Propionic Or Butyric Acid Patents (Class 435/141)
  • Patent number: 5043274
    Abstract: A process for the preparation of S-2-(6-methoxy-2-naphthyl)propionic acid or a pharmaceutically acceptable salt or ester thereof, which comprises supplying R-2-(6-methoxy-2-naphthyl)-propionic acid or a pharmaceutically acceptable salt or ester thereof, to a microorganism having a stereospecific inverting enzyme system, or an extract of the microorganism containing said enzyme system, capable of converting the R enantiomer to the corresponding S enantiomer.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: August 27, 1991
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventors: Alison J. Reid, Gareth T. Phillips, Arthur F. Marx
  • Patent number: 5037759
    Abstract: The R-enantiomer of a compound of formula I: ##STR1## where Z is an optionally substituted cyclic organic moiety and C* represents an optically active carbon atom, may be prepared by supplying a substrate of formula II ##STR2## to a culture of a microorganism capable of oxidation of compound II into the R-enantiomer of I.
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: August 6, 1991
    Assignees: Shell Internationale Research Maatschappij B.V., Gist-Brocades NV
    Inventors: Kenneth H. Clifford, Gareth T. Phillips, Arthur F. Marx
  • Patent number: 5037751
    Abstract: A process for the preparation of a pharmaceutically active compound in a stereospecific form of the formula ##STR1## or a pharmaceutically acceptable salt or ester thereof, like an alkali metal salt or an alkaline earth metal salt or a pivaloyl ester, wherein R.sub.1 represents an optionally substituted aryl group such as a phenyl or naphthyl group optionally included in a heterocyclic ring system, which is optionally substituted, or represents a heteroaromatic ring system containing in addition to carbon atoms one or more atoms selected from nitrogen, sulphur and oxygen, this ring system being optionally substituted, which comprises subjecting a compound of the formula ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: August 6, 1991
    Assignee: Gist-Brocades N.V.
    Inventors: Mauro A. Bertola, Arthur F. Marx, Hein S. Koger, Wilhelmus J. Quax, Cornelis J. van der Laken, Gareth T. Phillips, Brian W. Robertson, Peter D. Watts
  • Patent number: 5034329
    Abstract: Optically active 2-arylalkanoic acids are made by enantioselective hydrolysis of the corresponding racemic amides in the presence of a microorganism, or of an enzyme derived therefrom, able selectively to hydrolyse racemic .alpha.-phenylpropionamide to S .alpha.-phenylpropionic acid.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: July 23, 1991
    Assignee: Rhone-Poulenc Sante
    Inventors: Edith Cerbelaud, Dominique Petre
  • Patent number: 4910145
    Abstract: An aqueous suspension of micro-organism cells containing a 3-hydroxybutyrate polymer are subjected to a proteolytic enzyme digestion and/or a surfactant digestion in order to solubilise cell material other than the 3-hydroxybutyrate polymer.Prior to, or during the digestion, but before any proteolytic enzyme digestion step, the suspension is heated to at least 80.degree. C. to denature nucleic acids which otherwise hinder separation of the 3-hydroxybutyrate polymer containing residue from the suspension.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: March 20, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul A. Holmes, Guan B. Lim
  • Patent number: 4886750
    Abstract: A process for the preparation of a pharmaceutically active compound in a stereospecific form of the formula ##STR1## or a pharmaceutically acceptable salt or ester thereof, like an alkali metal salt or an alkaline earth metal salt or a pivaloyl ester, wherein R.sub.1 represents an optionally substituted aryl group such as a phenyl or naphthyl group optionally included in a heterocyclic ring system, which is optionally substituted, or represents a heteroaromatic ring system containing in addition to carbon atoms one or more atoms selected from nitrogen, sulphur and oxygen, this ring system being optionally substituted, which comprises subjecting a compound of the formula ##STR2## wherein R.sub.
    Type: Grant
    Filed: January 6, 1987
    Date of Patent: December 12, 1989
    Assignees: Gist-Brocades N.V., Shell Internationale Research Mattschappij B.V.
    Inventors: Mauro A. Bertola, Arthur F. Marx, Hein S. Koger, Wilhelmus J. Quax, Cornelis J. Van der Laken, Gareth T. Phillips, Brian W. Robertson, Peter D. Watts
  • Patent number: 4865771
    Abstract: A process for preparing L(-)-carnitine chloride having the formula: ##STR1## comprising the steps of: (a) reacting a racemic ester of (R,S)-3,4-epoxybutyric acid having the formula: ##STR2## wherein R is an alkyl group having from 1-10 carbons, or a benzyl group, with an enzyme capable of selectively hydrolyzing enantiomer S(-),(b) separating said enantiomer S(-), from non-reacted ester, which is predominantly in the R(+) form;(c) reacting (1) the non-reacted ester obtained in step (b) with trimethylamine hydrochlorid or (2) the trimethylamine, to obtain thereby an ester having the formula: ##STR3## (d) hydrolyzing the ester obtain in step (c) in the presence of HCl to obtain thereby the L(-)-carnitine chloride having formula (I).The present invention is also directed to a novel class of compounds comprising R(+) enantiomers of the esters of 3,4-epoxybutyric acid.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: September 12, 1989
    Assignee: Istituto Guido Donegani S.p.A.
    Inventors: Franco Francalanci, Marco Ricci, Pietro Cesti, Carlo Venturello
  • Patent number: 4837189
    Abstract: Surfactant-modified metal catalysts which can be used in a process for hydrogenating mediators.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: June 6, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Simon, Jordanes Thanos
  • Patent number: 4814273
    Abstract: Acetic, propionic, and butyric acids are produced by a two-step fermentation process. Lactate salts formed in the second fermentation step, a biochemical acidification step, are used as the carbon source in the first fermentation step.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: March 21, 1989
    Assignee: Michigan Biotechnology Institute
    Inventors: Phillip J. Brumm, Rathin Datta
  • Patent number: 4812403
    Abstract: Process for preparing D-2-amino-2,3-dimethylbutyramide and/or L-2-amino-2,3-dimethylbutyric acid, wherein an aqueous solution of DL-2-amino-2,3-dimethylbutyramide is contacted with a preparation containing an aminoacyl amidase which has been obtained from a culture of Mycobacterium neoaurum and in that subsequently D-2-amino-2,3-dimethylbutyramide and/or L-2-amino-2,3-dimethyl-butyric acid is (are) recovered from the resulting hydrolysis mixture. The compound D-2-amino-2,3-dimethylbutyramide is novel.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: March 14, 1989
    Assignee: Stamicarbon B.V.
    Inventors: Wilhelmus H. J. Boesten, Peter J. H. Peters
  • Patent number: 4794080
    Abstract: A simultaneous sequential anaerobic fermentation process for the in vitro production of propionic and acetic acids is disclosed. The process comprises employing an obligatory two-component co-culture which maintains a relatively constant ratio of species populations over multiple passages. A first co-culture component is a Lactobacillus or Streptococcus which homofermentatively converts the hexose to lactic acid. A second microorganism in the co-culture is a Veillonella which is metabolically incapable of assimillating the hexose and converts the lactic acid product to propionic and acetic acids. The co-culture is inoculated into a nutrient growth feedstock such as whole whey or a clarified dairy whey lactose permeate which contains a metabolizable source of a hexose such as glucose, lactose or sucrose.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: December 27, 1988
    Assignee: IGENE Biotechnology, Inc.
    Inventors: Thomas D. Mays, Pamela N. Fornili
  • Patent number: 4764464
    Abstract: Proteins having a hydrophobic cavity proximate to which is a residue promoting hydrolysis of functional moieties are effective semisynthetic hydrolases. Heme proteins from which the heme has been removed usually have at least one imidazole residue proximate to the cavity, and thus act as quite effective esterases. Because the size and shape of the cavities of such proteins are capable of broad diversity a wide spectrum of substrates may be hydrolyzed by these semisynthetic enzymes.
    Type: Grant
    Filed: March 20, 1986
    Date of Patent: August 16, 1988
    Assignee: Allied-Signal Inc.
    Inventor: Haya Zemel
  • Patent number: 4758345
    Abstract: The present invention relates to an anaerobic bacterial culture of Clostridium sp. ATCC No. 53464 which solubilizes lead oxide under anaerobic conditions in coal and industrial wastes and therefore presents a method of removing lead from such wastes before they are dumped into the environment. The rate of lead dissolution during logarithmic growth of the bacteria in 40 ml medium containing 3.32 .mu.moles of lead as lead oxide was 0.042 .mu.moles ml.sup.-1 hr.sup.-1. Dissolution of lead oxide by the bacterial isolate is due to the production of metabolites and acidity in the culture medium. The major metabolites are acetic, butyric and lactic acid. Clostridium sp. ATCC No. 53464 can be used in the recovery of strategic metals from ores and wastes and also for the production of lactic acid for commercial purposes. The process yields large quantities of lactic acid as well as lead complexed in a stable form with said acids.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: July 19, 1988
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Arokiasamy J. Francis, Cleveland Dodge, Krishnachetty Chendrayan, Helen L. Quinby
  • Patent number: 4749670
    Abstract: A process for hydrogenating mediators with the aid of surfactant-modified metal catalysts, and catalysts which can be used for this purpose, are described.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: June 7, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Simon, Jordanes Thanos
  • Patent number: 4743453
    Abstract: A process for manufacture of fermented whey having a high concentration of divalent ion propionate is disclosed in which a whey medium having a solids content ranging from about 0.5% to about 18% by weight is prefermented with a galactose and glucose utilizing lactic acid producing organism, neutralized with a divalent metallic ion hydroxide and sterilized. The sterilized medium is then inoculated with a propionic acid-producing bacterium and incubated for a sufficient period of time to produce a high concentration of divalent metallic ion propionate. The divalent metallic ion is preferably calcium, and the whey medium preferably contains yeast extract.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: May 10, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: William P. Ahern, Dale F. Andrist, Lawrence E. Skogerson
  • Patent number: 4732855
    Abstract: An improved process for the production of propionic acid comprises cultivating a propionic acid-producing bacterium anaerobically in a medium which contains a simple carbohydrate, which can be converted by the bacterium to pyruvate, as well as essential minerals, vitamins, and growth factors under an overpressure of hydrogen which is effective to cause a hydrogenase produced by the bacterium to suppress the oxidation of pyruvate to acetate and carbon dioxide and to promote the formation of propionic acid.
    Type: Grant
    Filed: April 3, 1984
    Date of Patent: March 22, 1988
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Joseph G. Zeikus, Thomas E. Thompson
  • Patent number: 4710468
    Abstract: A process for preparing L-carnitine which comprises exposing .gamma.-substituted acetoacetic acid esters or amides to the fermentative enzymatic action of a microorganism which elaborates L-.beta.-hydroxyacyl CoA dehydrogenase [EC 1.1.1.35] , recovering the resulting, optically active corresponding .gamma.-substituted-.beta.-hydroxybutyric acid derivative and converting said derivative to L-carnitine. An improvement in the process is also disclosed which comprises reacting a 4-chloro-3(R)-hydroxybutyrate with sodium iodide or bromide to produce the corresponding 4-iodo- or 4-bromo-3(R)-hydroxybutyrate, converting the 4-iodo- or 4-bromo-3(R)-hydroxybutyrate to the trimethylamino-3(R)-hydroxybutyrate salt, then converting the trimethylamino-3(R)-hydroxybutyrate salt into L-carnitine. Novel chemical intermediates prepared in the processes are also disclosed.
    Type: Grant
    Filed: February 15, 1984
    Date of Patent: December 1, 1987
    Assignee: Sigma-Tau Industrie Pharmaceutiche Riunite S.p.A.
    Inventor: Charles J. Sih
  • Patent number: 4676987
    Abstract: Fermented whey having a high concentration of calcium propionate is produced by fermenting whey in a two-stage sequential fermentation process. A whey medium is fermented with a lactic acid-producing organism to produce lactic acid, neutralized with calcium hydroxide, sterilized, and then fermented with a propionic acid-producing organism. The whey medium contains yeast extract and about 0.5% to about 18.0% whey solids.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: June 30, 1987
    Assignee: Stauffer Chemical Co.
    Inventors: William P. Ahern, Dale F. Andrist, Lawrence E. Skogerson
  • Patent number: 4668628
    Abstract: Racemic mixtures of partially water-soluble esters defined by the formula ##STR1## wherein R and R.sub.1 represent hydrogen and C.sub.1 -C.sub.4 alkyl;R.sub.2 represents C.sub.1 -C.sub.4 alkyl andX represents halogen, aliphatic or aromatic groups and substituted derivatives thereof wherein R, R.sub.1 and X are differentcan be resolved by reducing the water solubility of a racemic mixture of said esters by means other than changing the chemical composition of the ester, contacting the racemic mixture of esters of reduced water solubility with a lipase enzyme from Candida cylindracea capable of stereospecifically resolving the racemic mixture of hydrolysis and stereospecifically resolving the racemic mixture.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: May 26, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Samun K. Dahod, Patricia Siuta-Mangano
  • Patent number: 4657862
    Abstract: Described is a process for the preparation of C.sub.2 -C.sub.5 alkyl esters of C.sub.4 -C.sub.5 carboxylic acids defined according to the structure: ##STR1## by means of fermentation of one or more C.sub.5 -C.sub.6 amino acids defined according to the structure: ##STR2## in the presence of a C.sub.2 -C.sub.5 alcohol according to the reaction: ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 each represent hydrogen or methyl with the proviso that at least one of R.sub.1, R.sub.2 and R.sub.3 represents methyl and wherein R represents C.sub.2 -C.sub.5 alkyl and wherein R is the same as R'. Also described are the products produced according to such process as well as their organoleptic utilities for augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, medicinal products, toothpaste, chewing tobaccos and smoking tobaccos.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: April 14, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, James A. Morris, Eugene W. Seitz
  • Patent number: 4642290
    Abstract: A process for preparing L-carnitine which comprises exposing .gamma.-substituted acetoacetic acid esters or amides to the fermentative enzymatic action of a microorganism which elaborates oxido-reductase enzymes, recovering the resulting, optically active, corresponding .gamma.-substituted-.beta.-hydroxybutyric acid derivative and converting said derivative to L-carnitine.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: February 10, 1987
    Inventor: Charles J. Sih
  • Patent number: 4628116
    Abstract: The process of extracting butyric acid and normal butanol from microbial fermentation broth, comprising contacting an aqueous solution of a microbial fermentation broth with vinyl bromide to extract any butyric acid and normal butanol which is present from the fermentation broth into the vinyl bromide. The vinyl bromide is thereafter separated from the aqueous fermentation broth and then evaporated, leaving the butyric acid and/or normal butanol in substantially pure, isolated form.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: December 9, 1986
    Inventor: Richard J. Cenedella
  • Patent number: 4601987
    Abstract: A method of resolving racemic 2-halopropionic acids by lipase-catalyzed asymmetric esterification in an organic medium is disclosed.
    Type: Grant
    Filed: February 27, 1985
    Date of Patent: July 22, 1986
    Assignee: Massachusetts Institute of Technology
    Inventors: Alexander M. Klibanov, Gerald Kirchner
  • Patent number: 4568641
    Abstract: A process for the stereospecific inversion of the [S] enantiomer of an .alpha.-aryloxypropionic acid of formula I: ##STR1## wherein G is OR.sup.1 or ##STR2## R.sup.1 is hydrogen or a protecting group and R.sup.2 is hydrogen or methyl, U and V each independently represent hydrogen or halogen, and R is a carboxyl group, or an enzymic equivalent thereof, which process comprises contacting said [S] enantiomer with a microorganism having a stereospecific inverting enzyme system, or with an extract of the microorganism contacting said enzyme system, to convert the [S] enantiomer to the corresponding [R] enantiomer.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: February 4, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventor: David W. Bewick
  • Patent number: 4565782
    Abstract: A process for the stereospecific inversion of the [S] enantiomer of an .alpha.-aryloxypropionic acid of formula I: ##STR1## wherein E is OR.sup.1 or ##STR2## R.sup.1 is an unsubstituted or substituted aryl or heterocyclic ring system, and R.sup.2 is hydrogen or methyl, U and V each independently represent hydrogen or halogen and R is a carboxyl group, or an enzymic and herbicidal equivalent thereof, which process comprises contacting said [S] enantiomer with a microorganism having a stereospecific inverting enzyme system, or with an extract of the microorganism containing said enzyme system, to convert the [S] enantiomer to the corresponding [R] enantiomer.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: January 21, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventor: David W. Bewick
  • Patent number: 4510243
    Abstract: The present invention relates to an anaerobic digestion process of wastes containing cellulose, in which, after liquefying by bringing wastes containing cellulose in slurry state into contact with facultative anaerobic bacteria with pH adjusted between 6.5-8.0 and oxidation-reduction potential controlled between -50-300 mV with oxygen supply, the liquefied slurry is then converted into methane and carbon dioxide by bringing it into contact with obligatory anaerobic bacteria to recover methane efficiently.
    Type: Grant
    Filed: October 14, 1982
    Date of Patent: April 9, 1985
    Assignee: The Agency of Industrial Science and Technology
    Inventors: Ryoichi Haga, Masahiko Ishida, Yoji Odawara
  • Patent number: 4497833
    Abstract: An improved fermented whey having mycostatic activity in which the whey is produced from the fermentation of whey using as a fermenting agent the bacterium Propionibacterium acidi-propionici #B 3568.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 5, 1985
    Assignee: Stauffer Chemical Company
    Inventor: Thomas M. Anderson
  • Patent number: 4444881
    Abstract: A process is provided for the recovery of organic acids from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium salt of the acid is isolated and heated to give the acid plus a tertiary amine.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: April 24, 1984
    Assignee: CPC International Inc.
    Inventor: Branko Urbas
  • Patent number: 4433053
    Abstract: Continuous fermentation of Alcaligenes micro-organisms capable of accumulating PHB under limitation of a nutrient required for growth, but not PHB accumulation, so that the PHB content is above 25% by weight. By means of this the carbon in the carbon and energy source, i.e. the substrate, is utilized more efficiently.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: February 21, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Lorenzo Hughes, Kenneth R. Richardson
  • Patent number: 4425432
    Abstract: A process for the propagation of microbial cells and the production of fermentation products, such as acetic and butyric acid, comprises anaerobically growing an acidogenic bacterium, such as a strain of Butyribacterium methylotrophicum ATCC 33226, in a nutrient medium containing a single carbon product, such as methanol, as the fermentation substrate or main source of assimilable carbon, accumulating the microbial cells in said medium and then separating and recovering said microbial cells and desired fermentation products from the spent media.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: January 10, 1984
    Assignee: Wisconsin Alumini Research Foundation
    Inventors: Joseph G. Zeikus, Lee H. Lynd
  • Patent number: 4377638
    Abstract: Lower aliphatic carboxylic acids of from 1 to 6 carbon atoms or salts thereof are prepared by culturing the microorganism Eubacterium limosum in a nutrient medium containing at least one member of the group consisting of carbon monoxide and a mixture of hydrogen and carbon oxide under substantially anaerobic conditions.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: March 22, 1983
    Assignee: University Patents, Inc.
    Inventors: Marvin P. Bryant, Barbara R. S. Genthner
  • Patent number: 4370418
    Abstract: Liquid (13, 13a) within a vessel (12, 12a) which receives an inflow is maintained at a predetermined level (43) by discharging liquid as necessary to compensate for the inflow. Discharge flow is drawn from below the surface (18) of the liquid to avoid clogging from scum or from other undesirable effects of surface draw off. Intake structure (34) for the discharge pump (33, 33a) has a branched flow path (47) that includes a first inlet (48) situated above the predetermined level, a second inlet (49) situated below the predetermined level and a flow junction (51) through which both inlets are communicated with the discharge pump, the junction being at the predetermined liquid level. If the liquid rises above the flow junction, the pump draws liquid through the second, subsurface inlet. If the liquid surface recedes below the flow junction, the pump aspirates air or other gas through the first inlet. Consequently liquid level is stabilized at the elevation of the flow junction.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: January 25, 1983
    Assignee: University of California
    Inventors: Benjamin L. Koopman, Antonio O. Lau, Peter F. Strom, David Jenkins
  • Patent number: 4211846
    Abstract: The invention relates to a process of manufacturing D(-)-3-hydroxybutyric acid by breeding microorganisms capable of producing said acid in a nutrient medium containing certain specific carbon source; bacterial strains especially suitable in carrying out the process; an application of the process for obtaining such microorganisms; and uses of thus produced acid.
    Type: Grant
    Filed: August 4, 1977
    Date of Patent: July 8, 1980
    Assignee: Agroferm AG
    Inventor: Robert M. Lafferty