Preparing Sulfur-containing Organic Compound Patents (Class 435/130)
  • Patent number: 5932454
    Abstract: The method comprises (1) a carboxylic acid salt providing step comprising permitting a strain of microorganism or a preparation derived from the microorganism to act upon a nitrile to thereby (a) provide at least the corresponding amide which is then hydrolyzed in the presence of a base to provide a salt of the corresponding carboxylic acid or (b) provide a salt of the corresponding carboxylic acid and (2) an electrodialysis step comprising subjecting the carboxylic acid salt provided in the step (1) to electrodialysis to provide the corresponding carboxylic acid and base. Carboxylic acids can be produced without formation of ammonium hydrogen sulfate and other byproducts. The microorganism includes microorganisms of the genera Pantoea and Gordona. The ammonia formed in the step (1) can be reused as a nitrogen source in a nitrile production line.
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: August 3, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kazuyuki Matsuoka, Akinobu Matsuyama
  • Patent number: 5919673
    Abstract: A process for the enzymatic synthase of sulfate esters is disclosed in which intermediate phosphorylated adenosine compounds are recycled to minimize enzyme inhibition. Exemplary enzymes include ATP sulfurylase, APS kinase and a sulfotransferase.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: July 6, 1999
    Assignee: The Scripps Research Institute
    Inventors: Chi-Huey Wong, Chun-Hung Lin, Gwo-Jenn Shen
  • Patent number: 5879914
    Abstract: This invention relates to recombinant DNA molecule containing a gene or genes which encode a biocatalyst capable of desulfurizing a fossil fuel which contains organic sulfur molecules. For example, the present invention encompasses a recombinant DNA molecule containing a gene or genes of a strain of Rhodococcus rhodochrous.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: March 9, 1999
    Assignee: Energy BioSystems Corporation
    Inventors: John Rambosek, Chris S. Piddington, Brian R. Kovacevich, Kevin D. Young, Sylvia A. Denome
  • Patent number: 5871954
    Abstract: Novel oxy- and thio-substituted fatty acid analog substrates of myristoylating enzymes are provided which contain an oxygen or sulfur in place of a methylene group in a carbon position from 4 to 13 in the fatty acid chain of a C.sub.13 -C.sub.14 fatty acid or alkyl ester thereof.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: February 16, 1999
    Assignee: Washington University
    Inventors: Robert O. Heuckeroth, Steven P. Adams, Jeffrey I. Gordon
  • Patent number: 5834282
    Abstract: The present invention provides a heparan sulfate 6-O-sulfotransferase for selectively introducing sulfate group into hydroxyl group at C-6 of glucosamine of heparin and heparan sulfate, having the following properties: (i) sulfate group is selectively transferred from a sulfate group donor to hydroxyl group at C-6 of N-sulfoglucosamine residue; (ii) sulfate group is transferred to CDSNS-heparan, but sulfate group is not transferred to chondroitin and chondroitin-4-sulfate; (iii) optimum reaction pH is in a range of pH 6-7; (iv) optimum ionic strength is in a range of 0.1-0.3 M (in the case of sodium chloride); and (v) the enzyme activity is inhibited by dithiothreitol and adenosine-3',5'-diphosphate, and activated by protamine.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: November 10, 1998
    Assignee: Seikagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroko Habuchi, Osami Habuchi, Koji Kimata
  • Patent number: 5817487
    Abstract: Heparan sulfate 2-O-sulfotransferase having the following properties is obtained from, for example, CHO cells:(i) action: sulfate group is transferred from a sulfate group donor selectively to the hydroxyl group at C-2 position of iduronic acid residue of a sulfate group acceptor;(ii) substrate specificity: sulfate group is transferred to heparan sulfate or CDSNS-heparin, but sulfate group is not transferred to chondroitin, chondroitin sulfate, dermatan sulfate, and keratan sulfate;(iii) optimum reaction pH: about pH 5 to 6.5;(iv) optimum ionic strength: about 50 to 200 mM when sodium chloride is used; and(v) inhibition and activation: the activity of the enzyme is increased by protamine, the activity of the enzyme is inhibited by adenosine-3',5'-diphosphate, and the activity of the enzyme is scarcely affected by dithiothreitol at 10 mM or less.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: October 6, 1998
    Assignee: Seikagaku Kogyo Kabushiki Kaisha
    Inventors: Masashi Kobayashi, Hiroko Habuchi, Osami Habuchi, Koji Kimata
  • Patent number: 5814496
    Abstract: The invention concerns a process for preparing mercapto compounds comprising the step of demethylating an S-methyl-mercapto compound of Formula I to the corresponding mercapto compound of Formula II, using a microorganism which is capable of demethylating S-methyl-3-mercapto-propionate (MMPA) to 3-mercaptopropionate (MPA) or using an enzyme preparation derivable from such microorganism. ##STR1## Preferably the group R denotes CH.sub.2 --CH.sub.2 --COOH (I is MMPA), CH.sub.2 --CH(NH.sub.2)--COOH (I is S-methyl-cystein), CH.sub.2 --CH.sub.2 --CH(NH.sub.2)--COOH (I is methionine) and CH.sub.2 --COOH (I is methylmercapto-acetate) or a salt or ester of any of these. Preferably the microorganisms are methanogenic archaea of the genus Methanosarcina or obtained by inocculating a suitable medium containing MMPA with salt marsh or marine sediment followed by one or more transfers into fresh medium containing MMPA and suppression of the growth of Bacteria, but not of Archaea in the culture e.g. with an antibiotic.
    Type: Grant
    Filed: January 8, 1997
    Date of Patent: September 29, 1998
    Assignee: Quest International B.V.
    Inventors: Theo Adriaan Hansen, Michael Jansen, Marc Jos E. C. van der Maarel
  • Patent number: 5814497
    Abstract: A method for the enzymatic hydrolysis of racemic .alpha.-substituted 4-methylthiobutyronitriles into racemic .alpha.-substituted 4-methylthiobutyric acid using a nitrilase from Alcaligenes faecalis, Gordona terrae or Rhodococcus sp.
    Type: Grant
    Filed: March 20, 1997
    Date of Patent: September 29, 1998
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Olivier Favre-Bulle, Maria-Claude Bontoux, Denis Largeau, Andre Ariagno
  • Patent number: 5795749
    Abstract: Processes using 2-deoxyribose-5-phosphate aldolase (DERA) are described for the preparation of 2-deoxyfucose and related compounds. In one embodiment, DERA is used to catalyze the condensation of acetaldehyde as donor and a 2(R)-hydroxy-3-(hydroxy or mercapto)-propionaldehyde derivative to form a 2-deoxysugar whose hydroxyls have the configuration of fucose. In another embodiment, DERA is used to catalyze the condensation of two moles of acetaldehyde as donor and one mole of a 2-substituted acetaldehyde acceptor to form a 2,4,6-trideoxyhexose via a 4-substituted-3-hydroxybutanal intermediate.
    Type: Grant
    Filed: April 5, 1995
    Date of Patent: August 18, 1998
    Assignee: The Scripps Research Institution
    Inventors: Chi-Huey Wong, Harrie J. M. Gijsen
  • Patent number: 5776765
    Abstract: A compound of formula (II), either as a single enantiomer or in an enantiomerically enriched form ##STR1## wherein: ##STR2## and ##STR3## (wherein N in the benzimidazole moiety of Het.sub.2 means that one of the carbon atoms substituted by any one of R.sub.6 to R.sub.9 optionally may be exchanged for an unsubstituted nitrogen atom; R.sub.1, R.sub.2 and R.sub.3 are the same or different and selected from hydrogen, alkyl, alkoxy optionally substituted by fluorine, alkylthio, alkoxyalkoxy, dialkylamino, piperidino, morpholino, halogen, phenylalkyl, phenylakoxy; R.sub.4 and R.sub.4, are the same or different and selected from hydrogen, alkyl, aralkyl; R.sub.5 is hydrogen, halogen, trifluoromethyl, alkyl, alkoxy; R.sub.6 -R.sub.9 are the same or different and selected from hydrogen, alkyl, alkoxy, halogen, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, oxazolyl, trifluoroalkyl or adjacent groups R.sub.6 -R.sub.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: July 7, 1998
    Assignee: Astra Aktiebolag
    Inventors: Daniel Graham, Robert Holt, Per Lindberg, Stephen Taylor
  • Patent number: 5747302
    Abstract: Flavorant compounds and compositions for food substances are prepared in a food-acceptable manner by bio-conversion of a cysteine S-complex with a food-acceptable micro-organism, particularly a yeast or filamentous fungus, which, upon incubation with the complex, splits the complex at a terminal carboxyl group in a beta position to yield a product including a thiol and at least one metabolite compound, and the product is isolated.
    Type: Grant
    Filed: October 24, 1996
    Date of Patent: May 5, 1998
    Assignee: Nestec S.A.
    Inventors: Tuong Huynh-Ba, Daniel Jaeger, Walter Matthey-Doret
  • Patent number: 5736385
    Abstract: A reaction system, wherein a cyanohydrin is converted into an optically active .alpha.-hydroxy acid or .alpha.-hydroxyamide via a treatment with a microorganism, is provided with an automatic cyanohydrin controller comprising a cyano ion detector, a regulator and a cyanohydrin supplier linked thereto. The reaction is performed while automatically controlling the cyanohydrin concentration.Thus cyanohydrin can be supplied under automatic control at a relatively low and constant concentration on the basis of its consumption ratio. The reaction rate of the catalyst can be continuously regarded as the rate-limiting factor. As a result, a decrease in the enzymatic activity during the reaction can be suppressed and an optically active .alpha.-hydroxy acid or .alpha.-hydroxyamide can be efficiently obtained at a high yield.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: April 7, 1998
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventor: Koji Tamura
  • Patent number: 5731177
    Abstract: Process for preparing S-methylmercapto and mercapto compounds comprising the step of demethylating a dimethylsulfonium compound of formula I to the corresponding S-methylmercapto compound of formula II, using a microorganism or alga which is capable of demethylating 3-dimethylsulfonium propionate (DMSP) to S-methyl-3-mercaptopropionate (MMPA), but which is incapable of further demethylating the latter compound to 3-mercaptopropionate with the same speed, or using an enzyme preparation derivable from such microorganism or alga: ##STR1## Preferably the group R denotes CH.sub.2 --CH.sub.2 --COOH (I is DMSP), CH.sub.2 --CH(NH.sub.2)--COOH (I is S-dimethyl-cystein), CH.sub.2 --Ch.sub.2 --CH (NH.sub.2) --COOH (I is S-methyl-methionine) or CH.sub.2 --COOH (I is 2-dimethylsulfonium acetate), or a salt or ester of any of these. The microorganisms are preferably marine Desulfobacterium strains, especially a Desulfobacterium autotrophicum, Desulfobacterium vacuolatum or similar strain.
    Type: Grant
    Filed: November 14, 1995
    Date of Patent: March 24, 1998
    Assignee: Quest International B.V.
    Inventors: Theo Adriaan Hansen, Marc Jos E. C. van der Maarel
  • Patent number: 5695984
    Abstract: Antibiotic 10381a.sub.1, wherein R is hydrogen, is a cytosine-containing antibiotic producible by culturing the novel microorganism Streptomyces arginensis in an aqueous medium and isolation thereof. Derivatives wherein R is a C.sub.1 to C.sub.3 alkyl ester of antibiotic 10381a.sub.1, are also disclosed along with the pharmaceutically acceptable salts of both the native and esterified forms. Antibiotic 10381a.sub.1 inhibits the growth of selected species of yeast, fungi and bacteria. This invention also relates to a novel process for the preparation of the antibiotics 10381b and to a method of using antibiotics 10381b to promote growth in meat-producing animals. These antibiotics are also obtained by the fermentation of a nutrient medium with the novel microorganism Streptomyces arginensis and are active against selected species of bacteria.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 9, 1997
    Assignee: Pharmacia & Upjohn Company
    Inventors: Alexander D. Argoudelis, deceased, Franklin B. Shilliday, Alice L. Laborde, Scott E. Truesdell, Oldrich K. Sebek
  • Patent number: 5599700
    Abstract: A process for producing carboxylic acids, in particular furoic, 3-methylthio-propionic and 2-methyl-butyric acids, as well as other short-chained, linear and branched acids consisting of the oxidation, in essentially quantitative yields, of the corresponding alcohols or aldehydes using microorganisms of the genera Saccharomyces, Hansenula, Pichia, Candida or Kluyveromyces is disclosed.
    Type: Grant
    Filed: January 13, 1994
    Date of Patent: February 4, 1997
    Assignee: Firmenich SA
    Inventors: Ian M. Whitehead, Eric Ohleyer
  • Patent number: 5597851
    Abstract: The invention is a method of using enzymes from thiophyllic microbes for selectively breaking the sulfur rubber cross-link bonds in vulcanized rubber. The process is halted at the sulfoxide or sulfone step so that a devulcanized layer is reactive with virgin rubber.
    Type: Grant
    Filed: September 14, 1995
    Date of Patent: January 28, 1997
    Assignee: Battelle Memorial Institute
    Inventors: Robert A. Romine, Lesley J. Snowden-Swan
  • 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: 5571689
    Abstract: A method for acylating peptides and proteins with the CoA-ester of diheteroatom substituted C.sub.13 to C.sub.14 myristic acid analogs catalyzed by N-myristoyltransferase is presented. In the analogs, two non-adjacent methylene groups, which are normally at positions 3-13, are replaced with oxygen or sulfur atoms.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: November 5, 1996
    Assignee: Washington University
    Inventors: Robert O. Heuckeroth, Steven P. Adams, Jeffrey I. Gordon, George W. Gokel
  • Patent number: 5565345
    Abstract: A process for preparing 5,6-dihydro-4-hydroxy-(S)-6-methyl-thieno[2,3-b]thiopyran-7,7-dioxide having the formula (II): ##STR1## which comprises subjecting 5,6-dihydro-4-oxo-(S)-6-methyl-thieno[2,3-b]thiopyran-7,7-dioxide having the formula (I): ##STR2## to the action of a microorganism to reduce the thienothiopyran derivative having the formula (I), and collecting 5,6-dihydro-4-hydroxy-(S)-6-methyl-thieno-[2,3-b]thiopyran-7,7-dioxide having the formula (II) from the reaction mixture, wherein said microorganism belongs to the genus selected from the group consisting of Ambrosiozyma, Arthroascus, Ashbya, Candida, Cryptococcus, Hansenula, Kluyveromyces, Lipomyces, Lodderomyces, Metschnikowia, Pachysolen, Pichia, Rhodosporidium, Rhodotorula, Saccharomyces, Saccharomycopsis, Schwanniomyces, Sporidiobolus, Spolobolomyces, Stephanoascus, Trigonopsis, Trichosporon and Wingea, according to which, a simple and effective. process for preparing 5,6-dihydro-4-hydroxy-(S)-6-methyl-thieno-[2,3-b]thiopyran-7,7-dioxide.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: October 15, 1996
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshihiko Yasohara, Yoshiko Tari, Noboru Ueyama, Junzo Hasegawa, Satomi Takahashi
  • Patent number: 5541092
    Abstract: A process for the preparation of a peroxycarboxylic acid of general formula (I), wherein R is an organic residue, in particular a linear or branched alkyled group, an aryl group or an alkyl aryl group each of which is optionally substituted with one or more groups, the process comprising treating a carboxylic acid of the general formula R--COOH, wherein R has the meaning indicated above, with hydrogen peroxide or a precursor thereof in the presence of an enzyme catalyst is described. The enzyme catalyst is preferably a hydrolase, such as a protease or a lipase. Also, a process for the oxidation of organic compounds with the peroxycarboxylic acids thus prepared is described.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: July 30, 1996
    Assignee: Novo Nordisk A/S
    Inventors: Ole Kirk, Frederik Bj orkling, Sven Erik Godtfredsen
  • 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: 5519130
    Abstract: Haloalkanoic acid impurities are decomposed in the presence of certain surfactants carboxymethyl cellulose or thioglycollic acids salts which may contain them as unconverted reactants by contacting them with dehalogenase enzyme.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: May 21, 1996
    Assignee: Zeneca Limited
    Inventors: David Byrom, Barbara A. Abbishaw
  • Patent number: 5516677
    Abstract: A process for organic C--S bond cleavage of a sulfur-containing organic carbonaceous material by contacting the carbonacous material with a sulfur specific reactant of membrane fragments, an enzyme, or a composition of enzymes having the ability to selectively react with sulfur by cleavage of organic C--S bonds. Preferred are sulfur specific reactants associated with cell membranes of Rhodococcus rhodochrous strain ATCC No. 53968 and Bacillus sphaericus strain ATCC No. 53969 and their derivatives which have the ability to selectively react with organic sulfur of sulfur-containing organic carbonaceous material by cleavage of organic C--S bonds.
    Type: Grant
    Filed: July 5, 1994
    Date of Patent: May 14, 1996
    Assignee: Institute of Gas Technology
    Inventor: John J. Kilbane, II
  • Patent number: 5508181
    Abstract: A process for the production of .alpha.-hydroxy acids or .alpha.-hydroxyamides in which an .alpha.-hydroxynitrile compound or a mixture consisting of an aldehyde and prussic acid, which corresponds to the nitrile compound, is allowed to undergo a microbial reaction to produce the corresponding .alpha.-hydroxy acid or .alpha.-hydroxyamide, wherein the improvement resides in that phosphite ions or hypophosphite ions are allowed to be present in the reaction system. According to the present invention, since hydrolysis or hydration of nitrile compounds can be carried out by constantly keeping a low concentration level of aldehydes which are considered to be a cause of the enzyme inhibition in the reaction system, the enzyme activity can be maintained stably for a prolonged period of time and the formed acids or amides can therefore be accumulated in a high concentration.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: April 16, 1996
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventor: Yoshihiro Hashimoto
  • 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: 5468626
    Abstract: The present invention relates to a method for separating a sulfur compound from a fossil fuel containing sulfur compounds comprising contacting said fossil fuel with a biosorption agent which binds said sulfur compound, thereby forming a sulfur-biosorption complex and separating said sulfur-biosorption complex. The method can further include introducing said separated sulfur biosorption complex to an aqueous phase having an effective amount of oxygen and water to form a reaction medium, optionally adding a biocatalyst which degrades the sulfur compound; incubating the medium for a sufficient period of time to produce an organic product, an inorganic sulfur and spent biocatalyst; and isolating said biosorption agent and/or biocatalyst from said organic product and said inorganic sulfur. The invention also relates to the preparation of the products of the oxidation reaction of organic sulfur compounds by a biocatalyst, such as 2-hydroxybiphenyl compounds.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: November 21, 1995
    Assignees: Energy BioSystems Corporation, University of Notre Dame
    Inventors: Steven W. Johnson, Daniel J. Monticello, Phillip R. Gibbs, Charles F. Kulpa
  • Patent number: 5445963
    Abstract: A process is disclosed for the separation of an enantiomerically enriched 1-tosyloxy-2-acyloxy-3-butene and an enantiomerically enriched 1-tosyloxy-2-hydroxy-3-butene from a first mixture containing both compounds. The process includes the steps of:(a) forming a solution of the mixture in an organic solvent;(b) bringing the solution formed in (a) to a temperature wherein most of the enantiomerically enriched 1-tosyloxy-2-hydroxy-3-butene precipates, leaving in solution most of the enantiomerically enriched 1-tosyloxy-2-acyloxy-3-butene; and(c) separating the precipitate formed in (b) from the solution.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: August 29, 1995
    Assignee: Eastman Chemical Company
    Inventor: Neil W. Boaz
  • Patent number: 5401709
    Abstract: The antibiotic AB-041 is described, obtained by controlled aerobic cultivation of Streptomyces sp. NCIMB 40428 in an aqueous culture medium. The antibiotic AB-041 exhibits biological activity, and in particular herbicidal activity.
    Type: Grant
    Filed: December 1, 1992
    Date of Patent: March 28, 1995
    Assignee: Ministero dell `Universita` e della Ricerca Scientifica e Tecnologica
    Inventors: Nunzio Andriollo, Alessandro Scacchi, Giorgio E. Borgonovi, Giorgio Cassani, Silvia Spera, Gianfranco Guglielmetti, Giorgio Pirali, Giovanni Confalonieri
  • Patent number: 5344778
    Abstract: A process for organic C--S bond cleavage of a sulfur-containing organic carbonaceous material by contacting the carbonacous material with a sulfur specific enzyme reactant of membrane fragments, an enzyme, or a composition of enzymes having the ability to selectively react with sulfur by cleavage of organic C--S bonds. Preferred are sulfur specific reactants associated with cell membranes of Rhodococcus rhodochrous strain ATCC No. 53968 and Bacillus sphaericus strain ATCC No. 53969 and their derivatives which have the ability to selectively react with organic sulfur of sulfur-containing organic carbonaceous material by cleavage of organic C--S bonds.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: September 6, 1994
    Assignee: Institute of Gas Technology
    Inventor: John J. Kilbane, II
  • 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: 5326702
    Abstract: A process for biologically producing an .alpha.-hydroxyamide or an .alpha.-hydroxy acid represented by formula (III) ##STR1## wherein R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group or a substituted or unsubstituted and saturated or unsaturated heterocyclic group; and X represents an amido group or a carboxyl group, comprising reacting an .alpha.-hydroxynitrile represented by formula (I): ##STR2## wherein R is as defined above, or a mixture of an aldehyde represented by formula (II):R--CHO (II)wherein R is as defined above, and hydrogen cyanide with a microorganism capable of producing such an amide or acid from the corresponding .alpha.-hydroxynitrile is disclosed, in which the reaction system contains a sulfite ion, a disulfite ion or a dithionite ion.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: July 5, 1994
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Takakazu Endo, Tomohide Yamagami, Koji Tamura
  • Patent number: 5306625
    Abstract: A microbiological process for terminal hydroxylation of ethyl groups on aromatic 5- or 6-member ring heterocycles. The hydroxylation is performed with microorganisms which:(a) contain the genes of a Pseudomonas OCT plasmid which form an active alkane monooxygenase, and(b) form no active chromosomal or plasmid-coded alcohol dehydrogenase.
    Type: Grant
    Filed: August 3, 1993
    Date of Patent: April 26, 1994
    Assignee: Lonza Ltd.
    Inventors: Andreas Kiener, Thomas Zimmermann
  • Patent number: 5306638
    Abstract: A process has been developed for the enzymatic esterification of 1,2-diol monosulfonates comprising contacting an ester; a 1,2-diol monosulfonate; an enzyme derived from a microorganism or animal organ which has stereoselective activity to asymmetrically esterify said 1,2-diol monosulfonate; in the presence of a nonhydroxylic organic solvent and an amine additive of the general formula R.sup.3.sub.2 R.sup.4 N, whereinR.sup.3 may be the same or different and is selected from hydrogen or a straight or branched C.sub.1 -C.sub.20 alkyl; andR.sup.4 is a straight or branched C.sub.1 -C.sub.20 alkyl; or an unsubstituted or substituted C.sub.3 -C.sub.20 aryl or heteroaryl group (with saisd substituent selected from C.sub.1 -C.sub.4 alkyl, halogen, or C.sub.1 -C.sub.4 alkoxy, and said hetero atom selected from nitrogen, sulfur, or oxygen);to produce a mixture of enantiomerically enriched unreacted 1,2-diol monosulfonate and the corresponding antipodal enantiomerically enriched ester.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: April 26, 1994
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5278054
    Abstract: A process for the enzymatic hydrolysis of a carboxylic acid derivative by dissolving the carboxylic acid derivative in an organic solvent which is miscible with water only to a slight extent, saturation of the organic solution with water, bringing the water-saturated organic solution into contact with a hydrolase, the hydrolysis taking place, after which the reaction solution is saturated with water again and brought into contact with the hydrolase and subsequently with water again until the desired degree of conversion is achieved.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: January 11, 1994
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Maria Buchner, Robert Estermann, Herbert Mayrhofer, Gerald Banko
  • Patent number: 5275950
    Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: January 4, 1994
    Assignee: Abbott Laboratories
    Inventors: Daniel A. Dickman, Bruce W. Horrom, Chi-Nung W. Hsiao, M. Robert Leanna, Hormoz Mazdiyasni, Howard E. Morton, Thomas M. Zydowsky, William R. Baker, Stephen L. Condon
  • Patent number: 5242816
    Abstract: A microbiological process for the terminal oxidation of alkyl groups in 5- or 6-ring heterocycles which are substituted with at least one alkyl group with more than 2 carbon atoms to carboxylic acids.
    Type: Grant
    Filed: July 3, 1991
    Date of Patent: September 7, 1993
    Assignee: Lonza Ltd.
    Inventor: Andreas Kiener
  • Patent number: 5240836
    Abstract: A method of O-methylation of a phenol, S-methylation of a thiophenal, or methylesterification of a carboxylic acid is disclosed, which involves contacting the phenol, thiophenol, or carboxylic acid with a halomethane in the presence of a fungus selected from the group consisting of Hymenochaetaceae, Polyporaceae, and Corticiaceae.
    Type: Grant
    Filed: November 23, 1990
    Date of Patent: August 31, 1993
    Assignee: The Queens University of Belfast
    Inventor: David B. Harper
  • Patent number: 5225339
    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: February 26, 1992
    Date of Patent: July 6, 1993
    Assignee: The Scripps Research Institute
    Inventors: Chi-Huey Wong, Curt W. Bradshaw
  • Patent number: 5223416
    Abstract: A process for the predominantly producing R(-)-mandelic acid or a derivative thereof which comprises subjecting (i) R,S-mandelonitrile or a derivative thereof, or (ii) a mixture of prussic acid and benzaldehyde or a derivative of benzaldehyde to the action of a microorganism selected from the group consisting of the genus Aureobacterium, Pseudomonas, Caseobacter, Alcaligenes, Acinetobacter, Brevibacterium, Nocardia, and Bacillus or treated cells thereof, which the microorganism is capable of stereospecifically hydrolyzing a nitrile group of the R,S-mandelonitrile or a derivative thereof, in a neutral or basic aqueous reaction system to produce the R(-)-mandelic acid.
    Type: Grant
    Filed: March 29, 1991
    Date of Patent: June 29, 1993
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Takakazu Endo, Koji Tamura
  • Patent number: 5223432
    Abstract: Optically pure (S)-.alpha.-[(tert-butylsulfonyl)methyl]-hydrocinnamic acid of the formula ##STR1## is prepared from racemic (RS)-.alpha.-[(tert-butylsulfonyl)-methyl]hydrocinnamic acid esters of the formula ##STR2## wherein R.sup.1 is C.sub.1-4 -alkyl, by protease-catalyzed selective hydrolysis in emulsion in an aqueous medium at a controlled pH value between about 6.5 and 8.5.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: June 29, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Beat Wirz, Wolfgang Wostl
  • Patent number: 5198341
    Abstract: A mutant Bacillus sphaericus strain ATCC No. 53969 which has the property of sulfur removal and sulfur metabolism by selective cleavage of C-S bonds in organic carbonaceous materials.
    Type: Grant
    Filed: January 14, 1991
    Date of Patent: March 30, 1993
    Assignee: Institute of Gas Technology
    Inventor: John J. Kilbane II
  • 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
  • Patent number: 5128264
    Abstract: A process for preparing optically active 1-substituted-3-hydroxybutane or its derivatives of formula (II) or (III) ##STR1## comprising treating an ester derivative of racemic 1-substituted-3-hydroxybutane of formula (I), ##STR2## wherein R.sub.1 is chloromethyl group or methyl group and R.sub.2 is p-toluenesulfonyloxy group or phenylthio group, provided that when R.sub.1 is methyl group R.sub.2 is not p-toluenesulfonyloxy group, with a lipase derived from the genus Pseudomonas.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: July 7, 1992
    Assignee: Suntory Limited
    Inventor: Charles J. Sih
  • Patent number: 5126268
    Abstract: A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched 1-arylsulfonate-2 -hydroxy-3-butene and an enantiomerically enriched 1 -arylsulfonate- 2-acyloxy-3-butene. The process includes the steps of:(a) contacting the mixture with a reagent capable of reacting with said 1-arylsulfonate-2-hydroxy-3-butene to remove the arylsulfonate group and produce a mixture of dihydroxybutene monoesters thereby forming a second mixture containing said dihydroxybutene monoesters and unreacted enantiomerically enriched 1-arylsulfonate-2-acyloxy-3-butene(b) contacting the second mixture with reagents capable of hydrolyzing all of the acyl groups in said mixture to hydroxy groups so as to produce a third mixture comprising 1,2-dihydroxy-3-butenes and enantiomerically enriched 1-arylsulfonate-2-hydroxy-3 -butene;(c) washing said third mixture with water so as to remove said 1,2-dihydroxy-3-butenes.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: June 30, 1992
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5126267
    Abstract: A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched alcohol and an enantiomerically enriched ester. The process includes the steps of:(a) contacting the mixture with a reagent capable of reacting with the hydroxy function of the alcohol, without the loss of optical purity, so as to produce a second mixture containing a base stable derivative of the enantiomerically enriched alcohol and the unreacted ester;(b) contacting the second mixture with a base capable of reacting with the ester so as to produce a third mixture containing a compound more volatile than the base stable derivative of the alcohol;(c) removing the volatile compound from the third mixture; and(d) converting the base stable derivative of the alcohol back to the enantiomerically enriched alcohol, without the loss of optical purity.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: June 30, 1992
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5106736
    Abstract: An enzymatic process for the enantiomer-specific preparation of mercapto alkanoic acids by stereoselective hydrolysis of mercapto or thioester alkanoic acid esters.
    Type: Grant
    Filed: April 23, 1991
    Date of Patent: April 21, 1992
    Assignee: E.R. Squibb & Sons, Inc.
    Inventors: Ramesh N. Patel, Laszlo J. Szarka
  • Patent number: 5070022
    Abstract: Disclosed is a process for preparing the R and S enantiomers of a compound of the formula; ##STR1## which comprises; (1) reacting an enzyme with a prochiral diester of the formula ##STR2## where M.sup.1 and M.sup.2 are the same, to produce a chiral monoester of the compound of formula II;(2) treating the chiral monoester product of step (1) with an amine and a trialkyl aluminum compound to produce the R enantiomer of the compound of formula I; or reacting the chiral monoester product of step (1) with an acid activating agent, an amine, and a base to produce the S enantiomer of the compound of formula I.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: December 3, 1991
    Assignee: Merck & Co., Inc.
    Inventors: David L. Hughes, Paul J. Reider, Joseph S. Amato, James J. Bergan, Edward J. J. Grabowski
  • Patent number: 5049496
    Abstract: A. parasiticus is employed to hydroxylate biphenyls or terphenyls. The hydroxylation reaction is enhanced by gradually adding a carbon source to the culture medium-reaction medium, preferably in an amount to maintain the ammonium level below 300 ppm. during the bioconversion phase. Employment of a mutant strain of A. parasiticus which was isolated following ultraviolet light mutagenesis to reduce its tendency to produce aflatoxins is preferred.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: September 17, 1991
    Assignee: General Electric Company
    Inventors: David P. Mobley, David K. Dietrich
  • Patent number: 5002888
    Abstract: A mutant Bacillus sphaericus strain ATC No. 53969 which has the property of sulfur removal and sulfur metabolism by selective cleavage of C-S bonds in organic carbonaceous materials.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: March 26, 1991
    Assignee: Institute of Gas Technology
    Inventor: John J. Kilbane, II
  • Patent number: 4999196
    Abstract: A novel compound, DC-107, is produced by culturing a microorganism belonging to the genus Streptomyces. It is useful as a medicine because of its antibacterial and anti-tumor activity.
    Type: Grant
    Filed: March 29, 1989
    Date of Patent: March 12, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hirofumi Nakano, Mitsunobu Hara, Isami Takahashi, Kozo Asano, Takao Iida, Makoto Morimoto