WO2002061107A3 - Process for the preparation of enantiomer-enriched amino acids - Google Patents

Process for the preparation of enantiomer-enriched amino acids Download PDF

Info

Publication number
WO2002061107A3
WO2002061107A3 PCT/NL2002/000072 NL0200072W WO02061107A3 WO 2002061107 A3 WO2002061107 A3 WO 2002061107A3 NL 0200072 W NL0200072 W NL 0200072W WO 02061107 A3 WO02061107 A3 WO 02061107A3
Authority
WO
WIPO (PCT)
Prior art keywords
phosphate ion
enantiomer
metal salt
amino acid
preparation
Prior art date
Application number
PCT/NL2002/000072
Other languages
French (fr)
Other versions
WO2002061107A2 (en
Inventor
Wilhelmus Hubertus Jos Boesten
Joannes Gerardus Theo Kierkels
Original Assignee
Dsm Ip Assets Bv
Boesten Wilhelmus H J
Joannes Gerardus Theo Kierkels
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, Boesten Wilhelmus H J, Joannes Gerardus Theo Kierkels filed Critical Dsm Ip Assets Bv
Priority to EP02711530A priority Critical patent/EP1404854A2/en
Priority to HU0302864A priority patent/HUP0302864A2/en
Priority to AU2002230274A priority patent/AU2002230274A1/en
Priority to KR10-2003-7009948A priority patent/KR20030071868A/en
Priority to JP2002561661A priority patent/JP2004521623A/en
Publication of WO2002061107A2 publication Critical patent/WO2002061107A2/en
Publication of WO2002061107A3 publication Critical patent/WO2002061107A3/en

Links

Classifications

    • 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
    • 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
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Process for the preparation of a chiral amino acid enriched in the D-enantiomer, in which a mixture of the enantiomers of the corresponding N-carbamoylamino acid is brought into contact with a D-carbamoylase with ammonia being liberated, the ammonia being removed with the aid of a bivalent metal salt of a phospahte, a monohydrogen phosphate or a dihydrogen phosphate ion. In one embodiment the enzymatic decarbamoylation is carried out in the presence of a bivalent metal salt of a phosphate ion, a monohydrogen phosphate ion or a dihydrogen phosphate ion. In another embodiment the reaction mixture is brought into contact via an external loop, after separation of the solid present, with the bivalent metal salt of a phosphate ion, monohydrogen phosphate ion or dihydrogen phosphate ion. The chiral amino acid enriched in the D-enantiomer can also be obtained by enzymatically converting the corresponding hydantoin with the aid of a hydantoinase into the corresponding N-carbamoylamino acid, which is subsequently converted according to the invention into the amino acid enriched in the D-enantiomer.
PCT/NL2002/000072 2001-01-31 2002-01-31 Process for the preparation of enantiomer-enriched amino acids WO2002061107A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP02711530A EP1404854A2 (en) 2001-01-31 2002-01-31 Process for the preparation of enantiomer-enriched amino acids
HU0302864A HUP0302864A2 (en) 2001-01-31 2002-01-31 Process for the preparation of enantiomer-enriched amino acids
AU2002230274A AU2002230274A1 (en) 2001-01-31 2002-01-31 Process for the preparation of enantiomer-enriched amino acids
KR10-2003-7009948A KR20030071868A (en) 2001-01-31 2002-01-31 Process for the preparation of enantiomer-enriched amino acids
JP2002561661A JP2004521623A (en) 2001-01-31 2002-01-31 Method for producing enantiomer-rich amino acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1017250 2001-01-31
NL1017250A NL1017250C1 (en) 2001-01-31 2001-01-31 Process for the preparation of enantiomerically enriched amino acids.

Publications (2)

Publication Number Publication Date
WO2002061107A2 WO2002061107A2 (en) 2002-08-08
WO2002061107A3 true WO2002061107A3 (en) 2003-12-31

Family

ID=19772826

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2002/000072 WO2002061107A2 (en) 2001-01-31 2002-01-31 Process for the preparation of enantiomer-enriched amino acids

Country Status (9)

Country Link
EP (1) EP1404854A2 (en)
JP (1) JP2004521623A (en)
KR (1) KR20030071868A (en)
CN (1) CN1520460A (en)
AU (1) AU2002230274A1 (en)
CZ (1) CZ20032077A3 (en)
HU (1) HUP0302864A2 (en)
NL (1) NL1017250C1 (en)
WO (1) WO2002061107A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1019416C2 (en) * 2001-11-23 2003-06-02 Dsm Nv Process for preparing an enantiomerically enriched α-amino acid.
KR100600698B1 (en) * 2004-08-26 2006-07-14 삼성전자주식회사 Image reproduction apparatus and remote controller for control image reproduction apparatus and method for converting channel thereof
EP2508615A4 (en) 2009-12-04 2013-07-10 Mitsubishi Gas Chemical Co Process for production of optically active amino acid or optically active amino acid amide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984000885A1 (en) * 1982-09-09 1984-03-15 Organon Teknika Corp Ammonia scavenger
DE3732896A1 (en) * 1986-11-07 1988-08-25 Schulze Rettmer Rainer Process for eliminating ammonia and phosphate from waste water and process water
EP0490396A1 (en) * 1990-12-14 1992-06-17 DEUTSCHE NALCO-CHEMIE GmbH Process for recovery of ammonia from process and waste waters

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984000885A1 (en) * 1982-09-09 1984-03-15 Organon Teknika Corp Ammonia scavenger
DE3732896A1 (en) * 1986-11-07 1988-08-25 Schulze Rettmer Rainer Process for eliminating ammonia and phosphate from waste water and process water
EP0490396A1 (en) * 1990-12-14 1992-06-17 DEUTSCHE NALCO-CHEMIE GmbH Process for recovery of ammonia from process and waste waters

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHAO Y-P ET AL.: "One-step production of D-p-hydroxyphenylglycine by recombinant Escherichia coli strains", BIOTECHNOLOGY PROGRESS, vol. 15, no. 6, November 1999 (1999-11-01), pages 1039 - 1045, XP000952050 *
CHAO Y-P ET AL.: "Production of D-p-hydroxyphenylglycine by N-carbamoyl-D-amino acid amidohydrolase-overproducing Escherichia coli strains", BIOTECHNOLOGY PROGRESS, vol. 15, no. 4, July 1999 (1999-07-01), pages 603 - 607, XP000951585 *
KIM G-J ET AL.: "Optimization of the enzymatic synthesis of D-p-hydroxyphenylglycine from DL-5-substituted hydantoin using D-hydantoinase and N- carbamoylase", ENZYME MICROB. TECHNOL., vol. 17, no. 1, 1995, pages 63 - 67, XP000951523 *
RUNSER S ET AL.: "D-p-hydroxyphenylglycine production from DL-5-p- hydroxyphenylhydantoin by Agrobacterium sp.", APPL. MICROBIOL. BIOTECHNOL., vol. 33, no. 4, 1990, pages 382 - 388, XP000951524 *
WEAST R C (EDITOR): "CRC Handbook of Chemistry and Physics", 1982, CRC PRESS INC., BOCA RATON, FLORIDA, XP002239470 *

Also Published As

Publication number Publication date
WO2002061107A2 (en) 2002-08-08
EP1404854A2 (en) 2004-04-07
CN1520460A (en) 2004-08-11
JP2004521623A (en) 2004-07-22
AU2002230274A1 (en) 2002-08-12
KR20030071868A (en) 2003-09-06
NL1017250C1 (en) 2002-08-01
CZ20032077A3 (en) 2003-11-12
HUP0302864A2 (en) 2003-12-29

Similar Documents

Publication Publication Date Title
EP2064331B1 (en) Process for preparation of optically active N-protected 3-aminopyrrolidine or N-protected 3-aminopiperidine by optical resolution of racemic amine mixtures employing an omega-transaminase
Olivieri et al. Enzymatic conversion of N carbamoyl-D-amino acids to D-amino acids
WO2003059865A1 (en) Processes for the preparation of glutamic acid compounds and intermediates thereof and novel intermediates used in the processes
EP1818411A1 (en) Process for the preparation of optically active chiral amines
EP2894227A3 (en) Process for preparing dipeptidyl peptidase iv inhibitors and intermediates therefor
WO2002036742A3 (en) Method for chemical transformation using a mutated enzyme
HUP0201152A2 (en) Process for the production of non-proteinogenic amino acids
WO2002033110A3 (en) PRODUCTION OF α-HYDROXY-CARBOXYLIC ACIDS USING A COUPLED ENZYME SYSTEM
WO2002061107A3 (en) Process for the preparation of enantiomer-enriched amino acids
MY140308A (en) Method for the production of high-molecular polyamides
DK0904348T3 (en) Process for the preparation of amino alcohols and derivatives thereof
NO984447L (en) Process for the preparation of optically active 2-amino-w-oxoalkanoic acid derivatives
WO2003068909A3 (en) Transaminases, nucleic acids encoding them and methods of making and using them
WO2002085840A9 (en) Process for producing n-formylamino acid and utilization thereof
MY127965A (en) Enzymatic process for the enantiomeric resolution of amino acids
HK1219507A1 (en) Method for producing optically active phenylalanine compounds from cinnamic acid derivatives employing a phenylalanine ammonia lyase derived from idiomarina loihiensis idiomarina loihiensis
US5707837A (en) Method of producing (R)-tertiary leucine
JP2618619B2 (en) Method for producing D-glutamic acid
WO2003044206A3 (en) Process for the preparation of an enantiomerically enriched a-amino acid
WO2004111227A3 (en) Screening process for hydantoin racemases
WO2002095045A3 (en) Method of preparing aliphatic carboxylic acids by enzymatic hydrolysis of aliphatic nitrile compounds
DK0542098T3 (en) Process for Chemical Racemization of 5-Mono-Substituted Hydantoins
JPH05211891A (en) Method for producing optically active vinyl glycine in form liberated or protected by enzymatic subject selecting hydrolysis

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

AL Designated countries for regional patents

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 CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE 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: 2002711530

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 1020037009948

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 2002561661

Country of ref document: JP

Ref document number: 1174/CHENP/2003

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: PV2003-2077

Country of ref document: CZ

WWE Wipo information: entry into national phase

Ref document number: 028044282

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 1020037009948

Country of ref document: KR

WWP Wipo information: published in national office

Ref document number: PV2003-2077

Country of ref document: CZ

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: 2002711530

Country of ref document: EP

WWR Wipo information: refused in national office

Ref document number: PV2003-2077

Country of ref document: CZ

WWW Wipo information: withdrawn in national office

Ref document number: 2002711530

Country of ref document: EP