Resolution Of Optical Isomers Or Purification Of Organic Compounds Or Composition Containing Same Patents (Class 435/280)
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Patent number: 7358396Abstract: A process for preparing optically active amines, a process for preparing racemic amines which can be resolved using optically active carboxylic acids or enzymes, and racemic and optically active amines and optically active amides are described.Type: GrantFiled: January 9, 2006Date of Patent: April 15, 2008Assignee: BASF AktiengesellschaftInventors: Klaus Ditrich, Wolfgang Siegel
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Patent number: 7354771Abstract: The absolute configuration of a chiral compound is determined by (i) coordinating the chiral compound to a metalloporphyrin having a carbon chain-crosslinked porphyrin dimer structure in which one of the two porphyrin rings has at least one ethyl or substituent bulkier than ethyl at at least one of the second peripheral carbon atoms from the carbon atom at the carbon chain crosslink site, and (ii) analyzing the resultant coordination compound by circular dichroism spectrophotometry to determine the absolute configuration of the asymmetric carbon based on the sign of the Cotton effect. The chiral compound has an asymmetric carbon bonded to a basic group capable of coordinating to the metal of the other porphyrin ring of the metalloporphyrin dimer or an asymmetric carbon atom adjacent to the carbon atom bonded to the basic group.Type: GrantFiled: December 4, 2000Date of Patent: April 8, 2008Assignee: Japan Science and Technology CorporationInventors: Yoshihisa Inoue, Victor Borovkov, Juha Lintuluoto
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Patent number: 7326559Abstract: The present invention provides a process for producing an optically active allene represented by formula (1): wherein R2 and R3 are different and each represents a hydrogen atom, an optionally substituted C1-20 alkyl group or an optionally substituted C6-20 aryl group, and R4 represents an acyl group, which comprises reacting an allene derivative represented by formula (2): wherein R1 represents a hydrogen atom or an optionally substituted acyl group and R2 and R3 have the same meaning as defined above, with an acylating agent having an acyl group represented by R4 when both R1s are each a hydrogen atom or with water when both R1s are each an acyl group represented by R4, in the presence of an enzyme catalyst. According to this production process, an optically active allene can be produced efficiently and enantioselectively from an allene derivative having a symmetrical structure.Type: GrantFiled: September 6, 2002Date of Patent: February 5, 2008Assignee: Japan Science and Technology AgencyInventors: Keisuke Suzuki, Takashi Matsumoto
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Patent number: 7319027Abstract: Thermostable omega-transaminases, particularly thermostable omega-transaminases which have a high reaction rate and which are tolerant to high concentrations of donor amine, can be used to enrich enantiomerically a mixture of chiral amines or to synthesize stereoselectively one of a pair of chiral amines in which the amino group is bound to a non-terminal, chirally substituted, carbon atom.Type: GrantFiled: January 29, 2007Date of Patent: January 15, 2008Assignee: Cambrex Karlskoga ABInventors: Sachin Pannuri, Sanjay Venkatesh Kamat, Abraham Rogelio Martin-Garcia
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Patent number: 7276360Abstract: Thermostable omega-transaminases, particularly thermostable omega-transaminases which have a high reaction rate and which are tolerant to high concentrations of donor amine, can be used to enrich enantiomerically a mixture of chiral amines or to synthesize stereoselectively one of a pair of chiral amines in which the amino group is bound to a non-terminal, chirally substituted, carbon atom.Type: GrantFiled: January 29, 2007Date of Patent: October 2, 2007Assignee: Cambrex Kariskoga ABInventors: Sachin Pannuri, Sanjay Venkatesh Kamat, Abraham Rogelio Martin-Garcia
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Patent number: 7267969Abstract: Thermostable omega-transaminases, particularly thermostable omega-transaminases which have a high reaction rate and which are tolerant to high concentrations of donor amine, can be used to enrich enantiomerically a mixture of chiral amines or to synthesize stereoselectively one of a pair of chiral amines in which the amino group is bound to a non-terminal, chirally substituted, carbon atom.Type: GrantFiled: January 29, 2007Date of Patent: September 11, 2007Assignee: Cambrex KarlskogaInventors: Sachin Pannuri, Sanjay Venkatesh Kamat, Abraham Rogelio Martin Garcia
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Patent number: 7264960Abstract: Glycol ether acetates, and in particular propylene glycol alkyl (or aryl) ether acetates, can be resolved enzymatically by enantioselective hydrolysis with a hydrolase at high concentrations of substrates; in some embodiments, the hydrolase is a lipase. Glycol ethers, and in particular propylene glycol alkyl (or aryl) ethers, can be resolved enzymatically by enantioselective transesterification with a hydrolase, in the presence of an acyl donor, at high concentrations of substrates; in some embodiments, the hydrolase is a lipase.Type: GrantFiled: March 21, 2003Date of Patent: September 4, 2007Assignee: Dow Global Technologies Inc.Inventors: Sol M. Resnick, Felipe A. Donate, Timothy C. Frank, Thomas C. Thyne, Paul Foley
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Patent number: 7264952Abstract: Thermostable omega-transaminases, particularly thermostable omega-transaminases which have a high reaction rate and which are tolerant to high concentrations of donor amine, can be used to enrich enantiomerically a mixture of chiral amines or to synthesize stereoselectively one of a pair of chiral amines in which the amino group is bound to a non-terminal, chirally substituted, carbon atom.Type: GrantFiled: January 29, 2007Date of Patent: September 4, 2007Assignee: Cambrex KariskogaInventors: Sachin Pannuri, Sanjay Venkatesh Kamat, Abraham Rogelio Martin-Garcia
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Patent number: 7247468Abstract: A method for producing an optically active compound comprising: a first step of culturing a microorganism capable of assimilating either the R-isomer or the S-isomer of a compound represented by Formula (1): wherein R is a methyl, ethyl, propyl, chloromethyl, or hydroxyethyl group, in a culture medium whose Ca2+ concentration at the beginning of culturing is controlled and which contains a racemic mixture of the compound as a carbon source; and a second step of recovering the optically active compound remaining in the culture broth.Type: GrantFiled: April 29, 2005Date of Patent: July 24, 2007Assignee: Daiso Co., Ltd.Inventors: Toshio Suzuki, Kouji Nishikawa, Atsushi Nakagawa
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Patent number: 7247460Abstract: Thermostable omega-transaminases, particularly thermostable omega-transaminases which have a high reaction rate and which are tolerant to high concentrations of donor amine, can be used to enrich enantiomerically a mixture of chiral amines or to synthesize stereoselectively one of a pair of chiral amines in which the amino group is bound to a non-terminal, chirally substituted, carbon atom.Type: GrantFiled: January 29, 2007Date of Patent: July 24, 2007Assignee: Cambrex KariskogaInventors: Sachin Pannuri, Sanjay Venkatesh Kamat, Abraham Rogelio Martin-Garcia
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Patent number: 7235399Abstract: The present invention provides a method for obtaining optically active 3-chloro-2-methyl-1,2-propanediol, the method comprising: a first step of letting at least one kind of microorganism or processed product thereof having an ability to leave untouched (R)-3-chloro-2-methyl-1,2-propanediol or (S)-3-chloro-2-methyl-1,2-propanediol in the presence of an enantiomeric 3-chloro-2-methyl-1,2-propanediol mixture act on an enantiomeric 3-chloro-2-methyl-1,2-propanediol mixture; and a second step of recovering the untouched optically active 3-chloro-2-methyl-1,2-propanediol.Type: GrantFiled: January 4, 2005Date of Patent: June 26, 2007Assignee: Daiso Co., Ltd.Inventors: Kouji Nishikawa, Toshio Suzuki, Atsushi Nakagawa, Keiko Suzuki, Satoshi Nakayama
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Patent number: 7220562Abstract: A method has been developed to prepare (E)- and (Z)-2-methyl-2-butenoic acids (2M2BA) from a mixture of (E,Z)-2-methyl-2-butenenitriles (2M2BN) by the regioselective hydrolysis of (E)-2M2BN to (E)-2-methyl-2-butenoic acid (2M2BA) using enzyme catalysts having either a nitrilase activity or a combination of nitrile hydratase and amidase activities. The method provides high yields without significant conversion of (Z)-2M2BN to (Z)-2M2BA. The regioselective hydrolysis of (E)-2M2BN to (E)-2M2BA makes possible the facile separation of (E)-2M2BA from (Z)-2M2BN or (Z)-2-methyl-2-butenamide (2M2BAm), and the subsequent conversion of (Z)-2M2BN or (Z)-2M2BAm to (Z)-2M2BA.Type: GrantFiled: January 24, 2006Date of Patent: May 22, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Michael G. Bramucci, Robert DiCosimo, Sarita Chauhan, Robert D. Fallon, John E. Gavagan, Mark S. Payne
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Patent number: 7217560Abstract: Treatment of a lactic acid ester derivative with an enzyme or the like, which has asymmetric ester-hydrolyzing ability, can specifically hydrolyze the ester moiety of an isomer existing as the pair to the racemic derivative.Type: GrantFiled: March 6, 2002Date of Patent: May 15, 2007Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Kouji Sato, Tsutomu Yagi, Kazuo Kubota, Akihiro Imura
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Patent number: 7208631Abstract: A process for producing a 2-alkylcysteinamide, which comprises hydrolysis of a 4-alkylthiazolidine-4-carboxamide represented by the general formula (2) or a salt thereof: wherein R represents a lower alkyl group having 1–4 carbon atoms; and each of R1 and R2 independently represents hydrogen or a lower alkyl group having 1–4 carbon atoms, or R1 and R2 are linked together to form an alicyclic, structure having 4–7 carbon atoms, excluding the case where both R1 and R2 are hydrogen, to give a 2-alkylcysteinamide represented by the general formula (1) or a salt thereof wherein R represents a lower alkyl group having 1–4 carbon atoms. Cells of a microorganism or treated products thereof having activity of stereoselective hydrolysis of a 2-alkyl-L-cysteinamide are allowed to act on the compound represented by the general formula (1) to yield a 2-alkyl-L-cysteine.Type: GrantFiled: April 7, 2004Date of Patent: April 24, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yasushi Higuchi, Akinori Tanaka, Ryuji Hasemi
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Patent number: 7198926Abstract: A method has been developed to prepare (E)- and (Z)-2-methyl-2-butenoic acids (2M2BA) from a mixture of (E,Z)-2-methyl-2-butenenitriles (2M2BN) by the regioselective hydrolysis of (E)-2M2BN to (E)-2-methyl-2-butenoic acid (2M2BA) using enzyme catalysts having either a nitrilase activity or a combination of nitrile hydratase and amidase activities. The method provides high yields without significant conversion of (Z)-2M2BN to (Z)-2M2BA. The regioselective hydrolysis of (E)-2M2BN to (E)-2M2BA makes possible the facile separation of (E)-2M2BA from (Z)-2M2BN or (Z)-2-methyl-2-butenamide (2M2BAm), and the subsequent conversion of (Z)-2M2BN or (Z)-2M2BAm to (Z)-2M2BA.Type: GrantFiled: May 8, 2003Date of Patent: April 3, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Michael G. Bramucci, Robert Dicosimo, John E. Gavagan, Mark S. Payne, Robert D. Fallon, Sarita Chauhan
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Patent number: 7172885Abstract: Thermostable omega-transaminases, particularly thermostable omega-transaminases which have a high reaction rate and which are tolerant to high concentrations of donor amine, can be used to enrich enantiomerically a mixture of chiral amines or to synthesize stereoselectively one of a pair of chiral amines in which the amino group is bound to a non-terminal, chirally substituted, carbon atom.Type: GrantFiled: December 7, 2005Date of Patent: February 6, 2007Assignee: Cambrex North Brunswick, Inc.Inventors: Sachin Pannuri, Sanjay Venkatesh Kamat, Abraham Rogelio Martin Garcia
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Patent number: 7169591Abstract: A method for converting alkenes into epoxides and, particularly, to convert alkenes into enantio-specific epoxides by the use of enzymes which may be in their naturally-occuring (native) form or in mutated form, such as a native or mutated non-haem diiron-containing monooxygenase, and novel compounds produced thereby.Type: GrantFiled: May 26, 2000Date of Patent: January 30, 2007Assignee: Shaw Environmental & Infrastructure, Inc.Inventors: Robert J. Steffan, Kevin R. McClay
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Patent number: 7148055Abstract: The present invention provides a method for preparing optically active 3-hydroxypentanenitrile with high yield. Optically active 3-hydroxypentanenitrile is prepared by stereoselectively reducing 3-ketopentanenitrile by action of an enzyme, which asymmetrically reduces 3-ketopentanenitrile to optically active 3-hydroxypentanenitrile. Also, alkali metal salt of 3-ketopentanenitrile, which is a stable compound without problems regarding storage, can be efficiently obtained.Type: GrantFiled: October 3, 2002Date of Patent: December 12, 2006Assignee: Kaneka CorporationInventors: Shigeru Kawano, Yoshihiko Yasohara
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Patent number: 7141412Abstract: A process for the preparation of optically active 3-hydroxypyrrolidine or N-substituted 3-hydroxypyrrolidines, wherein an oxygen atom is inserted stereoselectively into the corresponding pyrrolidines, respectively, by use of a bacterium having hydroxylation activity, or a prokaryotic host-organism having the gene(s) necessary for the hydroxylation, or an enzyme having hydroxylation activity derived therefrom. The bacterium may be selected from strains having alkane hydroxylases, strains degrading alkanes or mono-alicyclic compounds, or strains from the genera Pseudomonas, Mycobacterium, Corynebacterium, Nocardia, Sphingomonas, Gordona, Rhodococcus, Bacillus, Streptomyces; Sebekia and Methylococcus.Type: GrantFiled: February 24, 2003Date of Patent: November 28, 2006Assignee: Eidgenossische Technische Hochschule ZurichInventors: Zhi Li, Bernard Witholt
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Patent number: 7135328Abstract: The invention relates to a process for the production of (R)- or (S)-8-chloro-6-hydroxyoctanoic acid alkyl esters of the general formula (R)-II or (S)-II, in which R means C1-4 alkyl, from 8-chloro-6-oxo-octanoic acid alkyl esters of the general formula I, in which R has the above meaning. The desired enantiomers are produced biocatalytically in an enantioselective reduction, wherein as desired the strains Mucor racemosus are used for (S)-II compounds and Geotrichum candidum for (R)-II compounds. The resultant esters may, in known manner, be converted stereospecifically into (R)-?-lipoic acid.Type: GrantFiled: July 20, 2001Date of Patent: November 14, 2006Assignee: Viatris GmbH & Co. KGInventors: Matthias Olbrich, Rainer Gewald
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Patent number: 7115412Abstract: Disclosed are a process for preparation of an optically active 7-substituted 3-(2-aminopropyl)indole compound and an intermediate therefor. In the above preparation process, 7-substituted indole is reacted with L- or DL-serine in the presence of a tryptophan-synthesizing enzyme originating in microorganisms to form corresponding 7-substituted L-tryptophan, and it is subjected, if necessary, to reduction, protection, exchange and elimination.Type: GrantFiled: March 30, 2001Date of Patent: October 3, 2006Assignees: Mercian Corporation, Dainippon Pharmaceutical Co., Ltd.Inventors: Takao Narita, Kunihiro Toyoda, Yoichiro Hirose, Toshio Tsuchida, Shiro Kato, Hiroshi Harada, Akihito Fujii
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Patent number: 7112431Abstract: The present invention relates to a 5-substituted hydantoin racemase, which efficiently catalyzes racemization reactions at a high optimum temperature for racemization reactions, DNA coding for the racemase, and processes for producing optically active amino acids.Type: GrantFiled: June 9, 2004Date of Patent: September 26, 2006Assignee: Ajinomoto Co. Inc.Inventors: Shunichi Suzuki, Norimasa Onishi, Kenzo Yokozeki
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Patent number: 7102018Abstract: Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-[(dimethylmethylene)dioxy]-5-hydroxy-tricyclo[5.2.1.02,6]dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo[5.2.1.02,6]deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.Type: GrantFiled: February 21, 2003Date of Patent: September 5, 2006Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Kunio Ogasawara
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Patent number: 7094594Abstract: The present invention is to provide a production technology by which an optically active 2-[6-(hydroxymethyl)-1, 3-dioxan-4-yl]acetic acid derivative, which are of value as pharmaceutical intermediates, can be produced from inexpensive and readily available starting materials without using any extraordinary equipment such as an ultra-low-temperature reactor. The present invention is a production process of an optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivative which comprises reacting an enolate, prepared by permitting a base or a 0-valent metal to act on an acetic acid ester derivative with (S)-?-hydroxy-?-butyrolactone at a temperature not lower than ?30° C.Type: GrantFiled: June 5, 2001Date of Patent: August 22, 2006Assignee: Kaneka CorporationInventors: Akira Nishiyama, Miho Horikawa, Yoshihiko Yasohara, Noboru Ueyama, Kenji Inoue
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Patent number: 7091023Abstract: An esterase isolated from Aspergillus oryzae is capable of stereoselective hydrolysis of chiral esters and also has arylesterase activity (EC 3.1.1.2) and feruloyl esterase activity (EC 3.1.1.73). The esterase has only a limited homology to known amino acid sequences.Type: GrantFiled: July 19, 2001Date of Patent: August 15, 2006Assignee: Novozymes A/SInventors: Peter Rahbek Ostergaard, Carsten M. Hjort, Heinz-Josef Deussen, Magali Zundel, Soren Ebdrup, Soren Christensen, Shamkant Anant Patkar
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Patent number: 7083973Abstract: The present invention relates to a process for the stereoselective enzymatic reduction of 1-halo-2-oxo-3-(protected)amino-4-substituted-butanes utilizing certain species of Rhodococcus and Brevibacterium. The product 1-halo-2-hydroxy-3-(protected)amino-4-substituted-butanes, which are useful as intermediates in the synthesis of compounds that are inhibitors of ACE, renin and HIV proteases, are obtained in high yield and, particularly, in very high diastereomeric purity. The process is advantageously highly selective for the (3S,2R) enantiomer of the product.Type: GrantFiled: September 12, 2003Date of Patent: August 1, 2006Assignee: Bristol-Myers Squibb CompanyInventors: Ramesh N. Patel, Linda Chu
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Patent number: 7078225Abstract: The present invention relates to an enzyme reaction method which comprises performing an enzyme reaction, using an immobilized enzyme having a water content of 10% by weight or more as an enzyme and using an organic solvent substantially immiscible with water as a reaction solvent, under such conditions that a liquid phase forms a homogeneous system without phase separation although it is saturated with water or an aqueous buffer; a method for performing an enzyme reaction using an aldehyde compound as a substrate, which comprises removing a carboxylic acid compound contained in an aldehyde compound by subjecting the aldehyde compound to an alkaline treatment before starting the enzyme reaction; a method for performing an enzyme reaction using an aldehyde compound as a substrate, which comprises reducing a carboxylic acid compound content in the aldehyde compound to 0.Type: GrantFiled: June 1, 2001Date of Patent: July 18, 2006Assignee: Nippon Shokubai Co., Ltd.Inventors: Hisashi Semba, Yukio Dobashi
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Patent number: 7078226Abstract: A process for preparing optically active amines, a process for preparing racemic amines which can be resolved using optically active carboxylic acids or enzymes, and racemic and optically active amines and optically active amides are described.Type: GrantFiled: November 13, 2000Date of Patent: July 18, 2006Assignee: BASF AktiengesellschaftInventors: Klaus Ditrich, Wolfgang Siegel
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Patent number: 7067305Abstract: A process for the resolution of an enantiomeric mixture of ?-lactams containing an ester, the process comprising selectively hydrolyzing the ester of one of the enantiomers by combining the mixture with homogenized liver.Type: GrantFiled: April 11, 2003Date of Patent: June 27, 2006Assignee: FSU Research Foundation, Inc.Inventors: Robert A. Holton, Phong Vu
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Patent number: 7067291Abstract: Methods for preparing enantiomerically enriched aminopentanenitriles are provided. The methods involve selective acylation of an enantiomeric mixture of 3-aminopentanenitrile or selective hydrolysis of an enantiomeric mixture of 3-aminopentanenitrile amide in the presence of an enzyme selected from the group comprising lipase, esterase, and acylase. The methods yield R-aminopentanenitrile, which can be used to produce pharmaceutical products.Type: GrantFiled: December 20, 2002Date of Patent: June 27, 2006Assignee: Pfizer Inc.Inventors: David R. Allen, Vadim V. Mozhaev, Rao H. Valivety
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Patent number: 7063977Abstract: A method for the resolution of a mixture of the cis or trans enantiomers of a compound of the formula wherein R1 is —O—C(O)alkyl, —O—C(O)aryl or —O—C(O)cycloalkyl by contacting the mixture with a carboxylic ester hydrolase enzyme which catalyzes the stereoselective hydrolysis of the mixture and the use of such enantiomers to produce antitumor compounds which are especially suitable for oral administration.Type: GrantFiled: August 20, 2002Date of Patent: June 20, 2006Assignee: Bristol-Myers Squibb CompanyInventor: Ramesh N. Patel
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Patent number: 7053225Abstract: Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-[(dimethylmethylene)dioxy]-5-hydroxy-tricyclo[5.2.1.02,6]dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo[5.2.1.02,6]deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.Type: GrantFiled: February 21, 2003Date of Patent: May 30, 2006Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Kunio Ogasawara
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Patent number: 7053224Abstract: Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-[(dimethylmethylene)dioxy]-5-hydroxy-tricyclo[5.2.1.02,6dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo[5.2.1.02,6]deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.Type: GrantFiled: February 21, 2003Date of Patent: May 30, 2006Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Kunio Ogasawara
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Patent number: 7045341Abstract: A chemoenzymatic process for the stereoselective preparation of both the (R) and (S) enantiomers of 3-hydroxy-3-(2-thienyl) propanenitrile has been developed. These optically pure key intermediates were prepared by enzymatic resolution of (±)3-hydroxy-3-(2-thienyl) propanenitrile both by transesterification and by hydrolysis reaction which were then transformed to both enantiomers of duloxetine.Type: GrantFiled: March 20, 2003Date of Patent: May 16, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Ahmed Kamal, Bhasker Ramesh Khanna Gollapalli, Ramu Rondla, Venkateswara Rao Maddamsetty
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Patent number: 7026144Abstract: A process of separating a single desired stereoisomer from a racemic mixture of eight stereoisomers of a compound of formula (III), wherein R1 represents an isopropanol group, an isopropyl group or an isopropylene group, includes the steps of: contacting the racemic mixture in a suitable organic solvent with an esterifying agent and a stereospecific enzyme which stereoselectively esterifies the —OH group of the desired stereoisomer, for a time sufficient to convert a desired percentage of the desired stereoisomer to a compound of formula (IV), wherein R1 is as defined above and R4 is an alkyl or an aryl group, to give a first reaction product including the compound of formula (IV), the organic solvent, the unconverted stereoisomers of the compound of formula (III), excess esterifying agent and by-products of the reaction; and separating the compound of formula (IV) from the first reaction product.Type: GrantFiled: June 11, 2001Date of Patent: April 11, 2006Assignee: CSIRInventors: Jennifer Ann Chaplin, Neil Stockenstrom Gardiner, Robin Kumar Mitra, Christopher John Parkinson, Madrie Portwig, Butana Andrew Mboniswa, Melanie Daryl Evans-Dickson, Dean Brady, Stephanus Francois Marais, Shavani Reddy
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Patent number: 7015029Abstract: There is provided a novel method for producing an optically active (4R)-1,3-thiazolidine-4-carboxylic acid by allowing cells of a microorganism or a preparation obtained from cells of a microorganism having activity for stereoselectively hydrolyzing an optically active (4R)-1,3-thiazolidine-4-carboxylic acid amide to act on a mixture of (4R)- and (4S)-enantiomers of a 1,3-thiazolidine-4-carboxylic acid amide to produce the optically active (4R)-1,3-thiazolidine-4-carboxylic acid and separating the optically active (4R)-1,3-thiazolidine-4-carboxylic acid.Type: GrantFiled: December 11, 2001Date of Patent: March 21, 2006Assignee: Mitsubishi Gas Chemical Co, Inc.Inventors: Yutaka Tamura, Takahiro Kato, Go Nakamura, Toshio Kondo
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Patent number: 7011963Abstract: The invention relates to a process for synthesis, by inverse bead polymerization of a monomer phase, of a bead-like, cross-linked, hydrophilic copolymer which has binding activity toward ligands containing nucleophilic groups. The invention relates to support polymer materials with high binding capacity for penicillin acylase and low swelling factor, as well as to use of the same.Type: GrantFiled: February 1, 1999Date of Patent: March 14, 2006Assignee: Roehm GmbH & Co KGInventors: Christian Meier, Thomas Suefke, Hans-Ulrich Petereit, Roger Recktenwald, Thomas Boller
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Patent number: 7005282Abstract: Disclosed is an ionic liquid-coated enzyme, wherein the ionic liquid is an organic salt which presents as a liquid phase at a temperature of about 150° C. or below. The ionic liquid-coated enzyme according to the present invention remarkably improves enzyme functions, such as enantioselectivity and stability, when the enzyme which may be lipase is coated with an ionic liquid. Further, even in the case of when the ionic liquid-coated enzyme is reused, the enantiomeric excess, enantioselectivity, and activity are not degenerated. The coated enzyme is usable as a catalyst for providing a chiral intermediate required in the synthesis of chiral pesticides, medicines, natural chemicals, and so on.Type: GrantFiled: January 13, 2003Date of Patent: February 28, 2006Assignee: POSCO and POSTECH FoundationInventors: Mahn-Joo Kim, Jae Kwan Lee
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Patent number: 6987010Abstract: The present invention relates to processes for the preparation of enantiomerically enriched ?-amino acids. The invention also relates to advantageous esters of ?-amino acids of the general formula (I) and to the use thereof in the enzymatic preparation of enantiomerically enriched ?-amino acids.Type: GrantFiled: February 8, 2005Date of Patent: January 17, 2006Assignee: Degussa AGInventors: Harald Gröger, Helge Werner
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Patent number: 6979561Abstract: The present invention relates to a process for the biocatalyst-mediated enantioselective conversion of enantiomeric mixtures of hydrophobic esters uing a biphasic solvent system. More particularly, the present invention relates to the enzyme-mediated enantioselective synthesis of anti-viral compounds, such as 2-hydroxymethyl-5-(5-flurocytosin-1-yl)-1,3-oxathiolane (FTC) and its analogues, in a non-homogenous reaction system.Type: GrantFiled: June 1, 2000Date of Patent: December 27, 2005Assignee: Gilead Sciences, Inc.Inventors: Merrick R. Almond, Yao Yiming, Wang Yi Fong
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Patent number: 6958233Abstract: The present invention relates to a process for the preparation of pharmaceutically acceptable salts of (R,S)-S-adenosyl-L-methionine and allows to obtain the salified (R)-(+)-S-adenosyl-L-methionine diasteroisomer in amounts lower than or equal to 3% with respect to the salified (S)-(+)-S-adenosyl-L-methionine diastereoisomer; the salts that can be obtained by the process of the invention keep their configuration stable in time.Type: GrantFiled: May 13, 2002Date of Patent: October 25, 2005Assignee: Chementecno S.r.l.Inventors: Marco Berna, Lino Sivieri, Gianni Santambrogio, Ermanno Valoti
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Patent number: 6953678Abstract: A process for the resolution of enantiomeric mixtures of a chiral carboxylic acid, including an esterification reaction of the carboxylic acid in an organic solvent, in the presence of a stereoselective hydrolase, characterized in that an orthoester of the formula R1—C(OR2)3, in which R1 is selected from H and C1–C4alkyl and R2 is C1–C8alkyl or —CH2—C6-10aryl, is used as the esterification reactive.Type: GrantFiled: July 25, 2000Date of Patent: October 11, 2005Assignee: Consiglio Nazionale Delle RicercheInventors: Raffaele Morrone, Giovanni Nicolosi, Mario Piattelli
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Patent number: 6939693Abstract: An enzymatic synthesis and composition of oligomers and co-oligomers comprised of ?-hydroxy carboxylic acids and ?-amino acids or peptides is disclosed. In a preferred embodiment, a ?-hydroxy carboxylic acid with a specific chiral configuration is linked by an amide linkage to a ?-amino acid specific with a specific chiral configuration or linked by an amide linkage to a peptide made up of ?-amino acid monomers having identical chiral configurations. Proteolytic enzymes catalyze oligomerization of the ?-hydroxy carboxylic acid and ?-amino acid. The degree and distribution of oligomerization varies upon the type and concentrations of different reaction mixtures utilized and upon the length of allowed reaction time. The resultant oligomers may be provided to animals such as ruminants as bioavailable amino acid supplements that are resistant to degradation in the rumen and other animals such as swine, poultry and aquatic animals.Type: GrantFiled: May 2, 2002Date of Patent: September 6, 2005Assignee: Novus International, Inc.Inventors: Stephen J. Lorbert, Charles S. Schasteen, Paul K. S. Nam, Daniel Forciniti, Mathur P. Rajesh, Shubhender Kapila
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Patent number: 6908752Abstract: The present invention relates to a process for the preparation of the enantiomeric forms of 2-substituted 2-(2,5-dioxoimidazolidin-1-yl)acetic acid derivatives of the formula I, wherein R1, R2 and R3 have the meanings given in the claims, by stereodifferentiating conversion of mixtures of the enantiomers with the aid of enzymes.Type: GrantFiled: July 12, 2002Date of Patent: June 21, 2005Assignee: Aventis Pharma Deutschland GmbHInventor: Wolfgang Holla
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Patent number: 6902927Abstract: An enzymatic process permitting the enantiomeric resolution of amino acids is provided. More specifically, this process for separating the enantiomers of an amino acid comprises treating a racemic mixture of the amino acid with glutaric anhydride and then with the enzyme glutaryl-7-ACA acylase so as to recover one of the enantiomers of the amino acid, the other enantiomer remaining in the form of the corresponding glutarylamide derivative.Type: GrantFiled: September 3, 2002Date of Patent: June 7, 2005Assignee: Aventis Pharma S.A.Inventors: Christophe Salagnad, Claude Gobert, Marie-Odile Dury
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Patent number: 6900037Abstract: The present invention provides a method for producing amide compounds using hydroxyl nitrile compounds and microorganisms and/or enzymatically active material having cyanide-resistant nitrile hydratase activity, e.g., Rhodococcus equi XL-l. Furthermore, the amide compounds can be produced while the enzymatic activity of this microorganism can be stably maintained during the reaction.Type: GrantFiled: June 13, 2002Date of Patent: May 31, 2005Assignee: Daicel Chemical Industries, Ltd.Inventors: Tohru Nagasawa, Akinobu Matsuyama
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Patent number: 6897058Abstract: Method for the preparation of an enantiomerically enriched acylated amine wherein a phenylacetic acid derivative is brought into contact with a mixture of enantiomers of an amine H2NCR1R2R3, in which R1, R2, R3 are not equal to each other and each independently stand for H, CN, a whether or not substituted (cyclo)alkyl, ary-, alkylaryl or arylalkyl group, whether or not cyclic heteroalkyl or heteroaryl group with one or more N, O or S atoms or in which R1 and R2 (and R3) together with the C-atom to which they have been bound form a (bi)cyclic group that optionally contains one or more N, O of S atoms, in the presence of a Pen-G acylase derived from Alcaligenes faecalis. And method for the preparation of enantiomerically enriched amine of formula H2NCR1R2R3, in which R1, R2, R3 are as defined above, wherein an acylated amine is brought into contact with a Pen-G acylase originating from Alcaligenes faecalis.Type: GrantFiled: August 30, 2001Date of Patent: May 24, 2005Assignee: DSM IP Assets B.V.Inventors: Vytautas-Juozapas Kajetono {hacek over (S)}vedas, Dorel Teodor Guranda, Roger Arthur Sheldon, Frederik Rantwijk Van, Lukas Michaël Langen Van
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Patent number: 6893861Abstract: The invention relates to a biotechnological method for producing trifluoro-3(R)-hydroxybutyric acid derivatives of the general formula (I), where R1 represents —OR2, where R2 is hydrogen, C1-10 alkyl, C1-10 alkenyl, C3-8 cy-cloalkyl, aryl, alkoxyalkyl or alkoxyalkoxyalkyl; —NR3R4, where R3 and R4 are the same or different and represent hydrogen, C1-10 alkyl, C1-10 alkenyl, C3-8 cycloalkyl or aryl; or —SR5, where R5 represents hydrogen, C1-10 alkyl, C1-10 alkenyl, aryl or C3-8 cycloalkyl, based on a trifluoroacetoacetic acid derivative of the general formula (II), where R1 has the meaning given above, by means of micro-organisms which are able to reduce a carbonyl function or by means of a cell-free enzyme extract of said micro-organisms.Type: GrantFiled: February 18, 1999Date of Patent: May 17, 2005Assignee: Lonza AGInventors: Michael Petersen, Olwen Birch, Sakayu Shimizu, Andreas Kjener, Marie-Luise Hischier, Susanne Thöni
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Patent number: 6887700Abstract: A process is provided for preparing an enantiopure 1,3-dioxolan-4-one or 1,3-oxathiolan-5-one derivative, which includes bringing a mixture containing enantiomeric 1,3-dioxolan-4-one or 1,3-oxathiolan-5-one derivatives and an enzyme with hydrolytic activity into contact in the presence of a nucleophile. Cleaving a dioxolanone/oxathiolanone ring of one enantiomer occurs by the enzyme with hydrolytic activity and, after the cleavage of one enantiomer has taken place, the uncleaved enantiomer of the 1,3-dioxolan-4-one or 1,3-oxathiolan-5-one derivative is isolated.Type: GrantFiled: January 30, 2002Date of Patent: May 3, 2005Assignee: Consortium für Elektrochemische Industrie GmbHInventors: Alfred Popp, Jürgen Stohrer, Hermann Petersen, Andrea Gilch, Jodoca Rockinger-Mechlem
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Patent number: 6869781Abstract: The present invention relates to processes for the preparation of enantiomerically enriched ?-amino acids. The invention also relates to advantageous esters of ?-amino acids of the general formula (I) and to the use thereof in the enzymatic preparation of enantiomerically enriched ?-amino acids.Type: GrantFiled: May 7, 2003Date of Patent: March 22, 2005Assignee: Degussa AGInventors: Harald Gröger, Helge Werner