Preparing Sulfur-containing Organic Compound Patents (Class 435/130)
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Patent number: 7410790Abstract: The yeast which has ?-glutamylcysteine-producing ability and is auxotrophic for pantothenic acid is proliferated in a medium containing a sufficient amount of pantothenic acid, and then it is cultured in a medium containing a limited amount of pantothenic acid to increase the ?-glutamylcysteine content in its cells, whereby the yeast in which ?-glutamylcysteine is accumulated is obtained.Type: GrantFiled: December 11, 2003Date of Patent: August 12, 2008Assignee: Ajinomoto Co., Inc.Inventors: Mariko Suehiro, Hiroaki Nishiuchi, Yasushi Nishimura
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Publication number: 20080146642Abstract: The invention relates to methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid (3APS) in a subject, preferably a human subject. The invention encompasses compounds that will yield or generate 3APS, either in vitro or in vivo. Preferred compounds include amino acid prodrugs of 3APS for use, including but not limited to, the prevention and treatment of Alzheimer's disease.Type: ApplicationFiled: October 12, 2007Publication date: June 19, 2008Inventors: Xianqi Kong, Mohamed Atfani, Benoit Bachand, Abderrahim Bouzide, Stephane Ciblat, Sophie Levesque, David Migneault, Isabelle Valade, Xinfu Wu, Daniel Delorme
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Patent number: 7316918Abstract: An enzymatic process for the preparation of intermediates useful in the synthesis of (?) modafinil.Type: GrantFiled: October 17, 2006Date of Patent: January 8, 2008Assignee: Dipharma S.p.A.Inventors: Sergio Riva, Paola Fassi, Pietro Allegrini, Gabriele Razzetti
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Patent number: 7267974Abstract: Microorganisms showing higher productivity of unusual-polyhydroxyalkanoate (PHA) than ever by using an inexpensive substrate or under specific conditions are obtained from wild strains and mutant strains. The microorganisms are cultured with such substrates to synthesize an unusual-polyhydroxyalkanoate. The unusual-polyhydroxyalkanoate can be produced with high efficiency at low cost.Type: GrantFiled: January 27, 2006Date of Patent: September 11, 2007Assignee: Canon Kabushiki KaishaInventors: Shinya Kozaki, Tsutomu Honma, Tetsuya Yano
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Patent number: 7244620Abstract: The present invention provides a method for quantitatively determining a reducing substance, which comprises reacting a reducing substance in a test specimen with iron (III) ions, reacting iron (II) ions formed by reduction of the iron (III) ions or residual iron (III) ions with a metal indicator which is capable of reacting specifically with the iron (II) ions or the residual iron (III) ions to undergo color development, and carrying out quantitative determination by measuring the degree of color development, wherein a chelating agent which is specific to copper ions is added to the test specimen before the reaction of the reducing substance with the iron (III) ions; and a reagent used for it.Type: GrantFiled: December 24, 2003Date of Patent: July 17, 2007Assignee: Daiichi Pure Chemicals Co., Ltd.Inventors: Masahiro Sekiguchi, Takuji Matsumoto, Hiroyuki Ebinuma
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Patent number: 7229803Abstract: The invention relates to methods for reacting (di)amines as substrates in the presence of a lysine oxidase arid a reducing agent, resulting in alcohols, diols or cyclic secondary amines. In a particular embodiment, the invention is directed to methods of preparing cyclic secondary amines suitable for ultimately synthesizing piperidine-2-carboxylic acid and proline derivatives, useful, for example as thrombin inhibitors.Type: GrantFiled: April 8, 2002Date of Patent: June 12, 2007Assignee: BASF AktiengesellschaftInventors: Thomas Friedrich, Norbert Zimmermann, Rainer Stürmer
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Patent number: 7208631Abstract: A process for producing a 2-alkylcysteinamide, which comprises hydrolysis of a 4-alkylthiazolidine-4-carboxamide represented by the general formula (2) or a salt thereof: wherein R represents a lower alkyl group having 1–4 carbon atoms; and each of R1 and R2 independently represents hydrogen or a lower alkyl group having 1–4 carbon atoms, or R1 and R2 are linked together to form an alicyclic, structure having 4–7 carbon atoms, excluding the case where both R1 and R2 are hydrogen, to give a 2-alkylcysteinamide represented by the general formula (1) or a salt thereof wherein R represents a lower alkyl group having 1–4 carbon atoms. Cells of a microorganism or treated products thereof having activity of stereoselective hydrolysis of a 2-alkyl-L-cysteinamide are allowed to act on the compound represented by the general formula (1) to yield a 2-alkyl-L-cysteine.Type: GrantFiled: April 7, 2004Date of Patent: April 24, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yasushi Higuchi, Akinori Tanaka, Ryuji Hasemi
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Patent number: 7157253Abstract: The invention relates to a method for the production of (R)- or (S)-8-chloro-6-hydroxyoctanoic acid alkyl esters of the general formula (R)-II or (S)-II in which R has the meaning C1-4-alkyl, from 8-chloro-6-oxooctanoic acid alkyl esters of the general formula I in which R has the above meaning, by enzymatic reduction using alcohol dehydrogenases, such as Lactobacillus brevis or Thermoanaerobium brokii, in the presence of cofactor regeneration systems. The resulting (R)- and (S)-8-chloro-6-hydroxyoctanoic acid esters can be converted in a known manner into (R)-?-lipoic acid and (S)-?-lipoic acid, respectively.Type: GrantFiled: October 14, 2002Date of Patent: January 2, 2007Assignee: Viatris GmbH & Co. KGInventors: Michael Müller, Wolfgang Sauer, Gunter Laban
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Patent number: 7135328Abstract: The invention relates to a process for the production of (R)- or (S)-8-chloro-6-hydroxyoctanoic acid alkyl esters of the general formula (R)-II or (S)-II, in which R means C1-4 alkyl, from 8-chloro-6-oxo-octanoic acid alkyl esters of the general formula I, in which R has the above meaning. The desired enantiomers are produced biocatalytically in an enantioselective reduction, wherein as desired the strains Mucor racemosus are used for (S)-II compounds and Geotrichum candidum for (R)-II compounds. The resultant esters may, in known manner, be converted stereospecifically into (R)-?-lipoic acid.Type: GrantFiled: July 20, 2001Date of Patent: November 14, 2006Assignee: Viatris GmbH & Co. KGInventors: Matthias Olbrich, Rainer Gewald
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Patent number: 7094580Abstract: A method of perlecan isolation (from the EHS tumor) which produces “clean” (i.e. substantially “pure”) perlecan is disclosed. Clean perlecan is thus produced in sufficient quantities for use in a number of different in vitro and in vivo assays. In addition, this isolation method exploits a newly discovered aggregating property of a ˜220 kDa heparan sulfate proteoglycan (HSPG) observed during gel filtration chromatography, which allows it to be effectively separated from non-aggregating perlecan. The method employs specific cation exchange, anion exchange, molecular sieve chromatography and immobilized GAG affinity chromatography. It is demonstrated that there are no other contaminating proteins in the perlecan and HSPG preparations, and that the perlecan core protein is intact. Improved, clean perlecan based, rodent models of fibrillar amyloid protein deposition, accumulation and/or persistence in tissues are disclosed.Type: GrantFiled: December 18, 2002Date of Patent: August 22, 2006Assignee: University of WashingtonInventors: Gerardo Castillo, Alan D. Snow
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Patent number: 7056708Abstract: The present invention provides a method of effectively producing polyhydroxyalkanoate having an aromatic substituted residue in its monomer unit. In the method of producing polyhydroxyalkanoate by using microorganisms, microorganisms capable of producing polyhydroxyalkanoate are cultured in a culture medium containing at least one starting compound selected from the group consisting of substituted alkanes represented by formula (1) to produce polyhydroxyalkanoate having, in its molecule, at least one unit selected from the group consisting of 3-hydroxy-substituted alkanoate units represented by formula (2): R—(CH2)n—CH2—CH2—CH3??(1) wherein R represents a residue containing a substituted aromatic ring, and n represents any integer of 1 to 8; wherein R represents a residue containing a substituted aromatic ring, and n represents any integer of 1 to 8. In formulas (1) and (2), a residue R is as described in the specification.Type: GrantFiled: April 10, 2003Date of Patent: June 6, 2006Assignee: Canon Kabushiki KaishaInventors: Takashi Kenmoku, Etsuko Sugawa, Tetsuya Yano, Takeshi Imamura, Tsutomu Honma
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Patent number: 7056540Abstract: The present invention relates to an enzymatic process for the preparation of optically active chiral alcohols using tuberous root Daucus carota; particularly invention relates to an enzymatic process for the preparation of optically active alcohols by enantioselective reduction of corresponding ketones using tuberous root Daucus carota.Type: GrantFiled: October 29, 2002Date of Patent: June 6, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Jhillu Singh Yadav, Samik Nanda, Polepally Thirupathi Reddy, Adari Bhaskar Rao
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Patent number: 7052704Abstract: Fatty acid derivatives of sulfhydryl-containing compounds (for example, sulfhydryl-containing peptides or proteins) comprising fatty acid-conjugated products with a disulfide linkage are employed for delivery of the compounds to mammalian cells. This modification markedly increases the absorption of the compounds by mammalian cells relative to the rate of absorption of the unconjugated compounds, as well as prolonging blood and tissue retention of the compounds. Moreover, the disulfide linkage in the conjugate is quite labile in the cells and thus facilitates intracellular release of the intact compounds from the fatty acid moieties.Type: GrantFiled: May 1, 2001Date of Patent: May 30, 2006Assignee: University of Southern CaliforniaInventors: Wei-Chiang Shen, Hossein M. Ekrami
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Patent number: 7045321Abstract: A polyhydroxyalkanoate characterized by having in the molecule a unit represented by Chemical Formula (1): wherein n may assume any one integral value within the range of from 1 to 8. Also disclosed are a process for producing the polyhydroxyalkanoate by the use of a microorganism having the ability to produce the polyhydroxyalkanoate and accumulate it in the bacterial body; a charge control agent, a toner binder and a toner which contain this polyhydroxyalkanoate; and an image-forming method and an image-forming apparatus which make use of the toner.Type: GrantFiled: February 28, 2002Date of Patent: May 16, 2006Assignee: Canon Kabushiki KaishaInventors: Takeshi Imamura, Etsuko Sugawa, Tetsuya Yano, Tsuyoshi Nomoto, Tomohiro Suzuki, Tsutomu Honma, Takashi Kenmoku, Tatsuki Fukui
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Patent number: 7026143Abstract: Provided is a method of resolving a racemic mixture of a compound of formula I to obtain a desired enantiomer: wherein Ar is C6 or C10 aromatic group that can be substituted with H, C1 to C6 alkyl, trifluoromethyl or halo, R5 is halo or —S—R1, wherein R1 is H or acetyl, and R2 is H or C1 to C6 alkyl, the method comprising: reacting a compound of formula I wherein the compound is an ester whereby R2 is C1 to C6 alkyl with a lipase derived from Mucor meihei to stereoselectively hydrolyze the ester bond to produce an acid; and isolating the acid, wherein the reaction is conducted in a solvent comprising 80% to 98% v/v % organic phase and a residue of water phase (which can be buffered).Type: GrantFiled: July 23, 2003Date of Patent: April 11, 2006Assignee: Bristol-Myers Squibb CompanyInventors: Jingyang Zhu, Li You, Brenda J. White, Shannon X. Zha, Paul M. Skonezny
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Patent number: 6969613Abstract: The present invention provides a method for quantitatively determining hydrogen sulfide or sulfide ions conveniently with high sensitivity, which comprises adding to a sample containing hydrogen sulfide or sulfide ions, metal ions or a compound which liberates said metal ions and a metal indicator which reacts with the metal ions and resultingly undergoes color development, wherein the color development is accelerated or inhibited by the hydrogen sulfide or sulfide ions; and measuring the degree of color development of the metal indicator.Type: GrantFiled: December 7, 1999Date of Patent: November 29, 2005Assignee: Daiichi Pure Chemicals Co., Ltd.Inventors: Hiroyuki Ebinuma, Koji Ushizawa
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Patent number: 6951745Abstract: A method for manufacturing polyhydroxyalkanoate-containing structure, at least a part of a base material surface of the structure being coated with polyhydroxyalkanoate, the method comprises the steps of immobilizing a polyhydroxyalkanoate synthase on the base material surface, synthesizing, on the base material surface, polyhydroxyalkanoate using a 3-hydroxyacyl coenzyme A to become the substrate of the synthase and the synthase and coating at least a part of the base material surface with the synthesized polyhydroxyalkanoate, wherein the synthase contains an amino acid sequence capable of binding to the base material.Type: GrantFiled: July 10, 2002Date of Patent: October 4, 2005Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Nomoto, Tetsuya Yano, Shinya Kozaki, Tsutomu Honma
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Patent number: 6924129Abstract: A method for enzymatically synthesizing a polymer by combining a preselected quantity of an enzyme, a first reactant selected from polymers with at least one carboxylic acid pendant group, a second reactant selected from alcohols, i.e., polyols, in a reaction vessel; heating the reaction vessel to a preselected temperature; and maintaining the reaction vessel at the preselected temperature for a preselected time with mixing, wherein an esterification reaction results at at least one carboxylic acid pendant group of the polymer with one hydroxyl group from the polyol and results in a modified polymer.Type: GrantFiled: October 23, 2002Date of Patent: August 2, 2005Assignee: Polytechnic UniversityInventors: Riahcrd A. Gross, Bishwabhusan Sahoo
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Patent number: 6869782Abstract: A polyhydroxyalkanoate that comprises a unit represented by the following chemical formula (1): wherein x is an integer of 1 to 8 being the same or different in the polyhydroxyalkanoate. The microbial production process is also disclosed.Type: GrantFiled: July 3, 2002Date of Patent: March 22, 2005Assignee: Canon Kabushiki KaishaInventors: Takashi Kenmoku, Etsuko Sugawa, Tetsuya Yano, Takeshi Imamura
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Patent number: 6855472Abstract: The invention is to provide polyhydroxyalkanoate of a novel structure enabling application to wider fields, and a producing method therefor. The invention also provides a biodegradable charge control agent having excellent charging characteristics, excellent dispersibility in the toner resin and improved spent property. The polyhydroxyalkanoate of the present invention is featured by including, in the polymer molecule, a units represented by the general formulas (1) and (2) and at least one of the units represented by the general formulas (3) to (6).Type: GrantFiled: April 29, 2002Date of Patent: February 15, 2005Assignee: Canon Kabushiki KaishaInventors: Takeshi Imamura, Etsuko Sugawa, Tetsuya Yano, Takashi Kenmoku
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Publication number: 20040247711Abstract: There is disclosed a method for preparing allicin which comprises the following steps: (a) mechanically treating a natural source of alliinase to release alliinase therefrom; (b) contacting the mechanically treated alliinase source with an aqueous solution of alliin containing alliin at a concentration greater than that found in raw garlic, whereby the alliin is enzymatically converted to allicin by the alliinase released from the alliinase source: and optionally (c) extracting the resultant allicin into a low boiling point non-polar organic solvent.Type: ApplicationFiled: June 21, 2004Publication date: December 9, 2004Inventors: David Michael Williams, Chandra Mohan Pant
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Patent number: 6808854Abstract: The present invention provides a novel polyhydroxyalkanoate (PHA) containing a 3-hydroxyalkanoic unit which has at its side chain terminal a substituted phenylsulfinyl group and/or a substituted phenylsulfonyl group, and a production process thereof. The novel PHA can be produced by oxidizing with a peroxide a biosynthetic PHA containing a 3-hydroxyalkanoic unit which has at its side chain terminal a substituted phenylsufanyl group. The novel PHA has a superior function as a charge control agent, besides is biodegradable, hence is contributable to environmental conservation.Type: GrantFiled: April 29, 2002Date of Patent: October 26, 2004Assignee: Canon Kabushiki KaishaInventors: Takeshi Imamura, Etsuko Sugawa, Tetsuya Yano, Takashi Kenmoku
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Patent number: 6777153Abstract: A polyhydroxyalkanoate characterized by having in the molecule a unit represented by Chemical Formula (1): wherein n may assume any one integral value within the range of from 1 to 8. Also disclosed are a process for producing the polyhydroxyalkanoate by the use of a microorganism having the ability to produce the polyhydroxyalkanoate and accumulate it in the bacterial body; a charge control agent, a toner binder and a toner which contain this polyhydroxyalkanoate; and an image-forming method and an image-forming apparatus which make use of the toner.Type: GrantFiled: March 26, 2002Date of Patent: August 17, 2004Assignee: Canon Kabushiki KaishaInventors: Tetsuya Yano, Etsuko Sugawa, Takeshi Imamura, Tsutomu Honma, Takashi Kenmoku
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Patent number: 6777224Abstract: The present invention provides a method for enzymatically producing optically active mandelic acid derivatives. An optically active mandelic acid derivative (shown as Formula II) is produced by reacting a culture or cell body of a microorganism, or processed products thereof, with a phenylglyoxylic acid derivative, and then recovering the obtained optically active mandelic acid derivative, wherein the microorganism has the ability to stereo-selectively reduce the phenylglyoxylic acid derivative. An optically active mandelic acid obtained according to the present invention is useful as an intermediate for the synthesis of pharmaceuticals and agricultural chemicals.Type: GrantFiled: October 23, 2002Date of Patent: August 17, 2004Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuya Mitsuhashi, Hiroaki Yamamoto
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Patent number: 6743608Abstract: The present invention relates to a process comprising hydrolysis or trans esterification of one of the two enantiomeric forms of a racemic or enantiomerically enriched ester of formula I or IV by a higher rate than the other by an enzyme to give an ester and a acid (III) or two different esters (V) and (VI) with different R groups both with increased enantiomeric purity and a esterification process of a racemic or enantiomerically enriched acid (VII) by an enzyme to give an ester and an acid both with increased enantiomeric purity.Type: GrantFiled: April 24, 2002Date of Patent: June 1, 2004Assignee: Novo Nordisk Pharmaceuticals, Inc.Inventors: Soren Ebdrup, Heinz-Josef W. Deussen, Magali Zundel
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Patent number: 6737256Abstract: A method is disclosed for the increased production of biotin and the biotin precursor dethiobiotin using a bacterium that produces a lysine-utilizing DAPA aminotransferase. This method involves the use of a bacterium that is either grown in the presence of lysine or deregulated for lysine biosynthesis.Type: GrantFiled: July 14, 1997Date of Patent: May 18, 2004Assignee: Roche Vitamins Inc.Inventors: Scott W. Van Arsdell, R. Rogers Yocum, John B. Perkins, Janice G. Pero
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Patent number: 6689588Abstract: Immobilized garlic alliinase wherein the alliinase is chemically, physically or biologically immobilized, is useful in a method for continuous production of allicin. The method comprises adding a solution of alliin as substrate to a column containing the immobilized garlic alliinase and collecting pure allicin in the effluent. The pure allicin is intended for use as food additive or for the preparation of pharmaceutical compositions for the treatment of viral, bacterial, fungal and parasitic infections, high levels of cholesterol and blood lipids, high blood pressure and thrombosis.Type: GrantFiled: September 12, 2000Date of Patent: February 10, 2004Assignee: Yeda Research and Development Co. Ltd.Inventors: David Mirelman, Meir Wilchek, Talia Miron, Aharon Rabinkov, Hephzibah Sivaraman
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Patent number: 6686439Abstract: PHA containing a novel 3-hydroxy-thioalkanoic acid unit having a highly reactive thienyl group in a side chain thereof, and a method of producing the same are provided. Specifically, 5-(2-thienyl-sulfanyl)valeric acid represented by Chemical Formula [4] below and 6-(2-thienylsulfanyl)hexanoic acid represented by Chemical Formula [5] below are provided. Further, a method of producing PHA, comprising the step of collecting PHA from cells of a microorganism cultured in a medium containing the valeric acid or hexanoic acid, and a novel PHA represented by Chemical Formula [1] below are provided.Type: GrantFiled: February 28, 2002Date of Patent: February 3, 2004Assignee: Canon Kabushiki KaishaInventors: Takashi Kenmoku, Etsuko Sugawa, Tetsuya Yano, Tsuyoshi Nomoto, Takeshi Imamura, Tomohiro Suzuki, Tsutomu Honma
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Patent number: 6627416Abstract: The invention relates to 5′-modified nucleotides and to nucleic acids which contain these nucleotides. Processes for incorporating the 5′-modified nucleotides into nucleic acids, and the subsequent site-specific cleavage of the nucleic acids at the 5′-modified monomer building blocks, are also disclosed. These processes can be employed for nucleic acid sequencing, for generating nucleic acid libraries, for detecting mutations, for preparing support-bound nucleic acids and for pharmaceutical purposes.Type: GrantFiled: January 10, 2001Date of Patent: September 30, 2003Assignee: Europaisches Laboratorium fur Molekularbiologie (EMBL)Inventors: Konrad Faulstich, Wilhelm Ansorge
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Patent number: 6620600Abstract: Provided is a method of resolving a racemic mixture of a compound of formula I to obtain a desired enantiomer: wherein Ar is C6 or C10 aromatic group that can be substituted with H, C1 to C6 alkyl, trifluoromethyl or halo, R5 is halo or —S—R1, wherein R1 is H or acetyl, and R2 is H or C1 to C6 alkyl, the method comprising: reacting a compound of formula I wherein the compound is an ester whereby R2 is C1 to C6 alkyl with a lipase derived from Mucor meihei to stereoselectively hydrolyze the ester bond to produce an acid; and isolating the acid, wherein the reaction is conducted in a solvent comprising 80% to 98% v/v % organic phase and a residue of water phase (which can be buffered).Type: GrantFiled: September 5, 2001Date of Patent: September 16, 2003Assignee: Bristol-Myers Squibb Co.Inventors: Jingyang Zhu, Li You, Brenda J. White, Shannon X. Zhao, Paul M. Skonezny
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Publication number: 20030109015Abstract: A polyhydroxyalkanoate that comprises a unit represented by the following chemical formula (1): 1Type: ApplicationFiled: July 3, 2002Publication date: June 12, 2003Inventors: Takashi Kenmoku, Etsuko Sugawa, Tetsuya Yano, Takeshi Imamura
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Publication number: 20030092140Abstract: Facile methods for preparing diketide and triketide thioesters are disclosed. The resulting thioesters may be used as intermediates in the synthesis of desired polyketides, and may contain functional groups which ultimately reside in side chains on the resulting polyketide and thus can be used further to manipulate the polyketide so as form derivatives. The polyketides produced may also be tailored by glycosylation, hydroxylation and the like. New polyketides and their derivatives and tailored forms are thereby produced.Type: ApplicationFiled: August 8, 2002Publication date: May 15, 2003Inventors: Gary Ashley, Isaac C. Chan-Kai, Mark A. Burlingame
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Patent number: 6524839Abstract: Treatment of cells with lower alcohol provides cells having the reaction rate 350 to 600 times higher than that of cells that are not treated with lower alcohol More specifically, a simple operation of treating cells with lower alcohol provides a catalyst that has a higher activity that that of a cell extract and can be recycled.Type: GrantFiled: March 12, 2001Date of Patent: February 25, 2003Assignee: Kansai Chemical Engineering Co., Ltd.Inventors: Hideki Fukuda, Akihiko Kondo
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Patent number: 6495152Abstract: A class of biopolymer including sulfur in the form of a thioester in the polymer backbone or a thioether in the polymer side chains has been developed. These are preferably produced by fermentation of bacteria with appropriate sulfur containing substrates, which are incorporated by a broad spectrum polyhydroxyalkanoate (“PHA”) polymerase. The sulfur-containing PHAs allow various applications and uses in industry. Representative embodiments of the applications of the sulfur-containing PHAs include their uses in the packaging industry, medicine, pharmacy, agriculture or food industry, as active agents or as coatings, packaging, or carriers.Type: GrantFiled: August 17, 2001Date of Patent: December 17, 2002Assignees: Tepha, Inc., Metabolix, Inc.Inventors: Alexander Steinbuchel, Tina Lütke-Eversloh, Christian Ewering
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Patent number: 6479621Abstract: Microorganisms capable of synthesizing novel polyhydroxyalkanoate having 3-hydroxythienylalkanoic acid as monomer unit, using thienylalkanoic acid as a stock are cultured on a culture medium containing thienylalkanoic acid, and the polyhydroxyalkanoate produced in the cultured cell is extracted andType: GrantFiled: February 28, 2001Date of Patent: November 12, 2002Assignee: Canon Kabushiki KaishaInventors: Tsutomu Honma, Tetsuya Yano, Shin Kobayashi, Takeshi Imamura, Takashi Kenmoku, Shinya Kozaki
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Patent number: 6444450Abstract: A process for large-scale, low cost, batch or continuous production of polyphenols using enzyme-mediated reactions and methods for recycling non-consumed reactants.Type: GrantFiled: January 28, 1998Date of Patent: September 3, 2002Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Joseph A. Akkara, Madhu S. R. Ayyagari, David L. Kaplan
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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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Patent number: 6379935Abstract: A method of producing an &agr;-halo-&agr;,&bgr;-saturated carbonyl compound from an &agr;-halocarbonyl compound having an &agr;, &bgr;-carbon-carbon double bond by reducing said &agr;,&bgr;-carbon-carbon double bond using a microorganism belonging to any one of the genera Acetobacter, Actinomyces, Acinetobacter, Agrobacterium, Aeromonas, Alcaligenes, Arthrobacter, Azotobacter, Bacillus, Brevibacterium, Burkholderia, Cellulomonas, Corynebacterium, Enterobacter, Enterococcus, Escherichia, Flavobacterium, Gluconobacter, Halobacteium, Halococccus, Klebsiella, Lactobacillus, Microbacterium, Micrococcus, Micropolyspora, Mycobacterium, Nocardia, Pseudomonas, Pseudonocardia, Rhodococcus, Rhodobacter, Serratia, Staphylococcus, Streptococcus and Streptomyces, Xanthomonas, or a microbial product thereof. Pseudomonas sp. SD810, SD811 and SD812, Burkholderia sp.Type: GrantFiled: August 5, 1999Date of Patent: April 30, 2002Assignee: Showa Denko Kabushiki KaishaInventors: Harumi Kamachi, Tadashi Yoneda, Motoaki Kamachi, Nobuyoshi Esaki
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Patent number: 6300106Abstract: A method of producing (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methane sulfonate using 1,3-butadiene and a ketoethanal to form an intermediate racemic mixture. The racemic mixture is resolved to remove one isomer from the reaction product mixture. Following resolution, the following steps are performed: reduce the isomer to an alcohol, react the alcohol with triphenylmethyl chloride, ozonalyze the resulting reaction product, reduce the ozonalyzed product to yield a diol and react the diol with a methane sulfonyl compound to form (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methane sulfonate. Alternatively, the racemic mixture may first be reduced and the resulting racemic alcohol mixture is resolved to isolate one isomer of the alcohol and the remaining process steps are followed.Type: GrantFiled: November 22, 2000Date of Patent: October 9, 2001Assignee: PPG Industries Ohio, Inc.Inventor: Jean-Claude Caille
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Patent number: 6277609Abstract: The pesent invention is directed to biotin-producing recombinant cells transformed with an Escherichia coli bioE gene or a functional equivalent thereof, either alone or in combination with at least one additional nucleic acid sequence selected from Bacillus sphaericus bioA, bioB, bioD, bioF, bioW, bioX, and bioY genes, or a functional equivalent of any of these genes. Preferred recombinant cells are capable of converting essentially all biotin vitamers to true biotin. The present invention also provides a method to produce biotin by culturing such recombinant cells under appropriate conditions in an effective medium, which preferably includes biotin precursor supplements.Type: GrantFiled: January 6, 1993Date of Patent: August 21, 2001Assignee: BASF AktiengesellschaftInventor: Christina K. Eddy
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Patent number: 6255088Abstract: Enzymatic sulfations of biomolecules catalyzed by 3′-phosphoadenosine-5′-phosphosulfate (PAPS) dependent sulfotransferases are enhanced by coupling the sulfation reaction an enzymatic regeneration of PAPS. The PAPS is enzymatically regenerated from its hydrolysis product 3′,5′-diphosphate (PAP) using recombinant aryl sulfotransferase as the catalyst and aryl sulfate as the substrate. Biomolecules capable of enhanced sulfation by this method include carbohydrates, oligosaccharides, peptides, proteins, flavonoids, and steroids. When enzymatic sulfation and substrate regeneration steps are coupled, the desulfated aryl group produced in the regeneration step has a spectroscopic signature that can be employed for monitoring the progress of the sulfation of the biomolecule.Type: GrantFiled: September 10, 1999Date of Patent: July 3, 2001Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Michael D. Burkart
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Patent number: 6248573Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) wherein R1 and R2 represent a lower alkyl group, etc., or R1 and R2 may form together an alkylene group, etc.; R3, R4 and R5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.Type: GrantFiled: December 10, 1998Date of Patent: June 19, 2001Assignee: Daicel Chemical Industries, Ltd.Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
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Patent number: 6224864Abstract: Antibiotic 10381a1, wherein R is hydrogen, is a cytosine-containing antibiotic producible by culturing the novel microorganism Streptomyces arginensis in an aqueous medium and isolation thereof. Derivatives wherein R is a C1 to C3 alkyl ester of antibiotic 10381a1, are also disclosed along with the pharmaceutically acceptable salts of both the native and esterified forms. Antibiotic 10381a1 inhibits the growth of selected species of yeast, fungi and bacteria. This invention also relates to a novel process for the preparation of the antibiotics 10381b and to a method of using antibiotics 10381b to promote growth in meat-producing animals. These antibiotics are also obtained by the fermentation of a nutrient medium with the novel microorganism Streptomyces arginensis and are active against selected species of bacteria.Type: GrantFiled: August 10, 1999Date of Patent: May 1, 2001Assignee: Pharmacia & Upjohn CompanyInventors: Alexander D. Argoudelis, Franklin B. Shilliday, Alice L. Laborde, Scott E. Truesdell, Oldrich K. Sebek
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Patent number: 6221637Abstract: Xanthene compounds represented by the formula: wherein R1 is a carboxyl group which may be esterified or amidated; R2 is a hydrogen atom, a hydroxyl group, or a hydrocarbon group which may be substituted; R3 and R4 are the same or different and are a hydroxyl group which may be substituted; R5 and R6 are a hydrogen atom or a halogen atom; R7 is a hydrogen atom, a nitro group, a halogen atom, a hydrocarbon group which may be substituted, a heterocyclic group which may be substituted, or an acyl group which may be substituted; n is an integer of 0 to 2; and Y is an oxygen atom or two hydrogen atoms; and when n is 0, R2 may be a group represented by the formula: wherein the symbols have the same meanings as defined above, or a salt thereof inhibit a binding of B7-1 to CD28, prevent the B7-1-dependent activation of T cells and inhibit IL-2 production from T cells, thus being used as an immunomodulator such as a graft rejection inhibitor or a pharmaceutical composition for theraType: GrantFiled: March 4, 1997Date of Patent: April 24, 2001Assignee: Takeda Chemical Industries, Ltd.Inventors: Tsuneaki Hida, Masahiko Hattori, Tsutomu Kurokawa, Atsushi Nakanishi
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Patent number: 6071738Abstract: The present invention relates to a method for the desulfurization of a fossil fuel containing one or more organosulfur compounds. In one embodiment, the method comprises the steps of (1) contacting the fossil fuel with a biocatalyst capable of converting the organosulfur compound to an oxyorganosulfur compound which is separable from the fossil fuel; and (2) separating the oxyorganosulfur compound from the fossil fuel. The oxyorganosulfur compound can then be isolated, discarded or further processed, for example, via desulfurization by a biocatalyzed process or an abiotic process, such as hydrodesulfurization.Type: GrantFiled: September 19, 1997Date of Patent: June 6, 2000Assignee: Energy BioSystems CorporationInventors: Steven W. Johnson, Daniel J. Monticello, Charles Hazan, Jean-Michel Colin
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Patent number: 6015808Abstract: Pharmaceutical compositions with heretofore unknown and enhanced physical, chemical, and biological properties are prepared by combining known biologically active parent compounds with oxo thia azabicyclo compounds, such as lactam and .beta.-lactam compounds, capable of rapidly transporting the parent compounds in undegraded form to their target sites of action. A process for combining the parent compound with .beta.-lactam compounds consists of dissolving the parent compound in a polar solvent, adding a .beta.-lactam compound, incubating the resulting mixture, followed by drying, and subjecting the remaining solid material to solvent washing or extraction to further purify the new pharmaceutical composition. The new pharmaceutical composition possesses the biological and therapeutic activity of the parent compound and the barrier penetrating characteristics of the .beta.Type: GrantFiled: August 22, 1995Date of Patent: January 18, 2000Inventors: Mandayam Jeersannidhi Thirumalachar, Mandayam Jeersannidhi Narasimhan, Jr.
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Patent number: 6013829Abstract: Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl-3-phenylpropanoic acid of formula (I): characterized in that it comprises the steps consisting in:a) preparing the diol (VI) by reduction of a malonic ester (V) in the presence of a hydride;b) preparing the monoacetates (VII R) or (VII S) respectively;c) subjecting these monoacetates to an oxidation in order to form the acids (IX S) or (IX R);d) saponifying the compounds (IX S) or (IX R) in order to form the hydroxy acids (X S) or (X R);e) thioacylating the hydroxy acids (X S) or (X R) with a mercapto acid R.sub.1 SH (XI), according to a Mitsunobu-type reaction, in order to lead to the desired acids (I R) (I S) respectively and application to the synthesis of N-(mercaptoacyl)amino acid derivatives (II).Type: GrantFiled: November 26, 1997Date of Patent: January 11, 2000Assignee: Societe Civile BioprojetInventors: Denis Danvy, Thierry Monteil, Pierre Duhamel, Lucette Duhamel, Jeanne-Marie Lecomte, Jean-Charles Schwartz, Nadine Noel-Lefebvre, Claude Gros, Jean-Christophe Plaquevent
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Patent number: 5989900Abstract: A process for preparing optically active allylic alcohol derivatives comprises reacting a racemic mixture of the following formula I ##STR1## wherein R is alkyl, alkenyl, or substituted or unsubstituted aryl or arylalkyl;with acetate or anhydride under the catalysis of Pseudomonase AK, PS or K-10 lipase in the presence of an organic solvent.Type: GrantFiled: August 19, 1998Date of Patent: November 23, 1999Assignee: Development Center of BiotechnologyInventors: Adam Shih-Yuan Lee, Hsiu-Chih Yeh, Ohm-Guo Pan, Shyh-Fong Chen, Hao Ku
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Patent number: 5985274Abstract: Antibiotic 10381a.sub.1, wherein R is hydrogen, is a cytosine-containing antibiotic producible by culturing the novel microorganism Streptomyces arginensis in an aqueous medium and isolation thereof. Derivatives wherein R is a C.sub.1 to C.sub.3 alkyl ester of antibiotic 10381a.sub.1, are also disclosed along with the pharmaceutically acceptable salts of both the native and esterified forms. Antibiotic 10381a.sub.1 inhibits the growth of selected species of yeast, fungi and bacteria. This invention also relates to a novel process for the preparation of the antibiotics 10381b and to a method of using antibiotics 10381b to promote growth in meat-producing animals. These antibiotics are also obtained by the fermentation of a nutrient medium with the novel microorganism Streptomyces arginensis and are active against selected species of bacteria.Type: GrantFiled: June 5, 1995Date of Patent: November 16, 1999Assignee: Pharmacia & Upjohn CompanyInventors: Alexander D. Argoudelis, deceased, Franklin B. Shilliday, Alice L. Laborde, Scott E. Truesdell, Oldrich K. Sebek
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Patent number: 5955325Abstract: Disclosed is a method for producing a sulfated lactosamine oligosaccharide, comprising the step of allowing a sulfotransferase to act on a lactosamine oligosaccharide, the sulfotransferase transferring sulfate group to hydroxyl group at C-6 position of galactose residue in the lactosamine oligosaccharide.Type: GrantFiled: March 31, 1997Date of Patent: September 21, 1999Assignee: Seikagaku Kogyo Kabushiki KaishaInventor: Osami Habuchi