Abstract: Method and apparatus are provided for the bioconversion of toxic substrates with increased yields of product. The invention makes use of immobilized cells as biocatalyst and complexing agent in either dissolved or solid form. The invention also employs various schemes and apparatus for separating immobilized cells and complexing agent for recycle and re-use in bioconversion reactions. A preferred embodiment of the invention produces improved yields and titers of L-phenylacetyl carbinol by the bioconversion of acetaldehyde using yeast cells.
Type:
Grant
Filed:
February 28, 1991
Date of Patent:
December 22, 1992
Inventors:
Robert W. Coughlin, Wafaa M. Mahmoud, A. Halim El-Sayed
Abstract: A process for the enzymatic preparation of acetoin, particularly (+)-acetoin, employs a diacetyl reductase which can be obtained from a yeast or Lactobacillus strain.
Type:
Grant
Filed:
June 18, 1991
Date of Patent:
November 17, 1992
Assignee:
Forschungszentrum Juelich GmbH
Inventors:
Werner Hummel, Maria R. Kula, Frank Boermann
Abstract: A gram-negative, aerobic, motile, rod-shaped bacterium which is closely related to Chryseomonas luteola and Flavimonas oryzihabitans, has been found to catalyze the biodegradation and biotransformation of bisphenol alkanes, such as 2,2-bis(4-hydroxyphenyl)-propane or bisphenol A. A variety of bisphenol alkyl alcohols can be made by this procedure.
Type:
Grant
Filed:
February 10, 1992
Date of Patent:
July 21, 1992
Assignee:
General Electric Company
Inventors:
John H. Lobos, Terry K. Leib, Tah-Mun Su
Abstract: The object of the present invention is a process for obtaining irone by microbiological route.The precursors extracted from fresh iris rhizomes are subjected to the action of a fungus of the genus Botryotinia.
Abstract: The subject-matter of the present invention is a process for obtaining irone by enzymatic route.The precursors extracted from fresh iris rhizomes are subjected to the action of a peroxidizing enzymatic composition comprising oxygen and a lipoxidase or hydrogen peroxide and a peroxidase.
Type:
Grant
Filed:
February 21, 1991
Date of Patent:
March 31, 1992
Assignee:
Societe Nationale Elf Aquitaine
Inventors:
Gerard Gil, Jean Le Petit, Jean-Louis Seris
Abstract: The invention relates to a process for the accelerated ageing of iris rhizomes consisting of irradiating after harvesting, all or part of the rhizomes with ionizing radiation with a view to accelerating the transformation of triterpenoids of the rhizomes into irones. After leaving them for several days, the irones produced are extracted and are ready for use, particularly in perfumes.
Type:
Grant
Filed:
October 26, 1990
Date of Patent:
February 4, 1992
Assignees:
Commissariat a l'Energie Atomique, Universite des Sciences et Techniques du Languedoc
Inventors:
Jean-Claude Baccou, Jean-Marie Bessiere, Patrick Boisseau, Pierre Faugeras, Nicholas Jouy, Elysabette Peyrot, Yves Sauvaire
Abstract: Mutations are induced in a microorganism selected from the species Saccharomyces cerevisiae or from the species Candia 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 1-ephedrine and d-pseudoephedrine, two well-known medicinal chemicals.
Type:
Grant
Filed:
October 21, 1988
Date of Patent:
January 7, 1992
Assignee:
Synergen Associates, Inc.
Inventors:
Robert J. Seely, Donald L. Heefner, Robert V. Hageman, Michael J. Yarus, Sally A. Sullivan
Abstract: The invention relates to a process for the preparation of compounds of formulaCH.sub.3 (CHOH).sub.n --COCH.sub.2 OHin which n is an integer from 1 to 4, wherein L-serine, glyoxylic acid and an aldehyde of formula CH.sub.3 (CHOH).sub.n-1 CHO are reacted in the presence of a glyoxylate aminotransferase and a transketolase. The intermediate aldehyde CH.sub.3 (CHOH).sub.2 CHO is enzymatically prepared by the action of a polyol dehydrogenase and a xylose reductase on CH.sub.3 CHOHCOCH.sub.2 OH.
Abstract: A method for fermenting diacetyl and acetoin with a lactic acid bacterium by adding one or more additives selected from ferroporphyrin, heme protein, an animal tissue containing ferroporphyrin and blood and metal salts to a culture substrate containing a sugar source which a lactic acid bacterium can use, inoculating the lactic acid bacterium into the substrate and then aerobically culturing the bacterium with shaking or under aeration. A culture solution containing high concentrations of diacetyl and acetoin obtained by the present invention or its diacetyl concentrate is used to increase or improve the flavor of foods such as oils and fats, e.g., butter, margarine, cheeses, shortening, etc., confectionery, creams and the like.
Abstract: A gram-negative aerobic, motile, rod-shaped bacterium which is closely related to Chryseomonas luteola and Flavimonas oryzihabitans, has been found to catalyze the biodegradation and biotransformation of bisphenol alkanes, such as 2,2-bis(4-hydroxyphenyl)-propane or bisphenol A. A variety of bisphenol alkyl alcohols can be made by this procedure.
Type:
Grant
Filed:
December 11, 1990
Date of Patent:
December 3, 1991
Assignee:
General Electric Company
Inventors:
John H. Lobos, Terry K. Leib, Tah-Mun Su
Abstract: The enantiomers of formulas ##STR1## are prepared in a sequence starting from the racemic compound of formula ##STR2## wherein X is hydro or bromo when Y is bromo, or X is chloro when Y is chloro. The key step of this process involves a microbial reduction of the compound of formula (3) to give a ketone and an alcohol of high enantiomeric purity.
Abstract: There is disclosed a series of macrolides isolated from the fermentation broth of a microorganism identified as MA-5000 which morphological analysis reveals to be a strain of Streptomyces hygroscopicus. The compounds' structures are present based upon analytical studies. The compounds have antifungal activity.
Type:
Grant
Filed:
June 6, 1988
Date of Patent:
July 2, 1991
Assignee:
Merck & Co. Inc.
Inventors:
Richard W. Burg, Otto D. Hensens, Jerrold M. Liesch, Sebastian Hernandez, Lucille J. Cole
Abstract: An enzyme having .alpha.-glycerol-3-phosphate oxidase activity characterized in that it has a Km of less than 2.5 mM is disclosed, as is the production and use thereof.More particularly, such enzymes may be obtained from Propionibacterium species and may have Km values of less than 50 .mu.M, hence are advantageous for triglyceride/glycerol/.alpha.-glycerol-3-phosphate determinations and test kits.
Type:
Grant
Filed:
July 22, 1987
Date of Patent:
May 28, 1991
Assignee:
GEnzyme (U.K.) Ltd.
Inventors:
Clare H. R. Ferguson, Anne M. Macadam, Jane E. Ince, Christopher J. Knowles
Abstract: A method and compositions including a 1,2-dioxetane and a fluorescent compound is described. In particular, enzymatic triggering of a triggerable 1,2-dioxetane admixed with a surfactant and the fluorescent compound attached to a hydrocarbon to provide a co-surfactant in a micelle or other structure providing close association of these molecules is described. The method and compositions are useful in immunoassays and in DNA probes used for various purposes.
Type:
Grant
Filed:
July 27, 1988
Date of Patent:
April 2, 1991
Assignee:
The Board of Governors of Wayne State University
Abstract: A microbiological process is described for the preparation of 6-desmethyl-6-.beta.-hydroxymethyl and 6-desmethyl-6-.beta.-carboxylovastatin derivatives and 8-acyl analogs thereof.
Type:
Grant
Filed:
April 14, 1988
Date of Patent:
March 5, 1991
Assignee:
Merck & Co., Inc.
Inventors:
Joanne M. Williamson, David Houck, Edward S. Inamine
Abstract: This invention pertains to an improved process for the preparation of gamma-irone by bioconversion comprising treating an iris rhizome substrate selected from the group consisting of iris rhizomes, iris rhizome parts, iris rhizome extracts, iris rhizome extraction wastes, plant cell cultures of iris rhizomes, and mixtures thereof, with a bacteria selected from the genera group consisting of Enterobacteriacea, Pseudomonacea, the active enzyme fractions of such bacteria, and mixtures thereof, in the presence of a plant cell culture medium.
Type:
Grant
Filed:
July 24, 1989
Date of Patent:
October 16, 1990
Assignee:
Roure S.A.
Inventors:
Beatrice Belcour, Didier Courtois, Charles Ehret
Abstract: The invention deals with a process for the preparation of C.sub.5 to C.sub.10 aliphatic methyl ketones by the aerobic biotransformation of C.sub.6 to C.sub.11 fatty acids with spores of filamentous fungi of the genus Amastigomycota. The process is carried out in an inert organic solvent with a partition coefficient between water and octane superior to 4, advantageously in a C.sub.8 to C.sub.20 aliphatic hydrocarbon or a mixture of such hydrocarbons, containing at most 20% of water.The obtained methyl ketones may be used to strengthen taste or a flavoring agents.
Type:
Grant
Filed:
February 21, 1990
Date of Patent:
September 18, 1990
Assignee:
Sanofi
Inventors:
Catherine Creuly, Jean-Bernard Gros, Christian Larroche
Abstract: The process for the microbiological production of gamma (R) decanolide and/or gamma (R) octanolide involves the culture of a micro-organism selected from the group comprising Aspergillus niger, Cladosporium suaveolens, Phanerochaete chrysosporium and Pichia etchellsii in a culture medium that includes a vegetable oil, particularly castor oil, sunflower oil and coconut oil and their hydrolysates.
Type:
Grant
Filed:
August 2, 1989
Date of Patent:
August 21, 1990
Assignee:
Pernod-Ricard
Inventors:
Rosanna Cardillo, Claudio Fuganti, Giuseppe Sacerdote, Massimo Barbeni, Paolo Cabella, Francesco Squarcia
Abstract: Amines in which the amino group is on a secondary carbon atom which is chrially 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:
June 22, 1989
Date of Patent:
August 21, 1990
Assignee:
Celgene Corporation
Inventors:
David I. Stirling, Andrew L. Zeitlin, George W. Matcham
Abstract: New antibiotic A80915 and its dehydrochlorination derivatives are useful antibacterial agents. Methods of making antibiotic A80915 by culture of Streptomyces aculeolatus, NRRL 18422, and compositions containing an A80915 antibiotic also are provided.
Type:
Grant
Filed:
December 27, 1988
Date of Patent:
February 27, 1990
Assignee:
Eli Lilly and Company
Inventors:
David S. Fukuda, Jon S. Mynderse, Raymond C. Yao
Abstract: The compound 3,7-dihydroxytropolone having the formula ##STR1## is produced by fermentation of Streptomyces tropolofaciens and is found to inhibit the growth of mammalian tumors.
Type:
Grant
Filed:
January 6, 1989
Date of Patent:
November 28, 1989
Assignee:
Bristol-Myers Company
Inventors:
Hideo Kamei, Masaru Ohbayashi, Koji Tomita, Koko Sugawara, Masataka Konishi
Abstract: A method for degrading linalool using Pseudomonas strains is described. Also described are novel Pseudomons putida strains which degrade linalool and in some instances geraniol and citronellol. A method for producing 6-methyl-5-heptene-2-one using certain novel strains is also described.
Abstract: A process in which a culture of a methane-oxidizing bacterium or an extract thereof containing a methane oxidizing system is used as oxidizing agent for the oxidation of a higher short-chain alkane, an alkene or a cyclic organic compound.
Type:
Grant
Filed:
December 9, 1985
Date of Patent:
June 6, 1989
Assignee:
National Research Development Corporation
Inventors:
Howard Dalton, John Colby, David I. Stirling
Abstract: The compound 3,7-dihydroxytropolone having the formula ##STR1## is produced by fermentation of Streptomyces tropolofaciens and is found to inhibit the growth of mammalian tumors.
Type:
Grant
Filed:
November 5, 1986
Date of Patent:
May 23, 1989
Assignee:
Bristol-Myers Company
Inventors:
Hideo Kamei, Masaru Ohbayashi, Koji Tomita, Koko Sugawara, Masataka Konishi
Abstract: This invention relates to the resolution of racemic mixtures of optically active compounds, including but not limited to the stereochemical purification of chiral organic esters, amides, carboxylic acids, alcohols, and amines. Novel methods utilizing multiphase and extractive enzyme membrane bioreactors are disclosed that selectively produce pure or substantially purified optically active compounds from achiral precursors or mixtures of isomers in which one or several of those isomers are biologically inactive or otherwise lack desirable characteristics. There are immiscible solvents on either side of the membrane.
Abstract: New tetra-alkyl-2,2,5,5-cyclohexanone-4-ol-1-compounds and their sulphonyl derivatives with the general formula: ##STR1## in which: each of R and R', identical or different, represents an alkyl radical (1-5 carbons) and R" represents a hydrogen atom or a radical SO.sub.2 R"' in which R"' represents an alkyl radical (1-5 carbons) or an aryl radical (6-14 carbons), the process and the intermediates for their preparation, as well as their use in the synthesis of cyclopropane lactones of cis structure.
Type:
Grant
Filed:
June 24, 1986
Date of Patent:
June 7, 1988
Assignee:
Roussel Uclaf
Inventors:
Jean D'Angelo, Gilbert Revial, Robert Azerad, Didier Buisson
Abstract: A method of producing a non-heme haloperoxidase which is substantially resistant to inactivation, at room temperature, in up to 0.3M H.sub.2 O.sub.2 for up to 25 hours, and up to 0.5 mM HOCl for up to two minutes. One such haloperoxidase, isolated from Curvularia inaequalis, contains about 2 gram atoms of zinc per molecule. A halogenation reaction employing the enzyme can be performed at H.sub.2 O.sub.2 and hypohalous acid concentrations which produce rapid inactivation of heme-containing haloperoxidases.
Type:
Grant
Filed:
May 24, 1983
Date of Patent:
November 17, 1987
Assignee:
Cetus Corporation
Inventors:
John Geigert, Te-Ning E. Liu, Thabiso N'timkulu
Abstract: The invention relates to a process for fermenting carbohydrate- and phosphate-containing liquid media with limitation of phosphate with bacteria capable of forming butanol, acetone and/or ethanol as fermentation products performed with a total phosphate content in the medium of 1.0 to 0.4 mmoles.
Type:
Grant
Filed:
November 16, 1982
Date of Patent:
August 12, 1986
Assignee:
Gesellschaft fur Biotechnologische Forschung mbH (GBF)
Inventors:
Wolfram Andersch, Hubert Bahl, Gerhard Gottschalk
Abstract: A process in which a culture of a methane-oxidizing bacterium or an extract thereof containing a methane oxidizing system is used as oxidizing agent for the oxidation of a higher short-chain alkane, an alkene or a cyclic organic compound.
Type:
Grant
Filed:
December 28, 1982
Date of Patent:
June 10, 1986
Assignee:
National Research Development Corp.
Inventors:
Howard Dalton, John Colby, David I. Stirling
Abstract: A purified hydroxylase enzyme component A of the methane monooxygenase enzyme isolated from the soluble fraction of Methylobacterium organophilum (CRL.26) (NRRL B-11,222) is found to contain three subunits. Any component A derived from methylotrophs having the particular characteristics of this isolated component A may be employed in conjunction with the flavoprotein component C of the methane monooxygenase enzyme, preferably the flavoportein component derived from the same organism, to catalyze the oxidation of various oxidizable organic substrates to their respective oxidation products. Preferably, the substrate is propylene.
Abstract: Optically active .gamma.-decalactone is produced by culturing a microorganism capable of hydrolyzing castor oil and effecting .beta.-oxidation of the resulting hydrolysate in the presence of castor oil or castor oil hydrolysate and a co-oxidant. The resulting .gamma.-hydroxydecanoic acid is lactonized to form .gamma.-decalactone.
Abstract: A method is described for the manufacture of commercially useful alpha-halo and alpha-dihalo ketones and aldehydes from alkynes by enzymatic reaction. The alkyne is acted upon in a reaction mixture comprising a halogenating enzyme, an oxidizing agent, and a halide ion source.
Abstract: An undifferentiated symbiotic combination of alga and fungus cells, obtained directly from a lichen explant, are cultured in a media under appropriate conditions to produce aromatic lichenous substances and these substances are recovered.
Abstract: A novel asporogenic strain of Clostridium acetobutylicum is produced by growing a spore-forming strain in a continuous culturing reactor. Culturing is conducted at a dilution rate which prevents accumulation of butanol and acetone in the medium. Culturing at this dilution rate is continued until the asporogenic strain is obtained.
Type:
Grant
Filed:
November 18, 1982
Date of Patent:
June 4, 1985
Assignee:
CPC International Inc.
Inventors:
Christopher J. Lemme, Jeffrey R. Frankiewicz
Abstract: A process for the preparation of 1-carvone (spearmint flavor) comprises cultivating a carvone producing microorganism of the genus Pseudomonas in an aqueous nutrient media in the presence of 1-.alpha.- or 1-.beta.-pinene.
Abstract: Longer carbon chain polyprenyl ketone derivatives are prepared by cultivag Nocardia strain FERM-P No. 1609 in the presence of shorter carbon chain polyprenyl ketones.
Type:
Grant
Filed:
December 3, 1982
Date of Patent:
August 28, 1984
Assignees:
Eisai Co., Ltd., Director General of the Agency of Industrial Science and Technology
Abstract: An aroma distillate of a bacterial culture containing .alpha.-acetolactic acid is prepared by acidifying the bacterial culture to a pH of about 3-4 and subjecting it to water vapor distillation in the presence of oxygen for oxidation of the .alpha.-acetolactic acid to diacetyl. When 10% of the culture is driven off, a yield of 85% of diacetyl is obtained. The resultant distillate is used for aromatizing edible fats.
Type:
Grant
Filed:
August 4, 1982
Date of Patent:
June 12, 1984
Assignee:
Svenska Mejeriernas Riksforenings Ekonomi AB
Inventors:
Hans Jonsson, Hans-Erik Pettersson, Kennerth Andersson
Abstract: A process is described for the production of D-glucosone from glucose. An aqueous solution of glucose is converted substantially completely to D-glucosone by an enzymatic oxidation while removing or utilizing co-produced hydrogen peroxide. D-glucosone is a useful intermediate product which may then be converted to a desired end product.
Type:
Grant
Filed:
October 15, 1981
Date of Patent:
December 27, 1983
Assignee:
Cetus Corporation
Inventors:
William F. Amon, Jr., John Geigert, Saul L. Neidleman
Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botryodiplodia, Botryosphaeria, or Lasiodiplodia.
Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botyrodiplodia, Botryosphaeria, or Lasiodiplodia.
Abstract: A process is described which is useful as a co-process in combination with a process which employs hydrogen peroxide. The process of the invention provides a source of hydrogen peroxide along with a useful co-product, that co-product being 2-keto-D-gluconic acid or products derived therefrom. One of the first and second carbons of D-glucose is oxidized enzymatically to produce hydrogen peroxide and an intermediate product. The other of the first and second carbons of the intermediate product is then oxidized enzymatically to produce hydrogen peroxide and 2-keto-D-gluconic acid. In one form of the invention, the intermediate product is D-glucosone; the final product is 2-keto-D-gluconic acid. In the other form of the invention, the intermediate product is D-glucono-.delta.-lactone; the final product is a mixture of 2-keto-D-gluconic acid and D-isoascorbic acid.
Type:
Grant
Filed:
June 16, 1980
Date of Patent:
September 28, 1982
Assignee:
Cetus Corporation
Inventors:
Saul L. Neidleman, William F. Amon, Jr., John Geigert
Abstract: Process and equipment for advancing the oxidation state of a gaseous oxidizable organic substrate through contact with oxygen and a solid state biocatalyst. The process comprises passing through a stationary catalytic bed comprising moist, resting cells exhibiting oxygenase activity, a gaseous, oxidizable organic substrate and a gaseous source of oxygen, until the oxidative state of at least a portion of said substrate is increased, while maintaining the relative humidity in said bed at such a level that said cells remain moist and viable, and while maintaining the temperature in the vapor state. The process uses an oxygenase enzyme as a catalyst, for the incorporation of molecular oxygen directly into a specific organic molecule. The invention is of particular interest for the conversion of propylene to propylene oxide, and similar reactions that are catalyzed by mono-oxygenase enzymes.
Abstract: In the disclosed cellulase-catalyzed fermentation process for converting a cellulose- or hemicellulose-containing starting material to an organic fuel, the fermentation medium contains an efficient combination of Clostridium organisms or their enzymes. One preferred combination of organisms includes Cl. cellobioparum and Cl. acetobutylicum. Conversion of the cellulose to a liquid hydrocarbon oxidate proceeds in good yield with relativey minimal carboxylic acid production. The nondistillable residue is suitable for use as a fertilizer.
Abstract: Disclosed are methods of producing glucosone which comprises enzymatically oxidizing glucose with glucose-2-oxidase in a first zone and separating the concomitantly produced hydrogen peroxide from said first zone through a semi-permeable membrane into a second zone wherein an alkene is reacted with said hydrogen peroxide to form oxygenated products of said alkene, said membrane being permeable only to compounds of a molecular weight of less than about 100.
Abstract: Disclosed are methods of producing glucosone which comprises enzymatically oxidizing glucose with glucose-2-oxidase in a first zone and separating the concomitantly produced hydrogen peroxide from said first zone through a semi-permeable membrane into a second zone, said membrane being permeable only to compounds of a molecular weight of less than about 100.
Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botryodiplodia, Botryosphaeria, or Lasiodiplodia.
Abstract: A method for increasing the diacetyl production of a diacetyl-producing bacteria such as Streptococcus diacetylactis. Glycerol or sucrose as humectants are added to an aqueous nutrient medium such as milk having a 2% butterfat content which contains a diacetyl precursor such as sodium citrate. The bacteria are then inoculated into the humectant-containing nutrient medium. The humectant lowers the a.sub.w value of the nutrient medium so as to increase the diacetyl production of the bacteria when incubated at a temperature of from 28.degree. to 37.degree. C.
Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium comprise a compound designated MSD803 which has the lactone structure: ##STR1## as well as its free hydroxy acid form. Together with salts and esters of the free acid form, these compounds form a class of highly active hypocholesteremic and hypolipemic medicaments.
Type:
Grant
Filed:
January 23, 1980
Date of Patent:
October 13, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Richard L. Monaghan, Alfred W. Alberts, Carl H. Hoffman, George Albers-Schonberg
Abstract: Disclosed is a process for the microbiological oxidation of C.sub.1 -C.sub.6 alkanes and cycloalkanes by contacting said C.sub.1 -C.sub.6 alkanes or cycloalkanes, under aerobic conditions, in the presence of microorganisms or enzyme preparations derived therefrom, wherein said microorganisms have been aerobically grown in a nutrient containing methane. The microorganisms are newly isolated obligative and facultative methylotrophs.
Type:
Grant
Filed:
March 27, 1979
Date of Patent:
May 26, 1981
Assignee:
Exxon Research & Engineering Co.
Inventors:
Ramesh N. Patel, Ching-Tsang Hou, Allen I. Laskin