WO2003010312A3 - Nucleic acid sequences encoding enantioselective amidases - Google Patents

Nucleic acid sequences encoding enantioselective amidases Download PDF

Info

Publication number
WO2003010312A3
WO2003010312A3 PCT/NL2002/000471 NL0200471W WO03010312A3 WO 2003010312 A3 WO2003010312 A3 WO 2003010312A3 NL 0200471 W NL0200471 W NL 0200471W WO 03010312 A3 WO03010312 A3 WO 03010312A3
Authority
WO
WIPO (PCT)
Prior art keywords
carboxylic acid
nucleic acid
fermentation
enantiomerically enriched
relates
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/NL2002/000471
Other languages
French (fr)
Other versions
WO2003010312A2 (en
Inventor
Theodorus Sonke
Renate Francisca Tandler
Cornelis Gerrit Nijs Korevaar
Van Friso Bernard Jan Assema
Van Der Rudolf Pol
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Priority to JP2003515662A priority Critical patent/JP2004536608A/en
Priority to DK02747739T priority patent/DK1409688T3/en
Priority to CA002454701A priority patent/CA2454701A1/en
Priority to US10/484,681 priority patent/US7241602B2/en
Priority to DE60220797T priority patent/DE60220797T2/en
Priority to AU2002318056A priority patent/AU2002318056A1/en
Priority to EP02747739A priority patent/EP1409688B1/en
Publication of WO2003010312A2 publication Critical patent/WO2003010312A2/en
Publication of WO2003010312A3 publication Critical patent/WO2003010312A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/38—Chemical stimulation of growth or activity by addition of chemical compounds which are not essential growth factors; Stimulation of growth by removal of a chemical compound
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
    • C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Molecular Biology (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

Abstract

The invention relates to a nucleic acid sequence encoding an enantioselective amidase with an amino acid sequence, which amino acid sequence has at least 70% identity with SEQ ID NO: 2. The invention also relates to a process for the fermentation, comprising a batch and a feed phase, of a microorganism in a fermentation medium, wherein the microorganism expresses a nucleic acid according to the invention and wherein between 0.5 and 50mg/l_fermentation medium Zn2+ is fed during the fermentation. The invention also relates to a process for the preparation of an enantiomerically enriched carboxylic acid and/or an enantiomerically enriched carboxylic acid amide, in which a mixture of the corresponding D- and L-carboxylic acid amides is contacted with an expression product according to the invention in the presence of between 0.01mM and 100mM Zn2+, whereby one of the enantiomers of the carboxylic acid amide is enantioselectively hydrolysed to form the corresponding enantiomerically enriched carboxylic acid, while the other enantiomer of the carboxylic acid amide remains unchanged.
PCT/NL2002/000471 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases Ceased WO2003010312A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2003515662A JP2004536608A (en) 2001-07-23 2002-07-15 Nucleic acid sequence encoding an enantioselective amidase
DK02747739T DK1409688T3 (en) 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases
CA002454701A CA2454701A1 (en) 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases
US10/484,681 US7241602B2 (en) 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases
DE60220797T DE60220797T2 (en) 2001-07-23 2002-07-15 NUCLEIC ACID SEQUENCES CODING FOR ENANTIOSELECTIVE AMIDASES
AU2002318056A AU2002318056A1 (en) 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases
EP02747739A EP1409688B1 (en) 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP01202822 2001-07-23
EP01202821.3 2001-07-23
EP01202822.1 2001-07-23
EP01202821 2001-07-23

Publications (2)

Publication Number Publication Date
WO2003010312A2 WO2003010312A2 (en) 2003-02-06
WO2003010312A3 true WO2003010312A3 (en) 2003-10-30

Family

ID=26076964

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2002/000471 Ceased WO2003010312A2 (en) 2001-07-23 2002-07-15 Nucleic acid sequences encoding enantioselective amidases

Country Status (11)

Country Link
US (1) US7241602B2 (en)
EP (1) EP1409688B1 (en)
JP (1) JP2004536608A (en)
CN (1) CN1555416A (en)
AT (1) ATE365216T1 (en)
AU (1) AU2002318056A1 (en)
CA (1) CA2454701A1 (en)
DE (1) DE60220797T2 (en)
DK (1) DK1409688T3 (en)
ES (1) ES2286262T3 (en)
WO (1) WO2003010312A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5190207B2 (en) * 2007-03-01 2013-04-24 三菱レイヨン株式会社 Preservative, activation activator and deactivation preventive for amidase containing zinc or salt thereof
JP5138271B2 (en) * 2007-05-16 2013-02-06 三菱レイヨン株式会社 Highly active amidase enzyme solution and preparation method thereof
EP2123767A1 (en) 2008-05-20 2009-11-25 DSM IP Assets B.V. Preparation of epsilon-caprolactam via lysine cyclisation
EP2123768A1 (en) 2008-05-20 2009-11-25 DSM IP Assets B.V. Preparation of (Z)-6,7-dihydro-1H-azepin-2(5H)-one
TW201002823A (en) * 2008-05-20 2010-01-16 Dsm Ip Assets Bv Preparation of alpha-amino-epsilon-caprolactam via lysine cyclisation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0494716A2 (en) * 1991-01-11 1992-07-15 Dsm N.V. Enzyme-catalysed preparation of optically active carboxylic acids
WO2000063354A1 (en) * 1999-04-16 2000-10-26 Mitsubishi Rayon Co., Ltd. Novel amidase gene

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU74142A1 (en) * 1976-01-08 1977-07-22
PT1144656E (en) 1998-05-25 2004-07-30 Qiagen Gmbh PROCESS FOR THE ISOLATION OF CCC PLASMIDE DNA
AU4436900A (en) 1999-04-29 2000-11-17 Dsm N.V. Expression cassette for efficient production of a protein

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0494716A2 (en) * 1991-01-11 1992-07-15 Dsm N.V. Enzyme-catalysed preparation of optically active carboxylic acids
WO2000063354A1 (en) * 1999-04-16 2000-10-26 Mitsubishi Rayon Co., Ltd. Novel amidase gene
EP1174499A1 (en) * 1999-04-16 2002-01-23 Mitsubishi Rayon Co., Ltd. Novel amidase gene

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
KAPTEIN B ET AL: "Enantiopure C-alpha-tetrasubstituted alpha-amino acids. Chemo-enzymatic synthesis and application to turn-forming peptides", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 30, 23 July 2001 (2001-07-23), pages 6567 - 6577, XP004275079, ISSN: 0040-4020 *
KOMEDA HIDENOBU ET AL: "Gene cloning, nucleotide sequencing, and purification and characterization of the D-stereospecific amino-acid amidase from Ochrobactrum anthropi SV3.", EUROPEAN JOURNAL OF BIOCHEMISTRY, vol. 267, no. 7, April 2000 (2000-04-01), pages 2028 - 2035, XP002243586, ISSN: 0014-2956 *
MAYAUX J-F ET AL: "PURIFICATION, CLONING, AND PRIMARY STRUCTURE OF AN ENANTIOMER-SELECTIVE AMIDASE FROM BREVIBACTERIUM SP. STRAIN R312: STRUCTURAL EVIDENCE FOR GENETIC COUPLING WITH NITRILE HYDRATASE", JOURNAL OF BACTERIOLOGY, WASHINGTON, DC, US, vol. 172, no. 12, 1 December 1990 (1990-12-01), pages 6764 - 6773, XP000283074, ISSN: 0021-9193 *
TWEEL VAN DEN W J J ET AL: "OCHROBACTRUM ANTHROPI NCIMB 40321: A NEW BIOCATALYST WITH BROAD-SPECTRUM L-SPECIFIC AMIDASE ACTIVITY", APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, SPRINGER VERLAG, BERLIN, DE, vol. 39, no. 3, 1993, pages 296 - 300, XP008006772, ISSN: 0175-7598 *

Also Published As

Publication number Publication date
ES2286262T3 (en) 2007-12-01
US7241602B2 (en) 2007-07-10
DE60220797T2 (en) 2008-04-10
DE60220797D1 (en) 2007-08-02
EP1409688B1 (en) 2007-06-20
ATE365216T1 (en) 2007-07-15
US20050079595A1 (en) 2005-04-14
JP2004536608A (en) 2004-12-09
EP1409688A2 (en) 2004-04-21
AU2002318056A1 (en) 2003-02-17
WO2003010312A2 (en) 2003-02-06
DK1409688T3 (en) 2007-09-17
CA2454701A1 (en) 2003-02-06
CN1555416A (en) 2004-12-15

Similar Documents

Publication Publication Date Title
Martinkova et al. Nitrile-and amide-converting microbial enzymes: stereo-, regio-and chemoselectivity
Sugai et al. Biocatalysis in organic synthesis: the use of nitrile-and amide-hydrolyzing microorganisms
HU9904447D0 (en) Process for fermentative production of d-pantotenic acid by increase pand-gene effect
IL142397A0 (en) Method for producing chiral carboxylic acids from nitriles with the assistance of a nitrilase or microorganisms which contain a gene for the nitrilase
EP1043398A1 (en) Expression vector pUC NT, DNA coding for decarbamylase improved in thermostability and use thereof
MY127700A (en) (alpha) -ketoglutarate dehydrogenase gene
EP1513946B1 (en) Polypeptides having alpha-h-alpha amino acid amide racemase activity and nucleic acids encoding the same
WO1997012964A3 (en) Nucleic acid fragments encoding stereospecific nitrile hydratase and amidase enzymes and recombinant microorganisms expressing those enzymes useful for the production of chiral amides and acides
DE60043424D1 (en) RHODOCOCCUS STRAIN, NITRILASE GENES FROM RHODOCOCCUS, NITRILHYDRATAS GENE AND AMIDASE GENE AND METHOD FOR THE PRODUCTION OF CARBOXYLIC ACIDS UNDER USE
EP0943687A3 (en) Method of producing L-serine by fermentation
US5869298A (en) Stable mutants of D-N-α-carbamoylase and process for preparing D-α-amino acids
EP0332379B1 (en) Production process of L-alpha-amino acids
US20030109013A1 (en) DNA encoding hydantoinase, DNA encoding N-carbamyl-L-amino acid hydrolase, recombinant DNA, transformed cell, method of producing protein, and method of producing optically active amino acid
AU2002318056A1 (en) Nucleic acid sequences encoding enantioselective amidases
Tokuyama Discovery and application of a new enzyme N-acylamino acid racemase
HUP0201850A3 (en) Method for the production of l-amino acids from their racemic n-acetyl-d,l-derivatives by enzymatic racemate cleavage by means of isolated recombinant enzymes
EP0651821B1 (en) Enzymatic resolution of a racemic mixture of stereospecific gaba-t inhibitors
EP0780473A2 (en) Thermostable mutants of D-N-alpha-Carbamoylase
US5834258A (en) Process for the preparation of D-α-amino acids
CA2264651A1 (en) Microorganism, lactamase enzyme obtained therefrom, and their use
MY127965A (en) Enzymatic process for the enantiomeric resolution of amino acids
WO2004058701A3 (en) Biocatalytic preparation of enantiomerically enriched aminopentanenitrile
EP2130925A1 (en) Method for production of optically active amino acid
Wahl et al. Microbial production, purification, and characterization of (S)-specific N-acetyl-2-amino-1-phenyl-4-pentene amidohydrolase from Rhodococcus globerulus K1/1
MXPA04001535A (en) Enzymatic method for the enantiomeric resolution of amino acids.

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG US UZ VN YU ZA ZM

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2454701

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 128/CHENP/2004

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2003515662

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 2002747739

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 20028181360

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 2002747739

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWE Wipo information: entry into national phase

Ref document number: 10484681

Country of ref document: US

WWG Wipo information: grant in national office

Ref document number: 2002747739

Country of ref document: EP