mixture, the amide can be further converted, using the present methods for detoxification, to the corresponding acid. The acid can then, if desired, be further degraded to CO.sub.2, H.sub.2 O and biomass. The induced pure cultures are able to detoxify a mixture of nitriles or a mixture of nitriles and amides which are typically present, in high concentration(s), in nitrile production waste streams.Type: GrantFiled: June 25, 1998Date of Patent: May 9, 2000Assignee: Cytec Technology CorporationInventor: George E. Pierce
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Patent number: 6046043Abstract: The present invention provides a general biocatalyst for transforming saturated carbonyl compounds to their .alpha.,.beta.-unsaturated analogs. The transformation is regio- as well as stereoselective. These catalysts are useful in the chiral resolution of carbonyl compounds as well as in the development of libraries of small molecules to screen as potential drug candidates.Type: GrantFiled: October 28, 1998Date of Patent: April 4, 2000Assignee: The Regents of the University of MichiganInventors: Yerramilli V. S. N. Murthy, Vincent Massey
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Patent number: 6043061Abstract: A process for producing an amide compound is described, wherein from a nitrile compound, the corresponding amide compound is produced by the action of nitrile hydratase, characterized in that the hydrocyanic acid concentration in a composition containing the nitrile compound is reduced by a chemical process, and thereafter nitrile hydratase acts on the nitrile compound. According to the invention, the decrease of the activity of the enzyme nitrile hydratase can be effectively suppressed so that an amide compound can be effectively produced from a nitrile compound.Type: GrantFiled: October 22, 1998Date of Patent: March 28, 2000Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Katsuo Ishii, Kouzo Murao
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Patent number: 6022717Abstract: Process for the oxidation of the oxidizable galactose type of alcohol in oxidizable galactose type of alcohol configuration containing polymer, such as guar, with galactose oxidase in the presence of oxidation promoting chemicals.Type: GrantFiled: December 31, 1997Date of Patent: February 8, 2000Assignee: Hercules IncorporatedInventors: Richard Lee Brady, Raymond Thomas Leibfried, Sr.
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Patent number: 6022718Abstract: A method of producing a capsaicin analogue, comprising reacting a fatty acid having 12 or more carbon atoms or an ester thereof (inclusive of fats and oils) with capsaicin in the presence of lipase to produce an N-vanillyl fatty acid amide having an acyl group containing 12 or more carbon atoms, and a method of producing fats and oils containing capsaicin analogues, comprising reacting edible fats and oils with capsaicin in the presence of lipase to produce N-vanillyl fatty acid amides from a portion of the edible fats and oils are provided. It is possible to produce non-pungent capsaicin analogues and other capsaicin analogues, which facilitates utilization of non-pungent capsaicin analogues in the food industry.Type: GrantFiled: December 21, 1998Date of Patent: February 8, 2000Assignee: Maruzen Pharmaceuticals Co., Ltd.Inventors: Kazuo Iwai, Tatsuo Watanabe, Yukiyoshi Tamura, Susumu Ogawa
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Patent number: 5985627Abstract: A method for transamidating a peptide substrate having a P.sub.1 amino acid residue with a positively charged side chain. According to the invention, carboxypeptidase Y is modified to substitute at least one amino acid having a negatively charged side chain in an S.sub.1 subsite. Additionally, the modified carboxypeptidase Y can include substituted amino acid residues in an S.sub.1 ', S.sub.2 and/or S.sub.3 subsite to accommodate a specific peptide substrate.Type: GrantFiled: February 28, 1997Date of Patent: November 16, 1999Assignee: Carlsberg LaboratoryInventors: Uffe Mortensen, Kjeld Olesen, Henning Stennicke, Steen B. S.o slashed.rensen, Klaus Breddam
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Patent number: 5973203Abstract: A process for preparing acrylic or methacrylic acid amides functionalized with a cationizable tertiary amine, by aminolysis of acrylic or methacrylic acid esters with the aid of enzymes.Type: GrantFiled: December 15, 1997Date of Patent: October 26, 1999Assignee: Coatex S.A.Inventors: Jean-Bernard Egraz, Jean-Marc Suau, Maryvonne Brigodiot-Ignazi, Isabelle Peixoto, Thierry Lalot
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Patent number: 5962284Abstract: Acrylamidase enzymes are provided which have acrylamidase activity at pH 4.0 which is at least 50% of their acrylamidase activity at pH 7.0. Such enzymes can be produced by the novel microorganisms Rhodococcus strains NCIMB 40889 and NCIMB 40755. Such enzymes and microorganisms can be used for reducing free acrylamide in polyacrylamides which are produced at low pH and in particular cationic and substantially non-ionic polyacrylamides.Type: GrantFiled: August 7, 1998Date of Patent: October 5, 1999Assignee: Ciba Specialty Chemicals Water Treatments LimitedInventors: Jonathan Hughes, Yvonne Christine Armitage
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Patent number: 5958742Abstract: The present invention relates to a microbiological process for preparing sphingolipids, especially, tetraacetylphytosphingosine(TAPS), using novel yeast cell Pichia ciferrii DSCC 7-25 under optimal fermentation conditions. Further, this invention concerns a novel yeast cell Pichia ciferrii DSCC 7-25 and it's isolation method from wild type of Pichia ciferrii strain.Type: GrantFiled: July 21, 1998Date of Patent: September 28, 1999Assignee: Doosan CorporationInventors: Chang Seo Park, Ji Hean Jeong, Sung Yong Hong, Woo Seok Choi
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Patent number: 5932454Abstract: The method comprises (1) a carboxylic acid salt providing step comprising permitting a strain of microorganism or a preparation derived from the microorganism to act upon a nitrile to thereby (a) provide at least the corresponding amide which is then hydrolyzed in the presence of a base to provide a salt of the corresponding carboxylic acid or (b) provide a salt of the corresponding carboxylic acid and (2) an electrodialysis step comprising subjecting the carboxylic acid salt provided in the step (1) to electrodialysis to provide the corresponding carboxylic acid and base. Carboxylic acids can be produced without formation of ammonium hydrogen sulfate and other byproducts. The microorganism includes microorganisms of the genera Pantoea and Gordona. The ammonia formed in the step (1) can be reused as a nitrogen source in a nitrile production line.Type: GrantFiled: December 17, 1997Date of Patent: August 3, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuyuki Matsuoka, Akinobu Matsuyama
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Patent number: 5910432Abstract: The present invention provides the amino acid sequence and base sequence of a Pseudonocardia thermophila-derived nitrile hydratase, provides further a method for changing its amino acid sequence and base sequence without substantially changing the functions of said nitrile hydratase, and nitrile hydratases having a base sequence and an amino acid sequence as changed on the basis of said method, and provides furthermore a recombinant plasmid having the gene of said nitrile hydratase, a transformant containing said recombinant plasmid, a method of using said transformant for producing said enzyme, and a method of using said transformant for producing the corresponding amide compound from a nitrile compound.Type: GrantFiled: December 15, 1997Date of Patent: June 8, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Kiyoshi Ito, Toshifumi Yamaki, Teruo Arii, Miyuki Tsuruoka, Takeshi Nakamura
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Patent number: 5900368Abstract: The present invention is directed to an improved process for making PDE IV inhibitors. In specific, this application describes a process for making and purifying a chiral bisaryl alcohol, an intermediate compound necessary for the preparation of PDE IV inhibitors such as CDP 840, by asymmetric bioreduction of a pro-chiral ketone. Furthermore, the bioprocess provides for production of each enantiomer of a bisaryl alcohol at elevated optical purity.This invention takes advantage of a microorganism's ability to reduce a pro-chiral bisaryl ketone to the chiral bisaryl alcohol. The alcohol is readily isolated from the media by solvent extraction, crystallography, or other purification method known to the skilled artisan. The chiral alcohol can then be converted to a PDE IV inhibitor, such as CDP 840, by methods well known in the art.Type: GrantFiled: September 8, 1997Date of Patent: May 4, 1999Assignee: Merck & Co., Inc.Inventors: Michel M. Chartrain, Hywyn R.O. Churchill, Woo-Baeg Choi, Shigeko Yamazaki
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Patent number: 5888785Abstract: The present invention provides a nitrile hydratase nucleic acid fragment isolated from Pseudomonas putida which encodes a nitrile hydratase activity capable of catalyzing the hydrolysis of certain racemic nitrites to the corresponding R- or S-amides. Also provided are transformed microorganisms capable of the active expression of said nitrile hydratase activity. Additionally, the invention provides a transformant harboring the nitrile hydratase gene in conjunction with an amidase gene, both of which may be co-expressed producing active nitrile hydratase and amidase enzymes respectively. Methods for the production of such enantiomeric materials are also provided.Type: GrantFiled: June 24, 1998Date of Patent: March 30, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Robert Donald Fallon, Mark James Nelson, Mark Scott Payne
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Patent number: 5866379Abstract: Enzymes derived from the isolated and substantially purified microorganisms of the present invention, designated herein as strains 52 and 56wt, are capable of hydrating nitriles such as 2-hydroxy-4-(methylthio)-butanenitrile (HMB-nitrile) to their corresponding amides, and further, of hydrolyzing amides such as 2-hydroxy-4-(methylthio)-butaneamide (HMB-amide) to their corresponding carboxylic acids. Advantageously, the nitrile hydratase of these strains is not substantially inhibited by the .alpha.-hydroxybutyramide product being formed; rather, this enzyme maintains the ability to hydrate an .alpha.-hydroxybutyronitrile to its corresponding amide even at high amide concentrations, including at saturating amide conditions. As such, enzymes derived from strains 52 and 56wt are particularly suited for commercial use in preparing agrichemical intermediates such as HMB-amide.Type: GrantFiled: January 28, 1997Date of Patent: February 2, 1999Assignee: Novus InternationalInventors: Richard P. Burlingame, James R. Millis, Fernando Sanchez-Riera, Thomas F. Blackburn, Alan D. Grund
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Patent number: 5858737Abstract: A process is disclosed that bioconverts indene to (1S)-amino-(2R)-indanol substantially free of any of its stereoisomers, by the action of a strain of P. putida or Rhodococcus sp., followed by various chemical step(s), e.g., chiral specific crystallization, treatment with strong acid in the presence of acetonitrile.Type: GrantFiled: August 14, 1996Date of Patent: January 12, 1999Assignee: Merck & Co., Inc.Inventors: Barry C. Buckland, Neal C. Connors, Michel M. Chartrain, Francis P. Gailliot, Randolph L. Greasham, Barbara Jackey, Brian Heimbuch, Chanyong Lee, Roger C. Olewinski, Jr., F. Edward Roberts, Paul J. Reider, Thomas R. Verhoeven, Chris H. Senanayake
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Patent number: 5846792Abstract: Tyrosine decarboxylase, or microorganisms of the genuses Enterococcus, Lactobacillus, Providencia, Fusarium, and Gibberella were reacted with a mixture of the enantiomers of threo-3-phenylserine or its halogen substitution products to produce (R)-2-amino-1-phenylethanol or its halogen substitution products. At the same time, one of the enantiomers of threo-3-phenylserine or its halogen substitution products were selectively left, and optically active threo-3-phenylserine or its halogen substitution products were produced. In addition, a novel material of 3-(3-chlorophenyl)serine, which is a substrate of the reaction in the present invention, was produced. (R)-2-amino-1-phenylethanol or its halogen substitution products, and optically active threo-3-phenylserine or its halogen substitution products can economically be produced on an industrial scale.Type: GrantFiled: April 22, 1997Date of Patent: December 8, 1998Assignee: Daicel Chemical Industries, Ltd.Inventors: Teruyuki Nikaido, Naoki Kawada, Takeshi Hamatani, Yoichiro Ueda
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Patent number: 5827699Abstract: This invention provides a new strain Rhodococcus rhodochrous having a high nitrile hydratase activity and capable of hydrating aliphatic and aromatic nitriles to corresponding amides. An isolated culture of Rhodococcus rhodochrous VKM Ac-1515D is also disclosed for use in the production of nitrile hydratase. An enzymatic inducer is not required in the growth medium, however, the growth medium does include a salt, a carbon source, and a nitrogen source.Type: GrantFiled: August 15, 1995Date of Patent: October 27, 1998Assignee: Gosudarstvenny. Nauchno-Issledovatelsky Institut Genetiki I Selektsii Promshlennykh MikroorganizmovInventors: Alexandr Stepanovich Yanenko, Olga Borisovna Astaurova, Sergei Petrovich Voronin, Tatyana Vasilievna Gerasimova, Nikolai Borisovich Kirsanov, Vladimir Nikolaevich Paukov, Inga Nikolaevna Polyakova, Vladimir Georgievich Debabov
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Patent number: 5789211Abstract: The present invention relates to a gene derived from Pseudomonas chlororaphis B23 strain which encodes a polypeptide having nitrile hydratase activity being capable of hydrating nitriles to amides. The invention also relates to a recombinant DNA containing the gene, and a transformant transformed with the recombinant DNA. The present invention further relates to a method of producing nitrile hydratase using the transformant and of amides using nitrile hydratase.Type: GrantFiled: June 5, 1995Date of Patent: August 4, 1998Assignees: Nitto Chemical Industry Co., Ltd., Teruhiko Beppu, Hideaki YamadaInventors: Hideaki Yamada, Toru Nagasawa, Teruhiko Beppu, Sueharu Horinouch, Makoto Nishiyama
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Patent number: 5763249Abstract: Monoclonal antibodies raised against a 4-nitrophenyl phosphonate hapten catalyze the stereospecific reduction of an .alpha.-ketoamide to the corresponding .alpha.-hydroxyamide in the presence of an appropriate reducing agent.Type: GrantFiled: December 9, 1991Date of Patent: June 9, 1998Assignee: The Regents of the University of CaliforniaInventors: Peter G. Schultz, Mark A. Gallop
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Patent number: 5756306Abstract: A process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide which comprises treating an aldehyde and prussic acid or an .alpha.-hydroxynitrile with a microorganism having nitrilase or nitrile hydratase activity in an aqueous medium and maintaining the aldehyde concentration and/or the .alpha.-hydroxynitrile concentration in the reaction mixture within a predetermined range. Also disclosed is a process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide from an aldehyde and prussic acid with a microorganism in an aqueous medium, which comprises maintaining the cyanogen concentration in the reaction mixture within a predetermined range and supplying the aldehyde to the reaction mixture at a predetermined ratio to the prussic acid.Type: GrantFiled: November 8, 1996Date of Patent: May 26, 1998Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
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Patent number: 5753472Abstract: The present invention has disclosed the amino acid sequence and nucleotide sequence of the .alpha.- and .beta.-subunits of two types of nitrile hydratase derived from Rhodococcus rhodochrous J-1. The DNA fragment encoding nitrile hydratase is inserted into an expression vector and the recombinant vector is used for transformation. The transformant contains multiple copies of the gene and can produce much higher level of nitrile hydratase compared with conventionally used microorganisms.Type: GrantFiled: June 5, 1995Date of Patent: May 19, 1998Assignee: Nitto Chemical Industry Co. Ltd.Inventors: Hideaki Yamada, Toru Nagasawa, Teruhiko Beppu, Sueharu Horinouch, Makoto Nishiyama
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Patent number: H1893Abstract: An enzymatic reduction method, particularly a stereoselective enzymatic reduction method, for the preparation of halohydrins from haloketones. The halohydrin products are particularly useful in the preparation of epoxides, which may be employed as intermediates in the preparation of protease inhibitors such as retroviral protease inhibitors.Type: GrantFiled: July 23, 1996Date of Patent: October 3, 2000Assignee: Bristol-Myers Squibb CompanyInventors: Ramesh N. Patel, Laszlo J. Szarka, Amit Banerjee, Clyde G. McNamee