Resolution Of Optical Isomers Or Purification Of Organic Compounds Or Composition Containing Same Patents (Class 435/280)
  • Patent number: 10508070
    Abstract: The instant disclosure discloses a method for preparing 3-hydroxybutyrate salts, which includes: (1) providing ethyl 3-hydroxybutyrate or methyl 3-hydroxybutyrate, and hydrolyzing through a basic catalyst to obtain 3-hydroxybutyric acid; (2) making 3-hydroxybutyric acid reacted with an inorganic base to give 3-hydroxybutyrate. The instant disclosure adopts salt formation in water to make the reaction proceed more thoroughly, and also to save reaction time, to reduce energy consumption and material loss, to improve product yield and to lower production cost. The concentration process of the roughing (i.e. crude preparation) of 3-hydroxybutyrate is omitted.
    Type: Grant
    Filed: December 27, 2018
    Date of Patent: December 17, 2019
    Assignee: SHANGHAI SHINE HIGH INTERNATIONAL TRADE CO., LTD.
    Inventor: Yanwang Hu
  • Patent number: 9435817
    Abstract: The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the CP family. Unique antibodies derived from novel immunogens enable said methods and kits.
    Type: Grant
    Filed: August 14, 2012
    Date of Patent: September 6, 2016
    Assignee: Randox Laboratories Limited
    Inventors: Elouard Benchikh, Stephen Peter Fitzgerald, Paul John Innocenzi, Philip Andrew Lowry, Ivan Robert McConnell
  • Patent number: 9074228
    Abstract: The present invention relates to the production of optically pure secondary amines, which can be used as intermediate products in a synthesis of for instance pharmaceutical products.
    Type: Grant
    Filed: February 13, 2007
    Date of Patent: July 7, 2015
    Assignee: LONZA AG
    Inventors: Karen Robins, Uwe Bornscheuer, Matthias Höhne
  • Patent number: 9034613
    Abstract: A process for producing a compound which is (3R)-hydroxybutyl (3R)-hydroxybutyrate of formula (I) which process comprises submitting, to enantioselective reduction, a compound of the following formula (II), (III) or (IV).
    Type: Grant
    Filed: April 16, 2009
    Date of Patent: May 19, 2015
    Assignees: ISIS Innovation Limited, The United States of America, as Represented by the Secretary, Department of Health & Human Services
    Inventors: Jeremy Robertson, Kieran Clarke, Richard Lewis Veech
  • Patent number: 9005957
    Abstract: The present invention relates to a microorganism of the Corynebacterium genus that produces N-acetyl glucosamine which retains the activity of 6-phophate acetyltransferase and a method for producing N-acetyl glucosamine or glucosamine using the same.
    Type: Grant
    Filed: October 20, 2009
    Date of Patent: April 14, 2015
    Assignee: CJ Cheiljedang Corporation
    Inventors: Kuk-Ki Hong, Jin-Su Chung, Sooan Shin, Hyeran Park, Jaehyun Jo
  • Patent number: 8969068
    Abstract: A process for the purification of plasmid DNA, the process comprising treating an aqueous composition containing plasmid DNA with a polypeptide obtained from an NST1 phage to digest colanic acid and separating the plasmid DNA from the treated aqueous composition.
    Type: Grant
    Filed: April 30, 2009
    Date of Patent: March 3, 2015
    Assignee: Gradalis, Inc.
    Inventor: Nancy Smyth Templeton
  • Publication number: 20150037852
    Abstract: A method for reducing the free fatty acid content of a feedstock includes the steps of providing a free-fatty-acid-containing feedstock, treating the free-fatty-acid-containing feedstock to reduce the free fatty acid content thereof, where the step of treating includes combining at least one of an algae and a coagulant to the free-fatty-acid-containing feedstock, and producing a product from the treated feedstock.
    Type: Application
    Filed: August 4, 2014
    Publication date: February 5, 2015
    Inventors: Lu-Kwang Ju, Majid Hosseini
  • Patent number: 8945890
    Abstract: In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.
    Type: Grant
    Filed: February 25, 2013
    Date of Patent: February 3, 2015
    Assignee: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada, Reno
    Inventors: Claus Tittiger, Rubi Figueroa-Teran, Gary J. Blomquist
  • Patent number: 8932835
    Abstract: A process for the enantioselective enzymatic reduction of a keto compound of general formula I wherein R may represent any protective group for amino functions (tert. butyloxycarbonyl group (BOC), benzyloxycarbonyl group, 9-fluorenylmethoxycarbonyl group) and X?—Cl, —CN, —OH, Br, F.
    Type: Grant
    Filed: September 22, 2008
    Date of Patent: January 13, 2015
    Assignee: IEP GmbH
    Inventors: Antje Gupta, Maria Bobkova, Anke Tschentscher
  • Patent number: 8921080
    Abstract: The invention relates to an isolated polypeptide having esterase activity comprising an amino acid sequence shown in any one of SEQ ID NO's 2, 4, 6, 8, 10, 12 or 14 or a homologue thereof, comprising an amino acid substitution or deletion of one or more amino acids as shown in said SEQ ID NO's and resulting in a mutant polypeptide having an increased concentration of the fraction of the mutant polypeptide being present as an active and soluble protein in cleared lysate of the mutant polypeptide expressed in E. coli relative to the concentration of the fraction of the polypeptide without the mutation being present as an active and soluble protein in cleared lysate of the polypeptide without the one or more deletion or substitution expressed in E. coli under the same conditions. The invention also relates to nucleic acid encoding the polypeptides according to the invention, and the use of the polypeptides.
    Type: Grant
    Filed: April 26, 2010
    Date of Patent: December 30, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Martin Kietzmann, Harald Pichler, Helmut Schwab, Amin El-Heliebi, Christine Winkler, Andreas Braun
  • Publication number: 20140212957
    Abstract: A method for producing optically pure propane-1,2-diol, including the method steps: a. hydrogenation of lactides, metal-catalysed heterogenous catalysis being carried out in the presence of hydrogen, a crude product containing propane-1,2-diol being produced, and b. dynamic, kinetic racemate resolution, propane-1,2-diol of an optical purity in the range of ?99% e.e. being produced.
    Type: Application
    Filed: June 22, 2012
    Publication date: July 31, 2014
    Applicant: THYSSENKRUPP INDUSTRIAL SOLUTIONS GMBH
    Inventors: Wolfgang Tietz, Joachim Schulze, Armin Boerner, Ivan Shuklov, Klaus Kuehlein
  • Publication number: 20140186925
    Abstract: Task: There are provided a highly safe epimerase usable in food industry, and a method for producing a ketose. Resolution: The epimerase is a ketose 3-epimerase obtainable from a microorganism of the genus Arthrobacter, and having (1) substrate specificity whereby a D- or L-ketose is epimerized at position 3 to produce a corresponding D- or L-ketose, and (2) the highest substrate specificity for D-fructose and D-psicose among D- and L-ketoses.
    Type: Application
    Filed: July 5, 2012
    Publication date: July 3, 2014
    Applicants: IZUMORING CO., LTD., MATSUTANI CHEMICAL INDUSTRY CO., LTD.
    Inventors: Ken Izumori, Pushpa Kiran Gullapalli, Tomoya Shintani, Ryo Kikkawa
  • Publication number: 20140154784
    Abstract: The invention provides a method and process for the degradation of cyclic ethers that are often found in liquid streams comprising cleaning actives, through the addition of cyclic ether-degrading enzymes or enzyme-producing microbes. The cleaning actives that may be successfully treated by the methods described are selected from among anionic surfactants, nonionic surfactants, solvents, derivatives thereof, as well as mixtures of any of the foregoing.
    Type: Application
    Filed: December 3, 2012
    Publication date: June 5, 2014
    Inventor: Gregory van Buskirk
  • Patent number: 8647857
    Abstract: The present disclosure generally relates to processes employing polypeptides having colanic acid-degrading activity. The processes generally involve contacting a biological material with a polypeptide capable of digesting colanic acid. Additional process steps, such as chromatographic separation steps, are also described.
    Type: Grant
    Filed: April 30, 2009
    Date of Patent: February 11, 2014
    Assignee: Gradalis, Inc.
    Inventor: Nancy Smyth Templeton
  • Publication number: 20140011224
    Abstract: The present invention relates to a novel epoxide hydrolase enzyme which aims to achieve a high degree of resolution towards a broader range of substrates with high enantioselectivity and yields with minimal product inhibition. The invention further relates to a new bacterial strain Achromobacter sp. MTCC 5605 isolated from a petroleum-contaminated sludge sample, capable of producing the said enzyme. It is notable that the enzyme can be used as whole bacterial cell preparation, which allows continuous hydrolysis of substrates at even higher concentration and have an advantage of being recycled. The invention further relates to a process for the hydrolysis of different aryl epoxides which are potential synthons of intermediates for the synthesis of chiral amino alcohols and bioactive compounds like ?-blockers.
    Type: Application
    Filed: August 27, 2012
    Publication date: January 9, 2014
    Applicant: Council of Scientific & Industrial Research
    Inventors: Ahmed Kamal, Rohini Khanna, Chityal Ganesh Kumar, Anver Basha Shaik, Matam Shiva Kumar
  • Patent number: 8546114
    Abstract: The present invention relates to novel processes for preparing optically active Cyclopentenones of Formula (R)-1, which are useful for the preparation of Prostaglandins and analogs thereof. The invention also relates to novel Cyclopentenones prepared from the processes.
    Type: Grant
    Filed: January 18, 2006
    Date of Patent: October 1, 2013
    Assignee: Chirogate International Inc.
    Inventors: Yu-Chih Yeh, Ming-Kun Hsu, Shih-Yi Wei
  • Patent number: 8530213
    Abstract: The present disclosure relates generally to bacterial NADH oxidases and, more particularly, to novel NADH oxidases obtained from Lactobacillus plantarum, and derivatives thereof that demonstrate enzymatic activity for NADH, NADPH, or both NADH and NADPH. The compositions comprising an NADH oxidase obtained from L. plantarum or derivatives thereof include: isolated enzymes; recombinantly produced enzymes and derivatives thereof, as well as catalytically active portions thereof; nucleic acids encoding an NADH oxidase obtained from L. plantarum, derivatives thereof, and portions thereof. The methods of the present invention include isolation of NADH oxidases obtained from L. plantarum, derivatives thereof, and portions thereof, and methods for enzymatic reactions comprising NADH oxidase obtained from L. plantarum, including the production of enantiomer-enriched organic compounds.
    Type: Grant
    Filed: December 2, 2010
    Date of Patent: September 10, 2013
    Assignees: Georgia Tech Research Corporation, Emory University
    Inventors: Andreas Bommarius, Bettina Bommarius, Jun-Ichiro Hirano, Vaijayanthi Thangavel, Jonathan Taejoo Park
  • Publication number: 20130230878
    Abstract: In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.
    Type: Application
    Filed: February 25, 2013
    Publication date: September 5, 2013
    Applicant: Board of Regents of the Nevada System of Higher Education, on Behalf of the University of Nevada,
    Inventors: Claus Tittiger, Rubi Figueroa-Teran, Gary J. Blomquist
  • Publication number: 20130224800
    Abstract: The invention relates to alpha amylases and to polynucleotides encoding the alpha amylases. In addition methods of designing new alpha amylases and methods of use thereof are also provided. The alpha amylases have increased activity and stability at acidic, neutral and alkaline pH and increased temperature.
    Type: Application
    Filed: November 6, 2012
    Publication date: August 29, 2013
    Applicant: VERENIUM CORPORATION
    Inventor: Verenium Corporation
  • Publication number: 20130217886
    Abstract: The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides a more efficient route for preparing the enone intermediate.
    Type: Application
    Filed: September 14, 2012
    Publication date: August 22, 2013
    Applicant: President and Fellows of Harvard College
    Inventors: Andrew G. Myers, Jason D. Brubaker
  • Publication number: 20130150251
    Abstract: The present invention relates to compositions and methods useful for analyzing lariat RNA, which plays a role in the regulation of gene expression. A sample of RNA is specifically treated to remove linear mRNA and enrich for lariat RNA. The enriched lariat RNA sample may be analyzed further to identify introns, branch point sequences, alternative splicing patters, and gene transcription levels. The enriched lariat RNA sample may also be exploited as a detection or compound screening tool, as well as other uses.
    Type: Application
    Filed: October 29, 2012
    Publication date: June 13, 2013
    Applicant: The Curators of the University of Missouri
    Inventor: The Curators of the University of Missouri
  • Publication number: 20130122574
    Abstract: The present invention pertains to method for purifying at least a target nucleic acid from a sample, said method comprising at least the following steps: a) incubating the sample with at least one protein-degrading compound; b) binding the target nucleic acid to a solid phase; c) eluting the target nucleic acid from the solid phase; d) incubating the eluted target nucleic acid with at least one protein-degrading compound; e) binding the target nucleic acid again to a solid phase; f) optionally eluting the bound target nucleic acid from the solid phase. It was surprisingly found that performing a second protein digestion step after the target nucleic acid was bound and eluted from a solid phase before the nucleic acids are rebound to a solid phase is very efficient in reducing remaining protein contaminations in the isolated nucleic acid.
    Type: Application
    Filed: July 15, 2011
    Publication date: May 16, 2013
    Applicant: Qiagen Strasse 1
    Inventors: Thorsten Voss, Ralf Wyrich
  • Publication number: 20130095535
    Abstract: The present invention is concerned with a process of preparing (R)-lacosamide. The process comprises providing an (R,S)-lacosamide precursor and contacting the same with at least an enzyme in the presence of a solvent. The enzyme either stereoselectively hydrolyzes or acetylates an (R)- or (S)-enantiomer of the (R,S)-lacosamide precursor. The process further comprises where appropriate also concurrently, or successively, employing one or more reagents capable of converting the hydrolysed or acetylated (R)- or (S)-enantiomer to (R)-lacosamide.
    Type: Application
    Filed: June 15, 2011
    Publication date: April 18, 2013
    Applicant: MEDICHEM, S.A.
    Inventors: Jordi Bosch i Lladó, Ernesto Durán López
  • Publication number: 20130078685
    Abstract: The invention relates to a method for the ozonolysis of unsaturated fatty acids and derivatives thereof, comprising a) ozonolysis of a fatty acid or of a derivative thereof in an organic phase comprising an organic solvent, and b) contacting the organic phase with an aqueous phase comprising catalase and preferably a buffer, where the fatty acid or the derivative thereof has a linear chain having at least eight carbon atoms, and the use of catalase for removing reactive oxygen species from a reaction mixture comprising ozonolysis products of an unsaturated fatty acid.
    Type: Application
    Filed: September 21, 2012
    Publication date: March 28, 2013
    Applicant: Evonik Degussa GmbH
    Inventor: Evonik Degussa GmbH
  • Patent number: 8389248
    Abstract: Providing 1- or 6-deoxy products corresponding to all of aldohexoses, ketohexoses and sugar alcohols, as based on Deoxy-Izumoring, as well as a method for systematically producing those products. A method for producing deoxyketohexose and a derivative thereof using a deoxyketohexose isomerase derived from Pseudomonas cichorii ST-24 (FERM BP-2736), comprising epimerizing 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose at position 3 to produce the individually corresponding 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose as an intended product.
    Type: Grant
    Filed: November 20, 2007
    Date of Patent: March 5, 2013
    Assignees: National University Corporation Kagawa University, Rare Sugar Production Technical Research Laboratories, LLC., Hayashibara Co., Ltd., Matsutani Chemical Industry Co., Ltd.
    Inventors: Ken Izumori, Masaaki Tokuda, George Fleet, Yoshio Tsujisaka, Kei Takeshita, Keiji Tsusaki, Kazuhiro Okuma
  • Patent number: 8334132
    Abstract: According to the present invention, by using 4-halogeno-3-hydroxybutanamide as a substrate in quaternary amination reaction with trialkylamine which is an important step in betaine (such as carnitine) preparation processes, it becomes possible to reduce the production of crotonic acid derivatives (the major by-product) greatly compared to conventional processes. Consequently, it becomes possible to prepare a betaine, such as carnitine, at a high yield.
    Type: Grant
    Filed: November 9, 2007
    Date of Patent: December 18, 2012
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kosuke Oishi, Eiji Sato, Hiroyuki Mori, Akira Yoshioka
  • Patent number: 8252564
    Abstract: The present invention relates to a novel Burkholderia multivorans, an amidase produced from the same, and a method for optical resolution of a racemic mixture using the same, and more particularly to a strain Burkholderia multivorans LG 31-3, an amidase having stereoselective substrate specificity, and a method for optical resolution of a racemic mixture using the same. The amidase produced from the novel Burkholderia multivorans LG 31-3 (KCTC 10920BP) according to the present invention can be useful to produce single enantiomer at a high optical purity since the racemic mixture may be easily optically resolved under enzyme reaction conditions of room temperature and normal pressure.
    Type: Grant
    Filed: April 5, 2007
    Date of Patent: August 28, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Oh-Jin Park, Sang-Hyun Lee
  • Publication number: 20120213888
    Abstract: The invention relates to a DNA sequence, which codes for a polypeptide having phospholipase activity essentially without lipase activity, characterized in that the DNA sequence is selected from a) DNA sequences that comprise a nucleotide sequence according to SEQ ID NO: 1, b) DNA sequences that comprise the coding sequence according to SEQ ID NO: 1, c) DNA sequences that code for the protein sequence according to SEQ ID NO: 2, d) DNA sequences that are coded for by the plasmid pPL3940-Topo2.5 with the restriction map according to FIG.
    Type: Application
    Filed: October 27, 2010
    Publication date: August 23, 2012
    Applicant: AB ENZYMES GMBH
    Inventors: Khanh Quoc Nguyen, Kornelia Titze, Tatiana Schwarz, Silvia Paladino, Volker Marschner, Patrick Lorenz
  • Publication number: 20120214168
    Abstract: A method is provided for purifying nucleic acid from a sample in a microfluidic device. The method can be used to purify nucleic acids from any source known in the art that comprises nucleic acids, such as prokaryotic or eukaryotic organisms, viruses, cell, tissues, organs, etc. In a specific example, the tissue is whole blood. The method for purifying nucleic acid may run fully automated in the microfluidic device.
    Type: Application
    Filed: February 21, 2012
    Publication date: August 23, 2012
    Applicant: RHEONIX, INC.
    Inventors: Lincoln C. Young, Peng Zhou, Gwendolyn Spizz, Rubina Yasmin
  • Publication number: 20120156721
    Abstract: This invention provides novel chemically modified mutant serine hydrolases that catalyze a transamidation and/or a transpeptidation and/or a transesterification reaction. The modified serine hydrolases have one or more amino acid residues in a subsite replaced with a cysteine, wherein the cysteine is modified by replacing the thiol hydrogen in the cysteine with a substituent group providing a thiol side chain comprising a moiety selected from the group consisting of a polar aromatic substituent, an alkyl amino group with a positive charge, and a glycoside. In particularly preferred embodiments, the substitutents include an oxazolidinone, a C1 to C15 alkyl amino group with a positive charge, or a glycoside.
    Type: Application
    Filed: February 24, 2012
    Publication date: June 21, 2012
    Applicant: The Governing Council of the University of Toronto
    Inventors: John Bryan Jones, Michael Dickman, Richard C. Lloyd
  • Patent number: 8198069
    Abstract: A process for the production of an optically enriched tertiary alcohol of the formula (2a) or (2b), by reacting an epoxide of the formula (1) with a nucleophilic agent Nu in the presence of halohydrin dehalogenase.
    Type: Grant
    Filed: December 13, 2006
    Date of Patent: June 12, 2012
    Assignee: BASF SE
    Inventors: Bernhard Hauer, Dick B. Janssen, Maja Majeric-Elenkov
  • Publication number: 20120142939
    Abstract: The present invention relates to a process for the preparation of intermediates useful in the synthesis of [1[S(R)],2?,4?]-4-cyclohexyl-1-[[[2-methyl-1-oxypropoxy)propoxy](4-phenylbutyl phosphinyl]acetyl]L-proline, and the synthesis thereof, in particular as sodium salt (fosinopril sodium).
    Type: Application
    Filed: November 1, 2011
    Publication date: June 7, 2012
    Applicant: DIPHARMA FRANCIS S.r.l.
    Inventors: Pietro ALLEGRINI, Emanuele ATTOLINO, Alessandro DE MARCO, Fausto GORASSINI, Mario MICHIELETTI
  • Publication number: 20120135441
    Abstract: Preparation and isolation of amino vinyl cyclopropane carboxylic acid derivatives and salts thereof, methods of resolving enantiomers, and methods of identifying compositions and/or enzymes that are capable of resolving racemic or partially enantiomerically enriched mixtures.
    Type: Application
    Filed: January 2, 2012
    Publication date: May 31, 2012
    Applicants: DR. REDDY'S LABORATORIES, INC., DR. REDDY'S LABORATORIES LTD.
    Inventors: Ian N. Taylor, Michael C. Lloyd, Adrian Heseltine
  • Publication number: 20120100581
    Abstract: The invention provides novel polypeptides having phospholipase activity, including, e.g., phospholipase A, B, C and D activity, patatin activity, phosphatidic acid phosphatases (PAP)) and/or lipid acyl hydrolase (LAH) activity, nucleic acids encoding them and antibodies that bind to them. Industrial methods, e.g., oil degumming, and products comprising use of these phospholipases are also provided.
    Type: Application
    Filed: April 20, 2011
    Publication date: April 26, 2012
    Applicant: VERENIUM CORPORATION
    Inventors: SVETLANA GRAMATIKOVA, GEOFF HAZLEWOOD, DAVID LAM, NELSON R. BARTON, BLAKE G. STURGIS, DAN E. ROBERTSON, JINCAI LI, JOEL A. KREPS, RODERICK JAMES FIELDING, ROBERT C. BROWN, AMIT VASAVADA, XUQIU TAN, ADRIAN BADILLO, WILHELMUS P. VAN HOEK, GISELLE JANSSEN, CHARLES ISAAC, MARK J. BURK
  • Patent number: 8158406
    Abstract: The present invention relates to a process for the enantioselective enzymatic reduction of keto compounds, in particular of 4-halo-3-oxobutyric acid esters, to the corresponding R-alcohols or S-4-halo-3-hydroxybutyric acid esters, respectively, using an R-specific oxidoreductase in the presence of a cofactor.
    Type: Grant
    Filed: February 21, 2006
    Date of Patent: April 17, 2012
    Assignee: IEP GmbH
    Inventors: Antje Gupta, Maria Bobkova, Anke Tschentscher
  • Patent number: 8153416
    Abstract: There is provided a process for manufacture of optically-active, 2-(acyloxymethyl)-1,3-oxathiolanes of Formula I comprising a preparation of a racemic compound and an enzyme-catalyzed kinetic resolution of the enantiomers. The invention may further provide for the esterification and racemization of the by-product of the enzymatic reaction. In this manner, 2(R)-(benzoyloxymethyl)-1,3-oxathiolane is prepared as a useful intermediate for manufacture of the anti-HIV drug Apricitabine.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: April 10, 2012
    Assignee: Thesis Chemistry, LLC
    Inventor: John R. Peterson
  • Patent number: 8143052
    Abstract: The present invention discloses a process for preparing an optically active (S or R)-?-amino acid represented by the formula (II): wherein R represents an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aralkyl group, heteroarylalkyl group, aryl group or heteroaryl group, each of which may have a substituent(s), and * represents an asymmetric carbon atom, and an optically active (R or S)-?-amino acid ester represented by the formula (III): wherein R1 represents an alkyl group which may have a substituent(s), and * represents an asymmetric carbon atom, provided that it has an opposite absolute configuration to that of the compound of the formula (II), which comprises selectively reacting water with one of enantiomers of an ?-amino acid ester which is a racemic mixture and represented by the formula (I): wherein R and R1 have the same meanings as defined above, in the presence of a lipase or a protease in an organic solvent.
    Type: Grant
    Filed: August 25, 2006
    Date of Patent: March 27, 2012
    Assignee: UBE Industries, Ltd.
    Inventors: Yasuhito Yamamoto, Hiroyuki Miyata, Tadayoshi Konegawa
  • Publication number: 20120064611
    Abstract: A process for producing a compound which is (3R)-hydroxybutyl(3R)-hydroxybutyrate of formula (I) which process comprises submitting, to enantioselective reduction, a compound of the following formula (II), (III) or (IV).
    Type: Application
    Filed: April 16, 2009
    Publication date: March 15, 2012
    Inventors: Jeremy Robertson, Kieran Clarke, Richard Lewis Veech
  • Publication number: 20120064601
    Abstract: Described herein are composite materials and methods of using them for the separation or purification of enantiomers. In certain embodiments, the composite material comprises a support member, comprising a plurality of pores extending through the support member; and a macroporous cross-linked gel, comprising a plurality of macropores, and a plurality of pendant chiral moieties. In certain embodiments, the composite materials may be used in the separation or purification of a chiral small molecule.
    Type: Application
    Filed: September 13, 2011
    Publication date: March 15, 2012
    Inventors: Elena N. Komkova, Amro Ragheb, Charles H. Honeyman
  • Patent number: 8133717
    Abstract: A process is described to prepare a single enantiomer of an amino acid from its opposite enantiomer or from a racemic mixture, using an oxidase biocatalyst and a supported metal catalyst in separate, sequential reactions in water. The process can be operated in batch or continuous mode.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: March 13, 2012
    Assignee: Richmond Chemical Corporation
    Inventors: Ian Victor James Archer, Ian Fotheringham, Rueben Carr, Susan Alison Arnold
  • Patent number: 8129152
    Abstract: Immobilization of Candida rugosa lipase on a carrier selected from the group consisting of macroporous adsorbent resin of the acrylic type, synthetic epoxy activated resin and Mg—Al-hydrotalcite enhances its enantioselectivity by six to seven folds. The immobilized Candida rugosa lipase is suitable for use in resolution of racemic alcohols and/or carboxylic acids, particularly in resolution of racemic menthol or production of menthyl esters.
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: March 6, 2012
    Assignee: Universiti Putra Malaysia
    Inventors: Siti Salhah Othman, Mahiran Basri, Halila Jasmani, Mohd. Zobir Hussein, Mohd. Basyaruddin Abd. Rahman, Abu Bakar Salleh, Raja Noor Zaliha Abd. Rahman
  • Patent number: 8129173
    Abstract: Provided is a method of selectively enzymatically esterifying or selectively enzymatically solvolyzing epimers of analogs of vitamin D having a stereogenic center at C-24 that has a free or esterified OH group. The metod can be used, for example, for separating mixed epimers of the vitamin D analog.
    Type: Grant
    Filed: January 9, 2003
    Date of Patent: March 6, 2012
    Assignee: Teva Pharmaceutical Industries Ltd.
    Inventors: Evgeny Shapiro, Ayelet Fishman, Reinhard Effenberger, Asher Maymon, Anchel Schwartz
  • Patent number: 8119389
    Abstract: The present invention relates to a process for preparing (2R,3S)-1-halo-2-hydroxy-3-(protected)amino-4-substituted butane comprising contacting a mutagenized Rhodococcus erythropolis having ATCC deposit no. PTA-6648 with (3S)-1-halo-2-oxo-3-(protected)amino-4-substituted butane substrate. The present invention also relates to a process comprising mixing (2R,3S)-1-halo-2-hydroxy-3-(protected)amino-4-substituted butane with at least one base in the presence of at least one solvent to produce a reaction mixture containing (2R,3S)-1,2-epoxy-3-(protected)amino-4-substituted butane. The present invention further relates to a process comprising crystallizing the (2R,3S)-1,2-epoxy-3-(protected)amino-4-substituted butane out of the reaction mixture by concurrently adding water and the reaction mixture together. The present invention is also directed to a mutagenized Rhodococcus erythropolis having ATCC deposit no. PTA-6648.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: February 21, 2012
    Assignee: Bristol-Myers Squibb Company
    Inventors: Nigel Ian Bowers, Paul M. Skonezny, Gregory L. Stein, Thomas Franceschini, Shu-Jen Chiang, Wendy L. Anderson, Li You, Zizhuo Xing
  • Publication number: 20120028340
    Abstract: A process for synthesis of 4S-phenyl-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3 oxazolidin 2-one comprising resolution of 4S-phenyl-3-[(5RS)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3 oxazolidin 2-one by selective esterification of 4S-phenyl-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3 oxazolidin 2-one using appropriate esterification reagent in an organic solvent in presence of Lipase enzyme at a temperature ranging from 0° to 100° C., and further isolation.
    Type: Application
    Filed: April 5, 2010
    Publication date: February 2, 2012
    Inventors: Piyush Suresh Lathi, Bhairab Nath Roy, Girij Pal Singh, Dhananjai Shrivastava
  • Patent number: 8076107
    Abstract: Methods and materials for the production of the high intensity sweetener, monatin, in stereoisomerically-pure or stereoisomerically-enriched form are disclosed. For example, methods using stereoisoselective hydrolysis and separation of a monatin-derived lactone ester are disclosed.
    Type: Grant
    Filed: October 1, 2007
    Date of Patent: December 13, 2011
    Assignee: Cargill, Incorporated
    Inventors: Subash Buddoo, Amanda Louise Rousseau, Dean Brady, James Lalonde, Yiming Yao, Yifong Wang
  • Patent number: 8067640
    Abstract: The present invention relates to a novel method for the preparation of diol intermediates having the formula (II) and/or the opposite enantiomer of an acylated diol having the formula (IV) useful for the preparation of escitalopram involving selective enzymatic acylation or deacylation.
    Type: Grant
    Filed: May 17, 2010
    Date of Patent: November 29, 2011
    Assignee: H. Lundbeck A/S
    Inventors: Naoki Taoka, Takahisa Kato, Shogo Yamamoto, Takashi Yoshida, Toshihiro Takeda, Yasuyoshi Ueda, Hans Petersen, Robert Dancer, Haleh Ahmadian, Lars O. Lyngso
  • Patent number: 8017378
    Abstract: Disclosed is a method for production of an optically active biphenylalanine compound represented by the formula (2): (wherein, R2 is a protective group of an amino group, and R3 and R4 are each independently a hydrogen atom, etc.) or a salt thereof and an optically active biphenylalanine ester compound represented by the formula (3): (wherein, R1 is an alkyl group, etc.) wherein the method comprises hydrolyzing a biphenylalanine ester compound represented by the formula (1): with a protease produced by a microorganism belonging to Bacillus sp. in the presence of at least one alkali selected from an alkali metal hydroxide and an alkaline earth metal hydroxide.
    Type: Grant
    Filed: January 15, 2007
    Date of Patent: September 13, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Sugi, Masahide Tanaka, Yoshihiro Kawada, Daisuke Sasayama
  • Patent number: 8008062
    Abstract: A method for preparing optically active methyl 4-(1-ammoniumethyl)benzoate sulfate by reacting racemic methyl 4-(1-aminoethyl)benzoate with an acylating agent in the presence of a lipase to give methyl 4-(1-aminoethyl)benzoate and subsequently precipitating methyl 4-(1-ammoniumethyl)benzoate sulfate by adding sulfuric acid.
    Type: Grant
    Filed: December 19, 2006
    Date of Patent: August 30, 2011
    Assignee: BASF SE
    Inventors: Klaus Ditrich, Harald Winsel, Dominique Moulin
  • Patent number: 7993904
    Abstract: A process for the production of an optically enriched oxazolidinone of the formula (2a) or (2b), by reacting an epoxide of the formula (1) with cyanate in the presence of halo-hydrin dehalogenase.
    Type: Grant
    Filed: February 28, 2007
    Date of Patent: August 9, 2011
    Assignee: BASF SE
    Inventors: Bernhard Hauer, Dirk Barend Janssen, Maja Majeric Elenkov
  • Patent number: 7972836
    Abstract: The present invention relates to a method for preparing an optically active 4-hydroxy-1,2,3,4-tetrahydroquinoline compound [I], which comprises the steps of: treating a racemic 4-hydroxy-1,2,3,4-tetrahydroquinoline compound represented by general formula [I]: [wherein R1 represents a hydrogen atom or a protecting group for amino group.] with an enzyme having an ability of selectively or preferentially acylating one enantiomer of the racemic compound [I] in the presence of an acyl donor; and if necessary, subjecting the reaction product to solvolysis.
    Type: Grant
    Filed: October 4, 2006
    Date of Patent: July 5, 2011
    Assignee: Mitsubishi Tanabe Pharma Corporation
    Inventors: Masaki Okamoto, Akira Sakuragi, Muneki Kishida, Yoshikazu Mori