Ketone Patents (Class 435/148)
  • Patent number: 6218158
    Abstract: This invention relates to a process for enzymic oxidation of a fatty acid to produce an oxidation product in the presence of water and oxygen wherein the fatty acid, water and enzyme for the oxidation are substantially uniformly distributed throughout a porous bed of solid support material in the substantial absence of a continuous liquid phase, oxygen is passed through the porous bed and the oxidation product is recovered from the porous bed. The invention is of particular value for production of methyl ketones from saturated fatty acids.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: April 17, 2001
    Assignee: Bush Boake Allen Limited
    Inventors: Anthony Martin Humphrey, Bridget Ann Skill, Judith L. Kinderlerer
  • Patent number: 6214573
    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: March 5, 1999
    Date of Patent: April 10, 2001
    Assignees: The Leland Stanford Junior Unv., The John Innes Institute
    Inventors: Chaitan Khosla, David A. Hopwood, Suzanne Ebert-Khosla, Robert McDaniel, Hong Fu
  • Patent number: 6210938
    Abstract: Nine efficient aldolase antibodies were generated using hapten 2. This hapten combines, in a single molecule, structural components employed for reactive immunization with structural components employed for forming a transition state analog of the aldol reaction. Characterization of two of these antibodies reveals that they are highly proficient (up to 1000-fold better than any other antibody catalyst) and enantioselective catalysts for aldol and retro-aldol reactions and exhibit enantio- and diastereo- selectivities opposite that of antibody 38C2.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: April 3, 2001
    Assignee: The Scripps Research Institute
    Inventors: Carlos F. Barbas, Richard A. Lerner, Guofu Zhong
  • Patent number: 6207409
    Abstract: Novel proteins of Flavobacterium sp. R1534 and the DNA sequences which encode these proteins are disclosed which provide an improved biosynthetic pathway from farnesyl pyrophosphate and isopentyl pyrophosphate to various carotenoid precursors and carotenoids, especially &bgr;-carotene, lycopene, zeaxanthin and cantaxanthin.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: March 27, 2001
    Assignee: Roche Vitamins Inc.
    Inventors: Hans-Peter Hohmann, Luis Pasamontes, Michel Tessier, Adolphus van Loon
  • Patent number: 6156533
    Abstract: A novel isolate of Bacillus isolated from white pine is described. The isolate is used to produce monoterpene derivatives. Also described is a pinene hydroxylase enzyme from the isolate. The enzyme is a general allylic oxidizer.
    Type: Grant
    Filed: May 14, 1998
    Date of Patent: December 5, 2000
    Assignee: Board of Trustees Operating Michigan State University
    Inventors: Patrick J. Oriel, Natarajan S. Savithiry, Weijie Fu
  • Patent number: 6150130
    Abstract: Disclosed are the following DNA strands relating to the synthesis of keto group-containing xanthophylls such as astaxanthin and the like, and the techniques relating to the production of xanthophylls by genetic engineering:A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for converting a methylene group at the 4-position of a .beta.-ionone ring into a keto group.A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for converting a methylene group at the 4-position of a 3-hydroxy-.beta.-ionone ring into a keto group.A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for adding a hydroxyl group to the 3-carbon of a 4-keto-.beta.-ionone ring.It is possible to produce a variety of xanthophylls such as canthaxanthin, astaxanthin and the like by introducing the DNA strands into an appropriate microorganism such as Escherichia coli and the like.
    Type: Grant
    Filed: June 18, 1999
    Date of Patent: November 21, 2000
    Assignees: Kirin Beer Kabushiki Kaisha, Marine Biotechnology Institute Co., Ltd.
    Inventors: Norihiko Misawa, Keiji Kondo, Susumu Kajiwara, Akihiro Yokoyama
  • Patent number: 6110520
    Abstract: A process for producing high yields of .gamma.-hexalactone and 2-pentanone from the corresponding hexanoic acid starting material is carried out with high amounts of oxygen and sugar in the presence of a mold microorganism. Fragrance compositions and foodstuff compositions are augmented and enhanced by the presence of the product compounds.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: August 29, 2000
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Fenjin He, Mohamad I. Farbood, Laura E. Kizer
  • Patent number: 6077696
    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: March 5, 1999
    Date of Patent: June 20, 2000
    Assignees: The Johns Innes Institute, The Leland Stanford Junior University
    Inventors: Chaitan Khosla, David A. Hopwood, Suzanne Ebert-Khosla, Robert McDaniel, Hong Fu, Camilla Kao
  • Patent number: 6046043
    Abstract: The present invention provides a general biocatalyst for transforming saturated carbonyl compounds to their .alpha.,.beta.-unsaturated analogs. The transformation is regio- as well as stereoselective. These catalysts are useful in the chiral resolution of carbonyl compounds as well as in the development of libraries of small molecules to screen as potential drug candidates.
    Type: Grant
    Filed: October 28, 1998
    Date of Patent: April 4, 2000
    Assignee: The Regents of the University of Michigan
    Inventors: Yerramilli V. S. N. Murthy, Vincent Massey
  • Patent number: 6046041
    Abstract: A fortified enzyme preparation of the gorgonian Pseudopterogorgia americana or Pseudopterogorgia elisabethae has been developed which efficiently transforms a variety of precursor molecules, e.g., sterols, to their corresponding metabolites, e.g., 9(11)-secosteroid in high yield. NAD, NADP, and glutamate dehydrogenase can be used as additives in this enzymatic conversion. In addition to naturally-occurring metabolites, novel secosteroids have been prepared.
    Type: Grant
    Filed: July 25, 1997
    Date of Patent: April 4, 2000
    Inventor: Russell G. Kerr
  • Patent number: 6033883
    Abstract: Hybrid and novel polyketide synthases and polyketides are produced by use of a multiple vector system. The combinatorial possibilities offered by placing the various catalytic activities of PKS systems on separate vectors permits the construction of improved libraries of PKS and polyketides. In addition, polyketides can be produced in hosts that ordinarily do not produce polyketides by supplying, along with an expression system for the desired PKS, an expression system for holo ACP synthase.
    Type: Grant
    Filed: December 11, 1997
    Date of Patent: March 7, 2000
    Assignee: KOSAN Biosciences, Inc.
    Inventors: Philip J. Barr, Daniel V. Santi, Gary W. Ashley, Rainer Ziermann
  • 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: 5985626
    Abstract: Antibodies that catalyze the aldol reaction are generated by immunization with a reactive compound that covalently traps a Lysine (Lys) residue in the binding pocket of the antibody by formation of a stable vinylogous amide, i.e., a covalent antibody/hapten complex. The resultant catalytic antibodies employ a catalytic mechanism which mimics the catalytic mechanism employed by natural class I aldolase enzymes.
    Type: Grant
    Filed: March 31, 1998
    Date of Patent: November 16, 1999
    Assignee: The Scripps Research Institute
    Inventors: Carlos F. Barbas, III, Richard A. Lerner, Juergen Wagner
  • Patent number: 5916785
    Abstract: The present invention relates to a novel alcohol/aldehyde dehydro-genase (hereinafter referred to as AADH), a process for producing the same and a process for producing aldehydes, carboxylic acids and ketones, especially 2-keto-L-gulonic acid (hereinafter referred to as 2-KGA) utilizing said enzyme.
    Type: Grant
    Filed: June 20, 1997
    Date of Patent: June 29, 1999
    Assignee: Roche Vitamins Inc.
    Inventors: Akira Asakura, Tatsuo Hoshino
  • Patent number: 5910433
    Abstract: DNA sequences are described that encode genes for synthesizing ketocarotenoids such as astaxanthin. The DNA sequences, microorganisms containing them and encoded polypeptides are described. Also described are methods to obtain related sequences and to make host cells that contain such sequences. These genes and methods are useful to impart red coloration during culture of fish and crustaceans, as coloring in food, and as antioxidants.
    Type: Grant
    Filed: April 23, 1996
    Date of Patent: June 8, 1999
    Assignee: Kirin Beer Kabushiki Kaisha
    Inventors: Susumu Kajiwara, Norihiko Misawa, Keiji Kondo
  • Patent number: 5908770
    Abstract: A process for the preparation of a saturated butanone having a terminal substituted aryl group (I) by the selective reduction of an aryl-substituted .alpha.,.beta.-unsaturated butanone (II) is presented. The aryl moiety can be mono- or polysubstituted by one or more C.sub.1 -C.sub.6 alkoxy, methylenedioxy or hydroxyl radicals and R is a C.sub.1 -C.sub.6 radical. The .alpha.,.beta.-unsaturated butanone (II) is subjected to the action of the enzymes of a yeast or of a filamentous fungus to give a mixture of (I) and an alcohol (III). (I) and (III) are isolated and purified. (III) can be enzymatically oxidized to provide (I).
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: June 1, 1999
    Assignee: Robertet S.A.
    Inventors: Daniel Joulain, Claudio Fuganti
  • Patent number: 5866380
    Abstract: Method for the production of vanillic acid and vanillin by bioconversion from ferulic acid in a medium containing phospholipids cultured with at least one microorganism from the classes Ascomycetes, Basidiomycetes or Actinomycetes. Vanillin is also produced by bioconversion of vanillic acid by at least one microorganism of the class Basidiomycetes in a medium containing cellobiose.
    Type: Grant
    Filed: June 12, 1997
    Date of Patent: February 2, 1999
    Assignee: Institut National De La Recherche Agronomique-I.N.R.A.
    Inventors: Laurence Lesage-Meessen, Michel Delattre, Mireille Haon, Marcel Asther
  • Patent number: 5858738
    Abstract: Natural products such as certain ermophilane sesquiterpenoids and derivatives thereof are described. These compounds are useful in the inhibition of HIV integrase, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. The fungal culture MF6254, Xylaria sp. (ATCC 74397) is also described and disclosed.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: January 12, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Russell B. Lingham, Jon David Polishook, Ali Shafiee, Keith C. Silverman, Sheo Bux Singh, Deborah L. Zink
  • Patent number: 5814512
    Abstract: Purpurogallin derivatives are produced useful for inhibiting catecholamine-O-methyltransferase. The derivative, 8-O-methylpurpurogallincarboxylic acid, is produced with a microorganism of the genus Absidia having all the identifying characteristics of FERM BP-4599. A pharmaceutical composition containing 8-O-methylpurpurogallincarboxylic acid or an ester or salt thereof is useful in treating Parkinson's diseases.
    Type: Grant
    Filed: February 13, 1997
    Date of Patent: September 29, 1998
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Yuki Takehana
  • Patent number: 5811273
    Abstract: Disclosed are the following DNA strands relating to the synthesis of keto group-containing xanthophylls such as astaxanthin and the like, and the techniques relating to the production of xanthophylls by genetic engineering:A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for converting a methylene group at the 4-position of .beta.-ionone ring into a keto group.A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for converting a methylene group at the 4-position of a 3-hydroxy-.beta.-ionone ring into a keto group.A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for adding a hydroxyl group to the 3-carbon of a 4-keto-.beta.-ionone ring.It is possible to produce a variety of xanthophylls such as canthaxanthin, astaxanthin and the like by introducing the DNA strands into an appropriate microorganism such as Escherichia coli and the like.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: September 22, 1998
    Assignees: Kirin Beer Kabushiki Kaisha, Marine Biotechnology Institute Co., Ltd,
    Inventors: Norihiko Misawa, Keiji Kondo, Susumu Kajiwara, Akihiro Yokoyama
  • Patent number: 5795750
    Abstract: In a process for the continuous enzyme-catalyticzed enzymatic production of hydrophobic products in an aqueous solution of a reaction mixture, the product is extracted from the product containing reaction mixture by way of a product-permeable microporous membrane into an organic solvent and the product-depleted reaction mixture is recycled.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: August 18, 1998
    Assignee: Forschungzentrum Julich GmbH
    Inventors: Wolfgang Kruse, Udo Kragl, Christian Wandrey
  • Patent number: 5770411
    Abstract: The invention relates to a microbial process for the preparation of dihydroxyacetone, the conversion of glycerol to dihydroxyacetone being carried out using a microorganism having active dehydrogenase with complete or partial recycling of biomass which is no longer capable of growth, and corresponding addition of preliminary cultures fully capable of growth.
    Type: Grant
    Filed: December 13, 1995
    Date of Patent: June 23, 1998
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Hans Leonard Ohrem, Frank Westmeier
  • Patent number: 5763234
    Abstract: A fortified enzyme preparation of the gorgonian Pseudopterogorgia americana has been developed which efficiently transforms a variety of sterols to their 9(11)-secosteroid derivative in high yield. NAD, NADP, and glutamate dehydrogenase are key additives in this enzymatic conversion. In addition to naturally-occurring metabolites, novel secosteroids have been prepared.
    Type: Grant
    Filed: July 25, 1996
    Date of Patent: June 9, 1998
    Assignee: Florida Atlantic University
    Inventor: Russell G. Kerr
  • Patent number: 5763236
    Abstract: The present invention provides a novel secondary alcohol dehydrogenase useful for the synthesis of optically active alcohol and DNA encoding said enzyme. A microorganism belonging to genus Candida was found to produce a novel secondary alcohol dehydrogenase with a high stereochemical specificity. Using said enzyme, optically active alcohols were prepared, and by cloning of DNA encoding said enzyme, the base sequence of said DNA was determined. By providing a novel secondary alcohol dehydrogenase with a high stereochemical specificity and the gene encoding said enzyme, an efficient production of optically active alcohols became possible.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: June 9, 1998
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Tomoko Kojima, Hiroaki Yamamoto, Naoki Kawada, Akinobu Matsuyama
  • Patent number: 5763237
    Abstract: Enzymatic microbial degradation of limonene with simultaneous extraction of the degradation products with a non-water miscible organic solvent is described. Microbial degradation at elevated temperatures employing both an aqueous phase containing limonene and a neat limonene phase produced .alpha.-terpineol with additional production of carvone.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: June 9, 1998
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Natarajan Savithiry, Patrick J. Oriel
  • Patent number: 5733757
    Abstract: Antibodies that catalyze the aldol reaction are generated by immunization with a reactive compound that covalently traps a Lysine (Lys) residue in the binding pocket of the antibody by formation of a stable vinylogous amide, i.e., a covalent antibody/hapten complex. The resultant catalytic antibodies employ a catalytic mechanism which mimics the catalytic mechanism employed by natural class I aldolase enzymes.
    Type: Grant
    Filed: December 15, 1995
    Date of Patent: March 31, 1998
    Assignee: The Scripps Research Institute
    Inventors: Carlos F. Barbas, III, Richard A. Lerner, Juergen Wagner
  • 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: 5707559
    Abstract: Novel light producing 1,2-dioxetanes are described of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: January 13, 1998
    Assignee: Tropix, Inc.
    Inventors: Arthur Paul Schaap, Irena Y. Bronstein
  • Patent number: 5705205
    Abstract: A process for increasing the yield of natural vanilla flavor. Green vanilla pods are hydrated. The resulting hydrated pods are ground, forming a liquid phase and a solid phase. The resulting ground hydrated product of green vanilla pods is treated with an enzymatic system including at least one enzyme. The enzyme system possesses from about 10 to about 1000 units of beta-glucose activity per gram of green vanilla pods. The ground hydrated green vanilla pods and the enzymatic system are incubated at a temperature of from about 10.degree. C. to about 40.degree. C. for a period of between about 2 hours and about 30 hours sufficient to allow the release of the vanilla flavor. The liquid phase containing the vanilla flavor is separated from the solid phase.
    Type: Grant
    Filed: September 16, 1996
    Date of Patent: January 6, 1998
    Assignee: Pernod Richard
    Inventor: Pascal Marc Brunerie
  • Patent number: 5705372
    Abstract: The present invention relates to a novel enzymatic process for the preparation of flavors, in particular of the ionones and C.sub.6 to C.sub.10 aldehydes. The invention discloses a process for the preparation of optically active alpha ionone, beta ionone, C.sub.6 aldehydes such as n-hexanal, trans-2-hexanal, C.sub.10 aldehydes such as trans-2, cis-4-decadidienal, and trans-2, trans-4-decadienal. The invention also relates to a process for the production of alcohols, particularly C.sub.6 and C.sub.10 alcohols.
    Type: Grant
    Filed: June 12, 1995
    Date of Patent: January 6, 1998
    Assignee: BFA Laboratories
    Inventors: Jean-Marc Belin, Benoit Dumont, Fran.cedilla.oise Ropert
  • Patent number: 5705369
    Abstract: The invention relates to the prehydrolysis of lignocellulose by passing an acidic or alkaline solution through solid lignocellulosic particles with removal of soluble components as they are formed. The technique permits a less severe combination of pH, temperature and time than conventional prehydrolysis. Furthermore, greater extraction of both hemicellulose and lignin occurs simultaneously in the same reactor and under the same conditions.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: January 6, 1998
    Assignee: Midwest Research Institute
    Inventors: Robert W. Torget, Kiran L. Kadam, Teh-An Hsu, George P. Philippidis, Charles E. Wyman
  • Patent number: 5702929
    Abstract: There is disclosed a novel compound having the formula ##STR1## which exhibits antifungal activity.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: December 30, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Sandra A. Morris, James E. Curotto, Gerald F. Bills, Sarah J. Dreikorn, Stanley L. Streicher, Deborah L. Zink, John R. Thompson, Angela Basilio, Fernando Pelaez, Maria Teresa Diez, Francisca Vicente
  • Patent number: 5672491
    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: May 6, 1994
    Date of Patent: September 30, 1997
    Assignees: The Leland Stanford Junior University, The John Innes Institute
    Inventors: Chaitan Khosla, David A. Hopwood, Suzanne Ebert-Khosla, Robert McDaniel, Hong Fu, Camilla Kao
  • Patent number: 5667995
    Abstract: We describe a bioorganic process for the preparation of cyclopentanone and cyclopentenone derivatives of formula ##STR1## by .beta.-oxidation of appropriate substrates, carried out by means of microorganisms.The process is useful for preparation of 3-oxo-2-pentyl-1-cyclopentaneacetic and (Z)-3-oxo-2-(2-pentenyl)-1-cyclopentane-acetic acids and their methyl esters, compounds useful in the perfume and flavor industries.
    Type: Grant
    Filed: July 31, 1996
    Date of Patent: September 16, 1997
    Assignee: Firmenich SA
    Inventor: Ian Michael Whitehead
  • Patent number: 5627057
    Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FPTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras. Furthermore, Actinoplanes sp. ATCC 55532 and Streptomces sp. ATCC 55550 are microorganisms which are capable of producing the disclosed compounds which are classified as carboxylic acid esters. In addition a method for preparing the compounds is disclosed which includes cultivating strain ATCC 55532 or strain ATCC 55550. The strains are independently capable of producing the carboxylic acid ester compounds.
    Type: Grant
    Filed: March 6, 1996
    Date of Patent: May 6, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Sheo B. Singh, George M. Garrity, Olga Genillourd, Russell B. Lingham, Isabel Martin, Mary Nallin-Omstead, Keith C. Silverman, Deborah L. Zink
  • Patent number: 5618686
    Abstract: A method of measuring the total ketone body in a sample comprising converting acetoacetic acid in the sample to 3-hydroxybutyric acid in advance and subsequently converting the whole 3-hydroxybutyric acid including 3-hydroxybutyric acid existing in the sample originally to acetoacetic acid to lead the reduction of nicotinamide adenine dinucleotide according to the action of 3-hydroxybutyrate dehydrogenase and a sample reagent thereof is disclosed. According to this invention an assay of the total ketone body in samples can be carried out conveniently, highly precisely and quickly.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: April 8, 1997
    Assignee: Nitto Boseki Co., Ltd.
    Inventors: Ryo Kojima, Yoshiro Sato, Akiko Takekawa, Katsuhiro Katayama
  • Patent number: 5578470
    Abstract: A method for preparing thiol compounds, comprising: (1) reacting cysteine by a non-enzymatical addition reaction with a compound having the formula (R.sub.1)(R.sub.2)C.dbd.C(R.sub.3)--CO--R.sub.4 via an --S-- bridge to form a cysteine conjugate, wherein the symbols R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or an optionally saturated and/or heterogeneous hydrocarbon group or wherein a combination of two groups selected from the group consisting of R.sub.1, R.sub.3 and R.sub.4, together with the carbon atoms to which the groups are bonded, form an optionally saturated and/or heterogeneous hydrocarbon ring system of five or six members; and (2) reacting the cysteine conjugate so obtained in a concentration of >1 mM conjugate with a microbial .beta.-lyase to form a thiol compound.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: November 26, 1996
    Assignee: Nederlandse Organisatie Voor Toegepast
    Inventors: Antonius Kerkenaar, Diederik J. M. Schmedding, Jan Berg
  • Patent number: 5523223
    Abstract: A keto ester reductase capable of being used in an NADH-dependent enzymatic reaction for converting .beta., .gamma. and .delta. ketonic acid esters into the corresponding optically active .beta., .gamma. and .delta. hydroxycarboxylic acid esters can be isolated from strains of Candida parapsilosis, Yarrowinia cellobiosa, Rhodococcus erythropolis or Pseudomonas acidovorans, preferably cultivated on a long -chain alkane and/or alkane acid-containing culture medium, approximately in the presence of an inductor. The microorganism is preferrably, Candida parapsilosis DSM 70125. A usable enzyme preparation can be recovered by fractionated PEG-precipitation from the cell raw extract: high specific activities (for example 1855 U/mg) may then be obtained by chromatographic purification.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: June 4, 1996
    Assignee: Forschungszentrum Julich GmbH
    Inventors: Maria-Regina Kula, Jorg Peters
  • Patent number: 5503996
    Abstract: The invention relates to the prehydrolysis of lignocellulose by passing an acidic or alkaline solution through solid lignocellulosic particles with removal of soluble components as they are formed. The technique permits a less severe combination of pH, temperature and time than conventional prehydrolysis. Furthermore, greater extraction of both hemicellulose and lignin occurs simultaneously in the same reactor and under the same conditions.
    Type: Grant
    Filed: December 27, 1994
    Date of Patent: April 2, 1996
    Assignee: Midwest Research Institute
    Inventors: Robert W. Torget, Kiran L. Kadam, Teh-An Hsu, George P. Philippidis, Charles E. Wyman
  • Patent number: 5441987
    Abstract: A compound having the formula ##STR1## which is useful as an antifungal agent and for the treatment and control of several agricultural phytopathogens, including Phytophthora infestans, is disclosed.
    Type: Grant
    Filed: August 12, 1994
    Date of Patent: August 15, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Guy H. Harris, James E. Curotto, Robert A. Giacobbe, Suzanne M. Mandala, Richard L. Monaghan, Richard K. Jansson, Joan A. Lasota
  • Patent number: 5391484
    Abstract: A process for the production of 4-pregnene-3,20-dione and its derivatives of general formula I ##STR1## in which R.sub.1 means a hydrogen atom, a fluorine atom or a methyl group,R.sub.2 represents a hydrogen atom or a hydroxy group, andR.sub.3 and R.sub.4 together symbolize a carbon-carbon bond orR.sub.3 represents a hydrogen atom, a hydroxy group or an alkanoyloxy group with up to 6 carbon atoms andR.sub.4 means a hydrogen atom or a methyl group, is described, which is characterized in that a pregnane derivative of general formula II ##STR2## in which R.sub.1, R.sub.3 and R.sub.4 have the above-mentioned meaning, symbolizes a single bond or a double bond,R.sub.5 represents a hydrogen atom, a hydroxy group or an alkanoyloxy group with at most 6 carbon atoms andR.sub.6 means a hydrogen atom or an alkanoyl group with at most 6 carbon atoms, is fermented with a bacterial culture of species Mycobacterium spec. NRRL B-3805.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: February 21, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Alfred Weber, Mario Kennecke
  • Patent number: 5387515
    Abstract: Two enzymes, one an acetylmorphine carboxyesterase (AMCE), the other a morphine dehydrogenase (MDH), have been isolated from bacteria. The AMCE degrades heroin to morphine and the MDH oxidizes morphine to morphinone, with the aid of a cofactor. More particularly, the invention pertains to a process for preparing a 6-ketone from morphine or a methyl or ethyl derivative thereof. The process comprises oxidizing morphine or an ether derivative in the presence of a morphine dehydrogenase and the cofactor NADP.sup.+. These reactions are used in detection of heroin (using the two reactions coupled together) or morphine. The enzymes can be incorporated in sensors for this purpose.
    Type: Grant
    Filed: January 19, 1994
    Date of Patent: February 7, 1995
    Assignee: British Technology Group Limited
    Inventors: Neil C. Bruce, Lauren D. G. Stephens, Christopher R. Lowe
  • Patent number: 5385833
    Abstract: The present invention provides a substantially pure culture of Pseudomonas sp. strain PED having the ATCC designation 49794. Processes for making R-configured alcohols and for transferring a hydride ion from an R-configured alcohol to the pro-R face of NAD using PED alcohol dehydrogenase isolated and purified from Pseudomonas sp. strain PED are also provided.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: January 31, 1995
    Assignee: The Scripps Research Institute
    Inventors: Curt W. Bradshaw, Chi-Huey Wong, Gwo-Jenn Shen
  • Patent number: 5342767
    Abstract: The present invention discloses the preparation of R-configured trialkylsilylethynyl .alpha.-alcohols from similarly substituted .alpha.-ketones, and vice versa, catalyzed by the alcohol dehydrogenase of Lactobacillus kefir, ATCC No. 35411. Also disclosed is the acceptance or transfer of a hydride ion from or to the pro-R face of NADPH or NADP, respectively, as catalyzed by that enzyme.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: August 30, 1994
    Assignee: The Scripps Research Institute
    Inventors: Chi-Huey Wong, Curt W. Bradshaw
  • Patent number: 5312742
    Abstract: Mutations are induced in a microorganism selected from the species Saccharomyces cerevisiae or from the species Candida flareri. The resulting mutants are cultured in the presence of a fermentation inhibitor, such as acetaldehyde, ephedrine or PAC-dione, to form colonies having resistance to the inhibitor. Cells from the colonies are isolated and tested for yield of phenyl acetyl carbinol (PAC) in a fermentation with benzaldehyde and pyruvate. Yeast cells from the colonies that produce elevated levels of PAC are selected for use in subsequent fermentations. PAC is useful as an intermediate in the preparation of l-ephedrine and d-pseudoephedrine, two well-known medicinal chemicals.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: May 17, 1994
    Assignee: Synergen Associates, Inc.
    Inventors: Robert J. Seely, Donald L. Heefner, Robert V. Hageman, Michael J. Yarus, Sally A. Sullivan
  • Patent number: 5304485
    Abstract: An organism of the Sporormiella species produces a compound having the formula ##STR1## which is useful. The compound is useful as an antifungal agent.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: April 19, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Gerald F. Bills, Fernando Pelaez
  • Patent number: 5300437
    Abstract: Amines in which the amino group is on a secondary carbon atom which is chirally substituted can be enantiomerically enriched by the action of an omega-amino acid transaminase which has the property of preferentially converting one of the two chiral forms to a ketone. The process also can be used to stereoselectively synthesize one chiral form from ketones substantially to the exclusion of the other.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: April 5, 1994
    Assignee: Celgene Corporation
    Inventors: David I. Stirling, George W. Matcham, Andrew L. Zeitlin
  • Patent number: 5284759
    Abstract: Meta-hydroxyphenylacetylenes are produced from phenyl-substituted ketal or acetal precursors. Using biotransformation processes, these precursors serve as substrates that are converted to cis-dihydrodiol intermediates. The cis-dihydrodiols can be converted chemically to the corresponding meta-substituted compounds, e.g., meta-substituted phenols, and then to m-hydroxyphenylacetylene, which is an intermediate needed to produce acetylene-terminated resins. The biotransformation step employs arene-2,3-dioxygenase in intra- or extra- cellular form.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: February 8, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Roger A. Mader, Kestutis J. Tautvydas
  • Patent number: 5236833
    Abstract: A fermented pectin-based substance containing diacetyl is prepared by fermenting an aqueous pectin slurry with a lactic acid-producing bacteria under aerobic conditions. Prior to fermentation, the pectin may be incubated with a pectinase.
    Type: Grant
    Filed: March 17, 1992
    Date of Patent: August 17, 1993
    Assignee: Nestec S.A.
    Inventors: Shirley A. Duboff, Steven S. Kwon, Dharam V. Vadehra
  • Patent number: 5182194
    Abstract: Method for preparing thiol compounds by coupling cysteine having the formula HS--CH.sub.2 --CH(NH.sub.2)COOH via and --S-- bridge to a hydrocarbon compound and subsequently reacting the cysteine conjugate obtained with .beta.-lyase to form the relevant thiol compounds.
    Type: Grant
    Filed: January 26, 1988
    Date of Patent: January 26, 1993
    Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappe Lijk Onderzoektno
    Inventors: Antonius Kerkenaar, Diederik J. M. Schmedding, Jan Berg