Resolution Of Optical Isomers Or Purification Of Organic Compounds Or Composition Containing Same Patents (Class 435/280)
-
Patent number: 11814664Abstract: Provided herein are non-naturally occurring microbial organisms having a pathway for production of (3R)-hydroxybutyl (3R)-hydroxybutyrate, wherein the organism can further include a (R)-1,3-butanediol pathway, a (3R)-hydroxybutyrate pathway, a (3R)-hydroxybutyryl-CoA pathway, an acetoacetate pathway, an acetoacetyl-CoA pathway, a (3R)-hydroxybutyl-ACP pathway, or an acetoacetyl-ACP pathway. Additionally provided are methods and processes for producing and isolating (3R)-hydroxybutyl (3R)-hydroxybutyrate using the microbial organisms, and various compositions having the (3R)-hydroxybutyl (3R)-hydroxybutyrate. Still further provided are methods of treating or preventing a disease, disorder or condition using the (3R)-hydroxybutyl (3R)-hydroxybutyrate produced by the microbial organisms of the invention.Type: GrantFiled: May 23, 2014Date of Patent: November 14, 2023Assignee: Genomatica, Inc.Inventors: Benjamin Adelstein, Robin E. Osterhout, Mark J. Burk
-
Patent number: 10508070Abstract: 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: GrantFiled: December 27, 2018Date of Patent: December 17, 2019Assignee: SHANGHAI SHINE HIGH INTERNATIONAL TRADE CO., LTD.Inventor: Yanwang Hu
-
Patent number: 9435817Abstract: 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: GrantFiled: August 14, 2012Date of Patent: September 6, 2016Assignee: Randox Laboratories LimitedInventors: Elouard Benchikh, Stephen Peter Fitzgerald, Paul John Innocenzi, Philip Andrew Lowry, Ivan Robert McConnell
-
Patent number: 9074228Abstract: 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: GrantFiled: February 13, 2007Date of Patent: July 7, 2015Assignee: LONZA AGInventors: Karen Robins, Uwe Bornscheuer, Matthias Höhne
-
Patent number: 9034613Abstract: 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: GrantFiled: April 16, 2009Date of Patent: May 19, 2015Assignees: ISIS Innovation Limited, The United States of America, as Represented by the Secretary, Department of Health & Human ServicesInventors: Jeremy Robertson, Kieran Clarke, Richard Lewis Veech
-
Patent number: 9005957Abstract: 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: GrantFiled: October 20, 2009Date of Patent: April 14, 2015Assignee: CJ Cheiljedang CorporationInventors: Kuk-Ki Hong, Jin-Su Chung, Sooan Shin, Hyeran Park, Jaehyun Jo
-
Patent number: 8969068Abstract: 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: GrantFiled: April 30, 2009Date of Patent: March 3, 2015Assignee: Gradalis, Inc.Inventor: Nancy Smyth Templeton
-
Publication number: 20150037852Abstract: 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: ApplicationFiled: August 4, 2014Publication date: February 5, 2015Inventors: Lu-Kwang Ju, Majid Hosseini
-
Patent number: 8945890Abstract: 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: GrantFiled: February 25, 2013Date of Patent: February 3, 2015Assignee: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada, RenoInventors: Claus Tittiger, Rubi Figueroa-Teran, Gary J. Blomquist
-
Patent number: 8932835Abstract: 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: GrantFiled: September 22, 2008Date of Patent: January 13, 2015Assignee: IEP GmbHInventors: Antje Gupta, Maria Bobkova, Anke Tschentscher
-
Patent number: 8921080Abstract: 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: GrantFiled: April 26, 2010Date of Patent: December 30, 2014Assignee: DSM IP Assets B.V.Inventors: Martin Kietzmann, Harald Pichler, Helmut Schwab, Amin El-Heliebi, Christine Winkler, Andreas Braun
-
Publication number: 20140212957Abstract: 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: ApplicationFiled: June 22, 2012Publication date: July 31, 2014Applicant: THYSSENKRUPP INDUSTRIAL SOLUTIONS GMBHInventors: Wolfgang Tietz, Joachim Schulze, Armin Boerner, Ivan Shuklov, Klaus Kuehlein
-
Publication number: 20140186925Abstract: 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: ApplicationFiled: July 5, 2012Publication date: July 3, 2014Applicants: IZUMORING CO., LTD., MATSUTANI CHEMICAL INDUSTRY CO., LTD.Inventors: Ken Izumori, Pushpa Kiran Gullapalli, Tomoya Shintani, Ryo Kikkawa
-
Publication number: 20140154784Abstract: 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: ApplicationFiled: December 3, 2012Publication date: June 5, 2014Inventor: Gregory van Buskirk
-
Patent number: 8647857Abstract: 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: GrantFiled: April 30, 2009Date of Patent: February 11, 2014Assignee: Gradalis, Inc.Inventor: Nancy Smyth Templeton
-
Publication number: 20140011224Abstract: 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: ApplicationFiled: August 27, 2012Publication date: January 9, 2014Applicant: Council of Scientific & Industrial ResearchInventors: Ahmed Kamal, Rohini Khanna, Chityal Ganesh Kumar, Anver Basha Shaik, Matam Shiva Kumar
-
Patent number: 8546114Abstract: 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: GrantFiled: January 18, 2006Date of Patent: October 1, 2013Assignee: Chirogate International Inc.Inventors: Yu-Chih Yeh, Ming-Kun Hsu, Shih-Yi Wei
-
Patent number: 8530213Abstract: 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: GrantFiled: December 2, 2010Date of Patent: September 10, 2013Assignees: Georgia Tech Research Corporation, Emory UniversityInventors: Andreas Bommarius, Bettina Bommarius, Jun-Ichiro Hirano, Vaijayanthi Thangavel, Jonathan Taejoo Park
-
Publication number: 20130230878Abstract: 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: ApplicationFiled: February 25, 2013Publication date: September 5, 2013Applicant: 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: 20130224800Abstract: 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: ApplicationFiled: November 6, 2012Publication date: August 29, 2013Applicant: VERENIUM CORPORATIONInventor: Verenium Corporation
-
Publication number: 20130217886Abstract: 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: ApplicationFiled: September 14, 2012Publication date: August 22, 2013Applicant: President and Fellows of Harvard CollegeInventors: Andrew G. Myers, Jason D. Brubaker
-
Publication number: 20130150251Abstract: 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: ApplicationFiled: October 29, 2012Publication date: June 13, 2013Applicant: The Curators of the University of MissouriInventor: The Curators of the University of Missouri
-
Publication number: 20130122574Abstract: 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: ApplicationFiled: July 15, 2011Publication date: May 16, 2013Applicant: Qiagen Strasse 1Inventors: Thorsten Voss, Ralf Wyrich
-
Publication number: 20130095535Abstract: 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: ApplicationFiled: June 15, 2011Publication date: April 18, 2013Applicant: MEDICHEM, S.A.Inventors: Jordi Bosch i Lladó, Ernesto Durán López
-
Publication number: 20130078685Abstract: 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: ApplicationFiled: September 21, 2012Publication date: March 28, 2013Applicant: Evonik Degussa GmbHInventor: Evonik Degussa GmbH
-
Patent number: 8389248Abstract: 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: GrantFiled: November 20, 2007Date of Patent: March 5, 2013Assignees: 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: 8334132Abstract: 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: GrantFiled: November 9, 2007Date of Patent: December 18, 2012Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kosuke Oishi, Eiji Sato, Hiroyuki Mori, Akira Yoshioka
-
Patent number: 8252564Abstract: 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: GrantFiled: April 5, 2007Date of Patent: August 28, 2012Assignee: LG Chem, Ltd.Inventors: Oh-Jin Park, Sang-Hyun Lee
-
Publication number: 20120213888Abstract: 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: ApplicationFiled: October 27, 2010Publication date: August 23, 2012Applicant: AB ENZYMES GMBHInventors: Khanh Quoc Nguyen, Kornelia Titze, Tatiana Schwarz, Silvia Paladino, Volker Marschner, Patrick Lorenz
-
Publication number: 20120214168Abstract: 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: ApplicationFiled: February 21, 2012Publication date: August 23, 2012Applicant: RHEONIX, INC.Inventors: Lincoln C. Young, Peng Zhou, Gwendolyn Spizz, Rubina Yasmin
-
CHEMICALLY MODIFIED MUTANT SERINE HYDROLASES SHOW IMPROVED CATALYTIC ACTIVITY AND CHIRAL SELECTIVITY
Publication number: 20120156721Abstract: 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: ApplicationFiled: February 24, 2012Publication date: June 21, 2012Applicant: The Governing Council of the University of TorontoInventors: John Bryan Jones, Michael Dickman, Richard C. Lloyd -
Patent number: 8198069Abstract: 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: GrantFiled: December 13, 2006Date of Patent: June 12, 2012Assignee: BASF SEInventors: Bernhard Hauer, Dick B. Janssen, Maja Majeric-Elenkov
-
Publication number: 20120142939Abstract: 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: ApplicationFiled: November 1, 2011Publication date: June 7, 2012Applicant: DIPHARMA FRANCIS S.r.l.Inventors: Pietro ALLEGRINI, Emanuele ATTOLINO, Alessandro DE MARCO, Fausto GORASSINI, Mario MICHIELETTI
-
Publication number: 20120135441Abstract: 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: ApplicationFiled: January 2, 2012Publication date: May 31, 2012Applicants: DR. REDDY'S LABORATORIES, INC., DR. REDDY'S LABORATORIES LTD.Inventors: Ian N. Taylor, Michael C. Lloyd, Adrian Heseltine
-
Publication number: 20120100581Abstract: 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: ApplicationFiled: April 20, 2011Publication date: April 26, 2012Applicant: VERENIUM CORPORATIONInventors: 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: 8158406Abstract: 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: GrantFiled: February 21, 2006Date of Patent: April 17, 2012Assignee: IEP GmbHInventors: Antje Gupta, Maria Bobkova, Anke Tschentscher
-
Patent number: 8153416Abstract: 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: GrantFiled: December 10, 2009Date of Patent: April 10, 2012Assignee: Thesis Chemistry, LLCInventor: John R. Peterson
-
Patent number: 8143052Abstract: 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: GrantFiled: August 25, 2006Date of Patent: March 27, 2012Assignee: UBE Industries, Ltd.Inventors: Yasuhito Yamamoto, Hiroyuki Miyata, Tadayoshi Konegawa
-
Publication number: 20120064611Abstract: 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: ApplicationFiled: April 16, 2009Publication date: March 15, 2012Inventors: Jeremy Robertson, Kieran Clarke, Richard Lewis Veech
-
Publication number: 20120064601Abstract: 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: ApplicationFiled: September 13, 2011Publication date: March 15, 2012Inventors: Elena N. Komkova, Amro Ragheb, Charles H. Honeyman
-
Patent number: 8133717Abstract: 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: GrantFiled: December 21, 2007Date of Patent: March 13, 2012Assignee: Richmond Chemical CorporationInventors: Ian Victor James Archer, Ian Fotheringham, Rueben Carr, Susan Alison Arnold
-
Patent number: 8129173Abstract: 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: GrantFiled: January 9, 2003Date of Patent: March 6, 2012Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Evgeny Shapiro, Ayelet Fishman, Reinhard Effenberger, Asher Maymon, Anchel Schwartz
-
Patent number: 8129152Abstract: 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: GrantFiled: August 1, 2008Date of Patent: March 6, 2012Assignee: Universiti Putra MalaysiaInventors: Siti Salhah Othman, Mahiran Basri, Halila Jasmani, Mohd. Zobir Hussein, Mohd. Basyaruddin Abd. Rahman, Abu Bakar Salleh, Raja Noor Zaliha Abd. Rahman
-
Patent number: 8119389Abstract: 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: GrantFiled: July 21, 2009Date of Patent: February 21, 2012Assignee: Bristol-Myers Squibb CompanyInventors: Nigel Ian Bowers, Paul M. Skonezny, Gregory L. Stein, Thomas Franceschini, Shu-Jen Chiang, Wendy L. Anderson, Li You, Zizhuo Xing
-
Publication number: 20120028340Abstract: 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: ApplicationFiled: April 5, 2010Publication date: February 2, 2012Inventors: Piyush Suresh Lathi, Bhairab Nath Roy, Girij Pal Singh, Dhananjai Shrivastava
-
Patent number: 8076107Abstract: 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: GrantFiled: October 1, 2007Date of Patent: December 13, 2011Assignee: Cargill, IncorporatedInventors: Subash Buddoo, Amanda Louise Rousseau, Dean Brady, James Lalonde, Yiming Yao, Yifong Wang
-
Patent number: 8067640Abstract: 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: GrantFiled: May 17, 2010Date of Patent: November 29, 2011Assignee: H. Lundbeck A/SInventors: Naoki Taoka, Takahisa Kato, Shogo Yamamoto, Takashi Yoshida, Toshihiro Takeda, Yasuyoshi Ueda, Hans Petersen, Robert Dancer, Haleh Ahmadian, Lars O. Lyngso
-
Patent number: 8017378Abstract: 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: GrantFiled: January 15, 2007Date of Patent: September 13, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoshi Sugi, Masahide Tanaka, Yoshihiro Kawada, Daisuke Sasayama
-
Patent number: 8008062Abstract: 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: GrantFiled: December 19, 2006Date of Patent: August 30, 2011Assignee: BASF SEInventors: Klaus Ditrich, Harald Winsel, Dominique Moulin
-
Patent number: 7993904Abstract: 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: GrantFiled: February 28, 2007Date of Patent: August 9, 2011Assignee: BASF SEInventors: Bernhard Hauer, Dirk Barend Janssen, Maja Majeric Elenkov