Aromatic Patents (Class 435/156)
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Patent number: 6187569Abstract: This invention relates to a biocatalytic process to produce terephthalic acid and isophthalic acid from p-xylene and m-xylene, respectively. Terephthalic acid has been prepared by oxidizing p-xylene with bacteria belonging to the genus Burkholderia. Conversion of p-xylene into terephthalic acid is accomplished by a single bacterial strain that produces all of the requisite enzymes. In addition, this invention relates to the preparation of isophthalic acid from a mixture of m- and p-xylene.Type: GrantFiled: June 29, 1999Date of Patent: February 13, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Michael G. Bramucci, Carol M. McCutchen, Vasantha Nagarajan, Stuart M. Thomas
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Patent number: 6171832Abstract: A process for preparing cis-(1S,2R)-indanediol is disclosed. The process comprises (A) fermenting a culture medium containing a yeast strain selected from the group consisting of Trichosporon cutaneum MY 1506 (ATCC 74440) and mutants thereof and 1,2-indanedione to form cis-(1S,2R)-indanediol; and (B) recovering cis-(1S,2R)-indanediol from the culture medium. A process for preparing (1S)-amino-(2R)-indanol from the recovered cis-(1S,2R)-indanediol via the Ritter reaction is also disclosed.Type: GrantFiled: April 27, 1999Date of Patent: January 9, 2001Assignee: Merck & Co., Inc.Inventors: Michael M. Chartrain, Norihiro Ikemoto, Anthony O. King
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Patent number: 6168935Abstract: An optically active alcohol substituted with one or more halogen atoms, such as optically active 4-halo-3-hydroxybutyrate esters, is efficiently synthesized by using a secondary alcohol dehydrogenase and an alcohol as a substrate accompanied by the renaturing of NADH by asymmetrical reduction of a halogen-substituted ketone such as 4-haloacetoacetate esters at low temperature. By performing the reaction at low temperature, the toxicity of a halogen-substituted ketone such as 4-haloacetoacetate esters and of the optically active alcohol such as 4-halo-3-hydroxybutyrate esters, is diminished. In this way, the accumulated concentration of an optically active alcohol substituted with one or more halogen atoms, such as 4-halo-3-hydroxybutyrate esters, may be increased while retaining the high stereoselectivity of the secondary alcohol dehydrogenase.Type: GrantFiled: February 18, 1999Date of Patent: January 2, 2001Assignee: Daicel Chemical Industries, Ltd.Inventor: Hiroaki Yamamoto
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Patent number: 6156946Abstract: The present invention is a process for transforming aromatic organic compounds and resource materials. The process includes the steps of contacting an organic material selected from the group consisting of single and/or multi-ring aromatic compounds and alkylaromatic compounds, and their heteroatom-containing analogues, crude oil, petroleum, petrochemical streams, coals, shales, coal liquids, shale oils, heavy oils and bitumens with a microorganism or enzymes in order to hydroxylate the organic material, followed by contacting the hydroxylated organic resource material so as to cause hydrogenation and/or hydrogenolysis on the material.Type: GrantFiled: October 8, 1999Date of Patent: December 5, 2000Assignee: Exxon Research and Engineering CompanyInventors: Catherine L. Coyle, Michael Siskin, David T. Ferrughelli, Michael S. P. Logan, Gerben Zylstra
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Patent number: 6133003Abstract: Using newly discovered microorganisms of the family Pseudonocardiaceae, vanillin may be produced in high yields from ferulic acid. The microorganisms are two strains of Amycolatopsis.Type: GrantFiled: August 23, 1996Date of Patent: October 17, 2000Assignee: Haarmann & Reimer GmbHInventors: Jurgen Rabenhorst, Rudolf Hopp
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Patent number: 6096859Abstract: A process of controlling the molecular weight and dispersity of poly(p-ethylphenol) and poly(m-cresol) synthesized enzymatically by varying the composition of the reaction medium. Polymers with low dispersities and molecular weights from 1000 to 3000 are synthesized in reversed micelles and biphasic systems. In comparison, reactions in bulk solvents resulted in a narrow range of molecular weights (281 to 675 with poly(p-ethylphenol) in a DMF/water system and 1,400 to 25,000 with poly(m-cresol) in an ethanol/water system). Poly(p-ethylphenol) was functionalized at hydroxyl positions with palmitoyl, cinnamoyl, and biotin groups.Type: GrantFiled: January 16, 1996Date of Patent: August 1, 2000Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Joseph A. Akkara, David L. Kaplan, Madhu Ayyagari
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Patent number: 6087540Abstract: The present invention provides a compound of the formula (I): ##STR1## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydroxy or methoxy, pharmaceutically acceptable salts or hydrates thereof, a process for producing the same, a pharmaceutical composition which comprises the same and a microorganism which belongs to Aspergillus candidus and produces the compound.Type: GrantFiled: September 3, 1998Date of Patent: July 11, 2000Assignee: Shionogi & Co., Ltd.Inventors: Toshiyuki Kamigauchi, Ryuji Suzuki
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Patent number: 6030819Abstract: The present invention pertains to a method for economical biofermentative production of 4-hydroxybenzoic acid (PHB) using genetically engineered E. coli. According to the invention, a plasmid is provided which controls the overexpression of chorismate pyruvate lyase, the bacterial enzyme which catalyzes the production of PHB from chorismate. Mutant E. coli selected with a unique two-step screening assay to overproduce chorismate have been transformed with this plasmid, providing a biocatalyst that efficiently converts glucose to PHB.Type: GrantFiled: September 28, 1998Date of Patent: February 29, 2000Assignee: General Electric CompanyInventors: Mohan Amaratunga, John Henry Lobos, Bruce Fletcher Johnson, Eric Douglas Williams
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Patent number: 6004789Abstract: A process for obtaining a pyruvate decarboxylase by isolation from a producer organism. The pyruvate decarboxylase is capable of forming (R)-(-)-phenylacetylcarbinole (I) in .gtoreq.95% enantiomer unit with a product ratio of (I) to 2-hydoxypropiophenone of .gtoreq.95%. In addition, the pyruvate decarboxylase has a specific activity with regard to phenylacetylcarbinole formation of >1U/mg. It is the aim of the invention to obtain a pyruvate decarboxylase with improved synthesis capacity concerning the formation of (R)-(-)-phenylacetylcarbinole. The process of the invention developed for this purpose is characterized in that use is made of a producing organism with a gene coding for pyruvate decarboxylase from Zymomonas mobilis, in the DNA sequence of which the tryptophane radical coding codon TGG is replaced at position 1174-1176 by a codon which codes for an amino acid radical with a reduced volume ratio.Type: GrantFiled: November 24, 1997Date of Patent: December 21, 1999Assignee: Forschungszentrum Julich GmbHInventors: Heike Bruhn, Martina Pohl, Karin Mesch, Maria-Regina Kula
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Patent number: 5994412Abstract: A compound represented by the formula I is disclosed: ##STR1## or a pharmaceutically acceptable salt or hydrate thereof. The compound has inhibitory activity against the oncoprotein Raf.Also included are pharmaceutical compositions, methods of treating cancer, cultures of the producing fungal microorganism and methods of fermentative production of the compound.Type: GrantFiled: July 2, 1998Date of Patent: November 30, 1999Assignee: Merck & Co., Inc.Inventors: Seok H. Lee, Maria T. Diez, Fernando Pelaez, Marina Mojena Sanchez, M. Dolores Vilella Amils, Hans E. Huber, Denis R. Patrick, Otto D. Hensens, Rosalind G. Jenkins, Leeyuan Huang, Annie Z. Zhao, Deborah L. Zink, Anne Dombrowski, Gerald F. Bills
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Patent number: 5986095Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.Type: GrantFiled: January 6, 1992Date of Patent: November 16, 1999Assignee: E.R. Squibb & Sons, Inc.Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5976863Abstract: Ferulic acid, vanillic acid, coniferyl alcohol and coniferyl aldehyde can be prepared from eugenol with the aid of a new Pseudomonas species.Type: GrantFiled: January 24, 1996Date of Patent: November 2, 1999Assignee: Haarmann & Reimer GmbHInventors: Rudolf Hopp, Jurgen Rabenhorst
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Patent number: 5952208Abstract: The present invention provides novel recombinant pseudomonads which contain a heterologous nucleic acid molecule comprising a nucleotide sequence encoding one or more desulfurization enzymes which are components of a biodesulfurization catalyst. The invention also provides a method of desulfurizing a carbonaceous material, such as a fossil fuel, which comprises organosulfur compounds. The method includes the steps of The method comprises the steps of (1) contacting the fossil fuel with an aqueous phase containing a recombinant biocatalyst which is capable of cleaving carbon-sulfur bonds and, optionally, a flavoprotein, thereby forming a fossil fuel and aqueous phase mixture; (2) maintaining the mixture under conditions sufficient for cleavage of the carbon-sulfur bonds of the organosulfur molecules by the biocatalyst, thereby resulting in a fossil fuel having a reduced organic sulfur content; and (3) separating the fossil fuel having a reduced organic sulfur content from the resulting aqueous phase.Type: GrantFiled: May 5, 1997Date of Patent: September 14, 1999Assignee: Energy BioSystems CorporationInventors: Aldis Darzins, Lei Xi, John D. Childs, Daniel J. Monticello, Charles H. Squires
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Patent number: 5919991Abstract: A method for isolating phenethyl alcohol in high yield is provided by fermenting L-phenylalanine within a fermentation bath to provide phenethyl alcohol. The fermented phenethyl alcohol is then contacted with an ion-exchange resin to extract the phenethyl alcohol.Type: GrantFiled: July 3, 1996Date of Patent: July 6, 1999Inventor: Ven Subbiah
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Patent number: 5914263Abstract: The invention relates to an enzymatic process for the stereoselective preparation of a hetero-bicyclic alcohol enantiomer, characterized in that a substantially pure enantiomer of the general formula ##STR1## wherein X is O, S, NH, N--(C.sub.1 -C.sub.4)alkyl or CH.sub.2 ; Y.sub.1, Y.sub.2 and Y.sub.3 are each independently hydrogen or substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro and cyano;the NO.sub.2 substituent is attached to the bicyclic ring system in the 5- or 7-position; andthe C*-atom has either the R or the S configuration;is prepared from its corresponding alcohol racemate by the following successive reaction steps:(1) stereoselective esterification,(2) separation of the alcohol from the ester produced,(3) hydrolysis of the ester to produce the corresponding alcohol enantiomer, and(4) conversion of the alcohol enantiomer into the starting racemate under basic conditions in order to allow its reuse.Type: GrantFiled: July 23, 1997Date of Patent: June 22, 1999Assignee: Duphar International Research B.V.Inventors: Nicolaas Buizer, Chris G. Kruse, Melle Van Der Laan, Georges Langrand, Gustaaf J.M. Van Scharrenburg, Maria C. Snoek
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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: 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: 5854032Abstract: Coal is treated aerobically or anaerobically to produce humic acid, volatile fatty acids, lower alcohols, and/or methane using a consortium of bacteria designated Mic-1 or KSARC56. This process can also be used to convert aromatic compounds, such as phenols and derivatives thereof, to methane and carbon dioxide.Type: GrantFiled: September 24, 1996Date of Patent: December 29, 1998Assignee: Arctech, Inc.Inventors: Kailash Chandra Srivastava, Daman S. Walia
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Patent number: 5846788Abstract: A process for the manufacture of a lignocellulose-based product from a lignocellulosic material comprises treating the lignocellulosic material and a phenolic polysaccharide having substituents containing a phenolic hydroxy group with an enzyme capable of catalyzing the oxidation of phenolic groups in the presence of an oxidizing agent.Type: GrantFiled: December 3, 1996Date of Patent: December 8, 1998Assignee: Novo Nordisk A/SInventors: Lars Saaby Pedersen, Claus Felby
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Patent number: 5840553Abstract: A novel glycerol derivative, a process for preparing the same, and a process for preparing a triazole derivative. An optically active 2-arylglycerol derivative which is novel and useful as a synthetic intermediate of medicament is provided, and furthermore, (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)-propane-1,2-diol, which is useful as an antifungal agent, is prepared.Type: GrantFiled: March 11, 1997Date of Patent: November 24, 1998Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
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Patent number: 5801023Abstract: This invention provides compounds of the following chemical formula or their pharmaceutically-acceptable salts: ##STR1## wherein R is hydrogen or chloro. Also, the present invention provides a process for the production of the compound of formula I, which comprises cultivating a microorganism having the identifying characteristics of Aspergillus fischeri var. thermomutatis ATCC 18618 or the like, and then isolating the compound of formula I from the fermentation broth. The pyrrolobenzoxazine compounds of formula I of this invention have broad antiparasitic activity, and thus are useful as antiparasitic agents, especially as anthelmintics.Type: GrantFiled: November 29, 1996Date of Patent: September 1, 1998Assignee: Pfizer Inc.Inventors: Yasuhiro Kojima, Yuji Yamauchi, Nakao Kojima, Bernard F. Bishop
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Patent number: 5773241Abstract: This invention relates to the extraction of biological compounds from plants and animals and to the preparation and tinctures and essences from the extracted materials. The materials are extracted using alcoholic and/or phosphate buffered saline solutions. The extraction step can be performed repeatedly on the residue from the previous step. The rich solution resulting from the extraction can be freeze dried for further use or employed as a fermentation feed. The fermenter product can be freeze dried for further use. The invention also makes use of the residues resulting from the extraction and fermentation reactions.Type: GrantFiled: May 12, 1997Date of Patent: June 30, 1998Inventor: Arthur Dale Ericsson
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Patent number: 5753471Abstract: A process for the biotechnological preparation of alcohols, aldehydes and carboxylic acids by oxidation of compounds of the formula R.sup.1 --C(CH.sub.3).dbd.CR.sup.2 R.sup.3, where R.sup.1, R.sup.2 and R.sup.3 have the meanings indicated in the description, with the aid of microorganisms is described.Type: GrantFiled: December 28, 1995Date of Patent: May 19, 1998Assignee: BASF AktiengesellschaftInventors: Uwe Pressler, Friedhelm Balkenhohl, Bernhard Hauer, Wolfgang Ladner, Ursula Schnell, Horst Ralf Staudenmaier
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Patent number: 5721125Abstract: The invention is a process for preparing 4-hydroxy-cinnamyl alcohols by enzymatically oxidizing 4-allyl-phenols using vanillyl alcohol oxidase. The oxidase converts eugenol and chavicol to coniferyl alcohol and coumaryl alcohol, respectively. The vanillyl alcohol oxidase may be obtained from Penicillium simplicissimum.Type: GrantFiled: June 20, 1996Date of Patent: February 24, 1998Assignee: Quest International B.V.Inventors: Wilhelmus Johannes H. van Berkel, Edserd De Jong, Marco Wilhelmus Fraaije
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Patent number: 5712146Abstract: Novel polyketides and novel methods of efficiently producing both new and known polyketides, using recombinant technology, are disclosed. In particular, a novel host-vector system is described which is used to produce polyketide synthases which in turn catalyze the production of a variety of polyketides.Type: GrantFiled: June 7, 1995Date of Patent: January 27, 1998Assignee: The Leland Stanford Junior UniversityInventors: Chaitan Khosla, David A. Hopwood, Suzanne Ebert-Khosla, Robert McDaniel, Hong Fu, Camilla Kao
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Patent number: 5688926Abstract: Etoposide phosphate is prepared by coupling dibenzyl 4'-demethyl-4-epipodophyllotoxin-4'-phosphate with 2,3-di-O-benzyl-4,6-O-ethylidene-.alpha.,.beta.-D-glucopyranose in a solvent and subsequently removing the protecting groups. The tetra-benzyl protected etoposide phosphate is recrystallized from methanol or directly crystallized from acetonitrile by adding methanol to yield substantially the pure C-1"-.beta. form. The benzyl protecting groups are simultaneously removed by hydrogenation to produce etoposide phosphate in high yields. In a further embodiment, etoposide phosphate is treated with a phosphatase enzyme to yield etoposide.Type: GrantFiled: June 7, 1995Date of Patent: November 18, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Lee J. Silverberg, Purushotham Vemishetti, John L. Dillon, Jr., John J. Usher
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Patent number: 5679557Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 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: March 13, 1996Date of Patent: October 21, 1997Assignee: Daicel Chemical Industries, LimitedInventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
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Patent number: 5677168Abstract: Process for the preparation of one or both enantiomers of 1-(4-chlorophenyl)-2-chloroethanol, which comprises an enantioselective enzymatic hydrolysis of (.+-.)-.alpha.-(4-chlorophenyl)chloroethyl acetate by means of an enzyme which is horse liver acetone powder, lipase PS from Pseudomonas fluorescens, lipase AK from Pseudomonas or the lipase from Candida antarctica, to give a mixture of unhydrolysed R-(-)-.alpha.-(4-chlorophenyl)chloroethyl acetate and S-(+)-1-(4-chlorophenyl)-2-chloroethanol, and optional separation of R-(-)-.alpha.-(4-chlorophenyl)chloroethyl acetate and optional hydrolysis of it to give R-(-)-1-(4-chlorophenyl)-2-chloroethanol and use of the enantiomers of 1-(4-chlorophenyl)-2-chlorethanol for the preparation of the enantiomers of eliprodil and of their salts.Type: GrantFiled: December 22, 1995Date of Patent: October 14, 1997Assignee: SynthelaboInventors: Lydia Zard, Arlette Tixidre
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Patent number: 5670345Abstract: Coal is treated aerobically or anaerobically to produce humic acid, volatile fatty acids, lower alcohols, and/or methane using a consortium of bacteria designated Mic-1 or KSARC56. This process can also be used to convert aromatic compounds, such as phenols and derivatives thereof, to methane and carbon dioxide.Type: GrantFiled: June 7, 1995Date of Patent: September 23, 1997Assignee: Arctech, Inc.Inventors: Kailash Chandra Srivastava, Daman S. Walia
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Patent number: 5667531Abstract: The present invention relates to isolated nucleic acid constructs containing a sequence encoding a polyporus laccase, and the laccase proteins encoded thereby.Type: GrantFiled: June 5, 1995Date of Patent: September 16, 1997Assignees: Novo Nordisk A/S, Novo Nordisk Biotech, Inc.Inventors: Debbie Sue Yaver, Feng Xu, Henrik Dalb.o slashed.ge, Palle Schneider, Dorrit A. Aaslyng
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Patent number: 5665575Abstract: The invention concerns a microbial esterase which enantioselectively cleaves (S)-1-phenylethyl acetate and is obtainable from Arthrobacter spec. (DSM 7034), Pseudomonas fluorescens (DSM 7033) or Bacillus subtilis (DSM 7035) as well as a process for enantioselectively cleaving a 1-arylalkyl ester of a carboxylic acid and a process for the production of an enantiomerically-pure 1-arylalkanol using this esterase.Type: GrantFiled: November 21, 1994Date of Patent: September 9, 1997Assignee: Boehringer Mannheim GmbHInventors: Hans-Willi Krell, Peter Rasor
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Patent number: 5665576Abstract: A method for the production of taxanes such as taxol. The method includes inducing formation of callus cells by contacting an explant tissue with a liquid medium without complete submergence of the tissue in the medium. The callus cells formed are employed in a liquid suspension cell culture to produce one or more taxanes.Type: GrantFiled: June 7, 1995Date of Patent: September 9, 1997Assignee: E. R. Squibb & Sons, Inc.Inventors: Paul M. Cino, Steven R. Schwarz, Dana L. Cazzulino
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Patent number: 5629181Abstract: A method is provided for synthesizing catechol from a biomass-derived carbon source capable of being used as a host cell having a common pathway of aromatic amino acid biosynthesis. The method comprises the steps of biocatalytically converting the carbon source to 3-dehydroshikimate in said host cell, biocatalytically converting the DHS to protocatechuate, and decarboxylating the protocatechuate to form catechol. Also provided is a heterologous E. coli transformant characterized by the expression of genes encoding transhetolase, DAHP synthase, and DHQ synthase, further characterized by the constitutive expression of structural genes encoding 3-dehydroshikimate dehydratase and protocatechuate decarboxylase.Type: GrantFiled: September 16, 1993Date of Patent: May 13, 1997Assignee: Purdue Research FoundationInventors: John W. Frost, Karen M. Draths
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Patent number: 5616496Abstract: A heterologous cell transformant is provided that biocatalytically converts a carbon source to catechol and cis, cis muconic acid. The cell transformant expresses heterologous genes encoding the enzymes 3-dehydroshikimate dehydratase, protocatechuate decarboxylase, and catechol 1,2-dioxygenase.Type: GrantFiled: June 6, 1995Date of Patent: April 1, 1997Assignee: Purdue Research FoundationInventors: John W. Frost, Karen M. Draths
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Patent number: 5605819Abstract: A process is disclosed that quantitatively bioconverts indene to (1S,2R)-indene oxide and (1S,2R)-indandiol, by the action of fungal haloperoxidase followed by various chemical step(s), e.g., adjusting the pH.Type: GrantFiled: May 19, 1995Date of Patent: February 25, 1997Assignee: Merck & Co., Inc.Inventors: Michel M. Chartrain, Neal C. Connors, George M. Garrity, Roger C. Olewinski, Jr., Thomas R. Verhoeven, Jinyou Zhang
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Patent number: 5573941Abstract: Described and claimed are the callus of Vanilla planifolia, the preparation of the same and the extraction of vanillin therefrom, and the use of ferulic acid to increase the content of vanillin.Type: GrantFiled: October 14, 1993Date of Patent: November 12, 1996Assignee: University of DelawareInventors: Gayle Davidonis, Dietrich W. Knorr, Lynn G. Romagnoli
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Patent number: 5541091Abstract: A process is described for the dimerization of a substituted aromatic compound of the formula (I): ##STR1## wherein X represents --OH, --SH or --NHR where R is H, an alkyl group or an aryl group; R.sup.1 and R.sup.2 represent an alkyl group, an aryl group, an alkenyl group, an alkynyl group, an alicyclic group, a halogen atom, an alkoxy group, an aryloxy group, a hydroxy group, or an amino group; and R.sup.3 and R.sup.4 can have the same definition as R.sup.1 and R.sup.2 and may additionally represent a hydrogen atom; which comprises reacting the substituted aromatic compound in the presence of a peroxidase enzyme, a peroxide and a radical transfer agent in an aqueous medium.Type: GrantFiled: April 5, 1995Date of Patent: July 30, 1996Assignee: Enzymol International, Inc.Inventors: Thurman M. Wheeler, Joseph Borovsky, Alexander Pokora
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Patent number: 5527702Abstract: A method for the induction of callus cells capable of producing taxanes from explant tissue by partially submerging the explant tissue in a liquid culture medium on a membrane raft, resulting in callus formation. The induction of callus cells by this method provides direct transfer of the cells formed to a liquid medium for a suspension cell culture preparation of taxanes. Thus, there is no need of a separate growth or proliferation step in the method of this invention. Furthermore, callus cells can be produced by the method; and also disclosed is a method for the use of the callus cells so produced in a suspension cell culture preparation for taxanes.Type: GrantFiled: February 23, 1994Date of Patent: June 18, 1996Assignee: E. R. Squibb & Sons, Inc.Inventors: Paul M. Cino, Steven R. Schwarz, Dana L. Cazzulino
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Patent number: 5520727Abstract: A novel water-resistant, aqueous, and versatile phenolic adhesive or glue derived from algal materials. Phenolic compounds act as an adhesive glue by binding non-specifically to both hydrophobic and hydrophilic surfaces in aqueous conditions and are useful for medical, biological, biomedical, marine, industrial and other applications. Algal derived adhesive phenolic compounds are activated with enzyme catalyst or oxidizing agents and/or cross-linked with algal carbohydrate, other fibers, or proteins.Type: GrantFiled: August 16, 1993Date of Patent: May 28, 1996Assignee: The Regents of University of CaliforniaInventors: Valerie Vreeland, Eva Grotkopp
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Patent number: 5510252Abstract: Ferulic acid, vanillic acid, coniferyl alcohol and coniferyl aldehyde can be prepared from eugenol with the aid of a new Pseudomonas species.Type: GrantFiled: June 24, 1994Date of Patent: April 23, 1996Assignee: Haarmann & Reimer GmbHInventors: Rudolf Hopp, Jurgen Rabenhorst
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Patent number: 5508180Abstract: Biocatalytic oxidative processes wherein oxidizable substrates are reacted in the presence of soybean peroxidase are described. Preferred biocatalytic oxidative reactions include the oxidation of sulfides, O-dealkylation of alkyl aryl ethers, N-dealkylation of aromatic amines, halogenation of halogen-reactive compounds and polymerization of aromatic amines. Examples of such reactions include the oxidation of alkyl aryl sulfides, the O-dealkylation of methoxybenzenes, the N-dealkylation of N,N-dimethyl aromatic amines halogenation of 5,5-dimethyl 1,3-cyclohexane dione, and the polymerization of aniline which can yield an intrinsically conductive polymer (ICP). A solution of substrate is prepared and then contacted with soybean peroxidasein the presence of a peroxide, preferably hydrogen peroxide. The reactions are preferably carried out in the presence of 10 to 100 mM calcium ions.Type: GrantFiled: September 16, 1994Date of Patent: April 16, 1996Assignee: Enzymol International, Inc.Inventors: Mark A. Johnson, Alexander R. Pokora, William L. Cyrus, Jr.
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Patent number: 5500367Abstract: The present invention relates to the gene for stilbene synthase, isolated from plants, and its use for the transformation of vectors, host organisms and plants, as well as to the production of plants which have an increased resistance to pests.Type: GrantFiled: September 24, 1993Date of Patent: March 19, 1996Assignee: Bayer AktiengesellschaftInventors: Rudiger Hain, Hans-Jorg Reif, Klaus Stenzel
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Patent number: 5500358Abstract: Catalytic antibodies are employed for catalyzing rearrangement reactions involving carbon-carbon bonds. The catalytic antibodies are generated using haptens that are transition state analogs of the such rearrangement reactions. More particularly, the haptens dispslay an electrostatic complementarity with the transition state. Since the formation of a transient positive charge in the migrating bond is a general feature of nucleophilic 1,2-shifts, it is disclosed that haptens for generating catalytic antibody directed to such reactions must incorporate such charge. Antibody catalysis of the dienone-phenol rearrangement is shown to catalyze both the hydronium ion promoted pathway and the spontaneous rearrangement pathway, indicating that the antibody stabilizes the localized positive charge of the transition state.Type: GrantFiled: August 18, 1994Date of Patent: March 19, 1996Assignee: The Scripps Research InstituteInventors: Jean-Louis Reymond, Yuanwei Chen, Richard A. Lerner
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Patent number: 5494816Abstract: DNA molecules encoding a modified tryptophan synthase beta subunit are disclosed. When expressed in a recombinant host microorganism, these polypeptide analogs enable significant levels of intracellular indole production and accumulation. In the presence of an aromatic dioxygenase enzyme, the indole so produced can be converted to indoxyl, which upon exposure to air oxidizes to indigo.Type: GrantFiled: June 21, 1994Date of Patent: February 27, 1996Assignee: Amgen Inc.Inventor: Douglas C. Murdock
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Patent number: 5470728Abstract: Cis-dihydrodiol compounds of the formula ##STR1## where n is 0 or 1 (preferably 0) are produced by the microbial oxidation of a diphenylaceylene compound of the formula ##STR2## using a mutant of a Pseudomonas bacteria at 25.degree. to 35.degree. C. and pH 6-8. The cis-dihydrodiol compound is in turn treated with an aqueous solution of a base to produce a corresponding 3-hydroxydiphenylacetylene compound or with an aqueous solution of an acid to produce a corresponding 2-hydroxyacetylene compound. The mutant strain is preferably Pseudomonas ATCC 55272.Type: GrantFiled: August 8, 1994Date of Patent: November 28, 1995Assignee: Bio-Technical ResourcesInventor: Alan D. Grund
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Patent number: 5464762Abstract: Stereospecific (S)-6-bromo-2-tetraol is a key intermediate in the chemical synthesis of the chiral drug candidate, MK499, a ventricular arrythmias suppressant. The yeast strain Trichosporon capitatum (MY 1890) was employed for the bioconversion of 6-bromo-2-tetralone to the corresponding alcohol.Type: GrantFiled: June 24, 1994Date of Patent: November 7, 1995Assignee: Merck & Co., Inc.Inventors: Michel M. Chartrain, Jayanthi Reddy, David M. Tschaen
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Patent number: 5464772Abstract: A process for producing an optically active halogen-containing alcohol having a high optical purity and represented by the following formula [I] ##STR1## wherein R.sup.1 is a halogen substituted alkyl group, R.sup.2 is a group selected from the group consisting of a substituted or unsubstituted alkyl group, alkene group, or alkyne group, and a substituted or unsubstituted phenyl group, and C having an asterisk indicates an asymmetric atom,is disclosed which process comprises subjecting a halogenated alkyl ester of a carboxylic acid represented by the following formula [II] ##STR2## wherein R.sup.1 and R.sup.2 are the same as mentioned above and R.sup.3 is a group selected from the group consisting of a substituted or unsubstituted alkyl group or alkene group, and a substituted or unsabstituted phenyl group,to asymmetric hydrolysis with an enzyme in an aqueous solution system, and the aqueous solution system may contain buffer solution and/or organic solvent.Type: GrantFiled: April 14, 1993Date of Patent: November 7, 1995Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Katutoshi Hirose, Yoshihiro Takagi, Toshihiko Otomatsu, Yoshiichi Suzuki
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Patent number: 5462865Abstract: A novel process for producing tocopherols and their precursors is described.Type: GrantFiled: March 22, 1994Date of Patent: October 31, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Achim Stocker, Wolf D. Woggon
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Patent number: 5432069Abstract: A tocopherol cyclase is produced in homogenous form which acts on phytyl benzoquinol derivatives to produce R', R', R'-tocopherols enantioselectively. The cyclase has a molecular weight of from about 48 kD to about 50 kD as determined by SDS-PAGE. The cyclase is isolated from Chlorella protothecoides, Dunaliella salina and wheat leaves of the Fidel variety.Type: GrantFiled: July 17, 1992Date of Patent: July 11, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Fiona Gruninger, Erich Hochuli, Peter K. Matzinger
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Patent number: RE35247Abstract: A process for preparing a phenolic resin which comprises preparing a reaction medium containing a phenol and a peroxidase enzyme and adding a solution of a peroxide to said medium, said peroxide being added to said medium at a rate which decreases from an initial rate of about 2 to 3 millimolar/min as the amount of phenol in said medium decreases such that the concentration of peroxide does not exceed about 12 millimolar.Type: GrantFiled: July 5, 1994Date of Patent: May 21, 1996Assignee: The Mead CorporationInventors: William L. Cyrus, Jr., Alexander R. Pokora