Aromatic Patents (Class 435/156)
  • Patent number: 6187569
    Abstract: 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: Grant
    Filed: June 29, 1999
    Date of Patent: February 13, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Michael G. Bramucci, Carol M. McCutchen, Vasantha Nagarajan, Stuart M. Thomas
  • Patent number: 6171832
    Abstract: 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: Grant
    Filed: April 27, 1999
    Date of Patent: January 9, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Michael M. Chartrain, Norihiro Ikemoto, Anthony O. King
  • Patent number: 6168935
    Abstract: 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: Grant
    Filed: February 18, 1999
    Date of Patent: January 2, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Hiroaki Yamamoto
  • Patent number: 6156946
    Abstract: 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: Grant
    Filed: October 8, 1999
    Date of Patent: December 5, 2000
    Assignee: Exxon Research and Engineering Company
    Inventors: Catherine L. Coyle, Michael Siskin, David T. Ferrughelli, Michael S. P. Logan, Gerben Zylstra
  • Patent number: 6133003
    Abstract: 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: Grant
    Filed: August 23, 1996
    Date of Patent: October 17, 2000
    Assignee: Haarmann & Reimer GmbH
    Inventors: Jurgen Rabenhorst, Rudolf Hopp
  • Patent number: 6096859
    Abstract: 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: Grant
    Filed: January 16, 1996
    Date of Patent: August 1, 2000
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Joseph A. Akkara, David L. Kaplan, Madhu Ayyagari
  • Patent number: 6087540
    Abstract: 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: Grant
    Filed: September 3, 1998
    Date of Patent: July 11, 2000
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toshiyuki Kamigauchi, Ryuji Suzuki
  • Patent number: 6030819
    Abstract: 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: Grant
    Filed: September 28, 1998
    Date of Patent: February 29, 2000
    Assignee: General Electric Company
    Inventors: Mohan Amaratunga, John Henry Lobos, Bruce Fletcher Johnson, Eric Douglas Williams
  • Patent number: 6004789
    Abstract: 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: Grant
    Filed: November 24, 1997
    Date of Patent: December 21, 1999
    Assignee: Forschungszentrum Julich GmbH
    Inventors: Heike Bruhn, Martina Pohl, Karin Mesch, Maria-Regina Kula
  • Patent number: 5994412
    Abstract: 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: Grant
    Filed: July 2, 1998
    Date of Patent: November 30, 1999
    Assignee: 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
  • Patent number: 5986095
    Abstract: 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: Grant
    Filed: January 6, 1992
    Date of Patent: November 16, 1999
    Assignee: E.R. Squibb & Sons, Inc.
    Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
  • Patent number: 5976863
    Abstract: Ferulic acid, vanillic acid, coniferyl alcohol and coniferyl aldehyde can be prepared from eugenol with the aid of a new Pseudomonas species.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: November 2, 1999
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Jurgen Rabenhorst
  • Patent number: 5952208
    Abstract: 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: Grant
    Filed: May 5, 1997
    Date of Patent: September 14, 1999
    Assignee: Energy BioSystems Corporation
    Inventors: Aldis Darzins, Lei Xi, John D. Childs, Daniel J. Monticello, Charles H. Squires
  • Patent number: 5919991
    Abstract: 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: Grant
    Filed: July 3, 1996
    Date of Patent: July 6, 1999
    Inventor: Ven Subbiah
  • Patent number: 5914263
    Abstract: 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: Grant
    Filed: July 23, 1997
    Date of Patent: June 22, 1999
    Assignee: 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
  • Patent number: 5900368
    Abstract: 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: Grant
    Filed: September 8, 1997
    Date of Patent: May 4, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Michel M. Chartrain, Hywyn R.O. Churchill, Woo-Baeg Choi, Shigeko Yamazaki
  • Patent number: 5858737
    Abstract: 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: Grant
    Filed: August 14, 1996
    Date of Patent: January 12, 1999
    Assignee: 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
  • Patent number: 5854032
    Abstract: 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: Grant
    Filed: September 24, 1996
    Date of Patent: December 29, 1998
    Assignee: Arctech, Inc.
    Inventors: Kailash Chandra Srivastava, Daman S. Walia
  • Patent number: 5846788
    Abstract: 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: Grant
    Filed: December 3, 1996
    Date of Patent: December 8, 1998
    Assignee: Novo Nordisk A/S
    Inventors: Lars Saaby Pedersen, Claus Felby
  • Patent number: 5840553
    Abstract: 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: Grant
    Filed: March 11, 1997
    Date of Patent: November 24, 1998
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
  • Patent number: 5801023
    Abstract: 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: Grant
    Filed: November 29, 1996
    Date of Patent: September 1, 1998
    Assignee: Pfizer Inc.
    Inventors: Yasuhiro Kojima, Yuji Yamauchi, Nakao Kojima, Bernard F. Bishop
  • Patent number: 5773241
    Abstract: 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: Grant
    Filed: May 12, 1997
    Date of Patent: June 30, 1998
    Inventor: Arthur Dale Ericsson
  • Patent number: 5753471
    Abstract: 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: Grant
    Filed: December 28, 1995
    Date of Patent: May 19, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Pressler, Friedhelm Balkenhohl, Bernhard Hauer, Wolfgang Ladner, Ursula Schnell, Horst Ralf Staudenmaier
  • Patent number: 5721125
    Abstract: 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: Grant
    Filed: June 20, 1996
    Date of Patent: February 24, 1998
    Assignee: Quest International B.V.
    Inventors: Wilhelmus Johannes H. van Berkel, Edserd De Jong, Marco Wilhelmus Fraaije
  • Patent number: 5712146
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: January 27, 1998
    Assignee: The Leland Stanford Junior University
    Inventors: Chaitan Khosla, David A. Hopwood, Suzanne Ebert-Khosla, Robert McDaniel, Hong Fu, Camilla Kao
  • Patent number: 5688926
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: November 18, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventors: Lee J. Silverberg, Purushotham Vemishetti, John L. Dillon, Jr., John J. Usher
  • Patent number: 5679557
    Abstract: 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: Grant
    Filed: March 13, 1996
    Date of Patent: October 21, 1997
    Assignee: Daicel Chemical Industries, Limited
    Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
  • Patent number: 5677168
    Abstract: 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: Grant
    Filed: December 22, 1995
    Date of Patent: October 14, 1997
    Assignee: Synthelabo
    Inventors: Lydia Zard, Arlette Tixidre
  • Patent number: 5670345
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: September 23, 1997
    Assignee: Arctech, Inc.
    Inventors: Kailash Chandra Srivastava, Daman S. Walia
  • Patent number: 5667531
    Abstract: The present invention relates to isolated nucleic acid constructs containing a sequence encoding a polyporus laccase, and the laccase proteins encoded thereby.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: September 16, 1997
    Assignees: Novo Nordisk A/S, Novo Nordisk Biotech, Inc.
    Inventors: Debbie Sue Yaver, Feng Xu, Henrik Dalb.o slashed.ge, Palle Schneider, Dorrit A. Aaslyng
  • Patent number: 5665575
    Abstract: 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: Grant
    Filed: November 21, 1994
    Date of Patent: September 9, 1997
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans-Willi Krell, Peter Rasor
  • Patent number: 5665576
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: September 9, 1997
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Paul M. Cino, Steven R. Schwarz, Dana L. Cazzulino
  • Patent number: 5629181
    Abstract: 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: Grant
    Filed: September 16, 1993
    Date of Patent: May 13, 1997
    Assignee: Purdue Research Foundation
    Inventors: John W. Frost, Karen M. Draths
  • Patent number: 5616496
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: April 1, 1997
    Assignee: Purdue Research Foundation
    Inventors: John W. Frost, Karen M. Draths
  • Patent number: 5605819
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: February 25, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Michel M. Chartrain, Neal C. Connors, George M. Garrity, Roger C. Olewinski, Jr., Thomas R. Verhoeven, Jinyou Zhang
  • Patent number: 5573941
    Abstract: 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: Grant
    Filed: October 14, 1993
    Date of Patent: November 12, 1996
    Assignee: University of Delaware
    Inventors: Gayle Davidonis, Dietrich W. Knorr, Lynn G. Romagnoli
  • Patent number: 5541091
    Abstract: 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: Grant
    Filed: April 5, 1995
    Date of Patent: July 30, 1996
    Assignee: Enzymol International, Inc.
    Inventors: Thurman M. Wheeler, Joseph Borovsky, Alexander Pokora
  • Patent number: 5527702
    Abstract: 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: Grant
    Filed: February 23, 1994
    Date of Patent: June 18, 1996
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Paul M. Cino, Steven R. Schwarz, Dana L. Cazzulino
  • Patent number: 5520727
    Abstract: 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: Grant
    Filed: August 16, 1993
    Date of Patent: May 28, 1996
    Assignee: The Regents of University of California
    Inventors: Valerie Vreeland, Eva Grotkopp
  • Patent number: 5510252
    Abstract: Ferulic acid, vanillic acid, coniferyl alcohol and coniferyl aldehyde can be prepared from eugenol with the aid of a new Pseudomonas species.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: April 23, 1996
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Jurgen Rabenhorst
  • Patent number: 5508180
    Abstract: 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: Grant
    Filed: September 16, 1994
    Date of Patent: April 16, 1996
    Assignee: Enzymol International, Inc.
    Inventors: Mark A. Johnson, Alexander R. Pokora, William L. Cyrus, Jr.
  • Patent number: 5500367
    Abstract: 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: Grant
    Filed: September 24, 1993
    Date of Patent: March 19, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudiger Hain, Hans-Jorg Reif, Klaus Stenzel
  • Patent number: 5500358
    Abstract: 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: Grant
    Filed: August 18, 1994
    Date of Patent: March 19, 1996
    Assignee: The Scripps Research Institute
    Inventors: Jean-Louis Reymond, Yuanwei Chen, Richard A. Lerner
  • Patent number: 5494816
    Abstract: 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: Grant
    Filed: June 21, 1994
    Date of Patent: February 27, 1996
    Assignee: Amgen Inc.
    Inventor: Douglas C. Murdock
  • Patent number: 5470728
    Abstract: 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: Grant
    Filed: August 8, 1994
    Date of Patent: November 28, 1995
    Assignee: Bio-Technical Resources
    Inventor: Alan D. Grund
  • Patent number: 5464762
    Abstract: 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: Grant
    Filed: June 24, 1994
    Date of Patent: November 7, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Michel M. Chartrain, Jayanthi Reddy, David M. Tschaen
  • Patent number: 5464772
    Abstract: 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: Grant
    Filed: April 14, 1993
    Date of Patent: November 7, 1995
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Katutoshi Hirose, Yoshihiro Takagi, Toshihiko Otomatsu, Yoshiichi Suzuki
  • Patent number: 5462865
    Abstract: A novel process for producing tocopherols and their precursors is described.
    Type: Grant
    Filed: March 22, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Achim Stocker, Wolf D. Woggon
  • Patent number: 5432069
    Abstract: 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: Grant
    Filed: July 17, 1992
    Date of Patent: July 11, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Fiona Gruninger, Erich Hochuli, Peter K. Matzinger
  • Patent number: RE35247
    Abstract: 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: Grant
    Filed: July 5, 1994
    Date of Patent: May 21, 1996
    Assignee: The Mead Corporation
    Inventors: William L. Cyrus, Jr., Alexander R. Pokora