NL8800224A - Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren. - Google Patents

Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren. Download PDF

Info

Publication number: NL8800224A
Authority: NL; Netherlands
Prior art keywords: alpha; amino acid; sulfur; process according; preparation
Prior art date: 1988-01-29

Application number

NL8800224A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1988-01-29

Filing date

1988-01-29

Publication date

1989-08-16

1988-01-29 Application filed by Stamicarbon filed Critical Stamicarbon

1988-01-29 Priority to NL8800224A priority Critical patent/NL8800224A/nl

1989-01-26 Priority to EP89200154A priority patent/EP0327156A1/de

1989-08-16 Publication of NL8800224A publication Critical patent/NL8800224A/nl

Links

150000007649 L alpha amino acids Chemical class 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 3
238000002360 preparation method Methods 0.000 claims description 28
102000004190 Enzymes Human genes 0.000 claims description 27
108090000790 Enzymes Proteins 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 24
239000011593 sulfur Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 23
-1 hydroxylamine compound Chemical class 0.000 claims description 20
241000589776 Pseudomonas putida Species 0.000 claims description 16
244000005700 microbiome Species 0.000 claims description 11
102000004400 Aminopeptidases Human genes 0.000 claims description 9
108090000915 Aminopeptidases Proteins 0.000 claims description 9
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
238000006911 enzymatic reaction Methods 0.000 claims description 7
241001598040 Pseudomonas reptilivorous Species 0.000 claims description 6
239000012736 aqueous medium Substances 0.000 claims description 3
229940088598 enzyme Drugs 0.000 description 25
230000000694 effects Effects 0.000 description 12
235000008206 alpha-amino acids Nutrition 0.000 description 9
235000001014 amino acid Nutrition 0.000 description 9
150000001413 amino acids Chemical class 0.000 description 9
150000001370 alpha-amino acid derivatives Chemical class 0.000 description 6
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
235000006109 methionine Nutrition 0.000 description 5
229930182817 methionine Natural products 0.000 description 5
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
230000006340 racemization Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
150000007650 D alpha amino acids Chemical class 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
102000004879 Racemases and epimerases Human genes 0.000 description 3
108090001066 Racemases and epimerases Proteins 0.000 description 3
150000001371 alpha-amino acids Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
UNQHGXLQKSZYQU-UHFFFAOYSA-N 2-(thiophen-2-ylamino)acetic acid Chemical compound OC(=O)CNC1=CC=CS1 UNQHGXLQKSZYQU-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 2
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
SFSJZXMDTNDWIX-YFKPBYRVSA-N L-homomethionine Chemical compound CSCCC[C@H](N)C(O)=O SFSJZXMDTNDWIX-YFKPBYRVSA-N 0.000 description 2
BXJJUEOXXQYQKK-UHFFFAOYSA-N acetic acid;2-amino-4-methylsulfanylbutanamide Chemical compound CC(O)=O.CSCCC(N)C(N)=O BXJJUEOXXQYQKK-UHFFFAOYSA-N 0.000 description 2
235000018417 cysteine Nutrition 0.000 description 2
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
229960003067 cystine Drugs 0.000 description 2
229940079919 digestives enzyme preparation Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
SFSJZXMDTNDWIX-UHFFFAOYSA-N homomethionine Natural products CSCCCC(N)C(O)=O SFSJZXMDTNDWIX-UHFFFAOYSA-N 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 description 1
GSYTVXOARWSQSV-SCSAIBSYSA-N (2r)-2-amino-4-methylsulfanylbutanamide Chemical compound CSCC[C@@H](N)C(N)=O GSYTVXOARWSQSV-SCSAIBSYSA-N 0.000 description 1
240000006439 Aspergillus oryzae Species 0.000 description 1
235000002247 Aspergillus oryzae Nutrition 0.000 description 1
241000228230 Aspergillus parasiticus Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
150000008574 D-amino acids Chemical class 0.000 description 1
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
241000187481 Mycobacterium phlei Species 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
241001603151 Philus Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
241000607269 Vibrio proteolyticus Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000000411 inducer Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229940055036 mycobacterium phlei Drugs 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

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
- 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
- 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)
Enzymes And Modification Thereof (AREA)

NL8800224A 1988-01-29 1988-01-29 Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren. NL8800224A (nl)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
NL8800224A NL8800224A (nl)	1988-01-29	1988-01-29	Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren.
EP89200154A EP0327156A1 (de)	1988-01-29	1989-01-26	Verfahren zur Herstellung von Schwefel enthaltenden L-alpha-Aminosäuren

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8800224A NL8800224A (nl)	1988-01-29	1988-01-29	Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren.
NL8800224		1988-01-29

Publications (1)

Publication Number	Publication Date
NL8800224A true NL8800224A (nl)	1989-08-16

Family

ID=19851681

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8800224A NL8800224A (nl)	1988-01-29	1988-01-29	Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren.

Country Status (2)

Country	Link
EP (1)	EP0327156A1 (de)
NL (1)	NL8800224A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0734453A1 (de) *	1993-12-17	1996-10-02	Dsm N.V.	Phenylserinamide und die herstellung von phenylserinen/phenylserinamiden

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU74142A1 (de) *	1976-01-08	1977-07-22

1988
- 1988-01-29 NL NL8800224A patent/NL8800224A/nl not_active Application Discontinuation
1989
- 1989-01-26 EP EP89200154A patent/EP0327156A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
EP0327156A1 (de)	1989-08-09

Legal Events

Date	Code	Title	Description
1989-08-16	A1B	A search report has been drawn up
1990-09-03	BV	The patent application has lapsed

Publication	Publication Date	Title
US4080259A (en)	1978-03-21	Process of preparing L and D α-amino acids by enzyme treatment of DL-α-amino acid amide
US20060051846A1 (en)	2006-03-09	Process for producing l-alpha-methylcysteine derivative
US4211840A (en)	1980-07-08	Method for producing D-α-amino acid
US5047585A (en)	1991-09-10	Process for racemizing an optically active N-benzylidene amino-acid amide
Soda et al.	2001	One-pot chemo-enzymatic enantiomerization of racemates
CN102203269B (zh)	2015-03-18	N-保护氨基酸的制造方法
US5219731A (en)	1993-06-15	Method for preparing optically-active amino acid derivatives
CA1258244A (en)	1989-08-08	PROCESS FOR THE PREPARATION OF L-.alpha.-AMINO ACID AND D- .alpha.-AMINO ACID AMIDE
JPH0785718B2 (ja)	1995-09-20	Ｄ−アミノ酸の製造方法
JPH0552195B2 (de)	1993-08-04
NL8800224A (nl)	1989-08-16	Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren.
Kamphuis et al.	1992	New developments in the synthesis of natural and unnatural amino acids
JP2670838B2 (ja)	1997-10-29	Ｌ―α―アミノ酸類の製造方法
Yamada	1993	Microbial reactions for the production of useful organic compounds
JPH0644870B2 (ja)	1994-06-15	Ｄ−α−アミノ酸の製造方法
JP4596098B2 (ja)	2010-12-08	光学活性α−アミノ酸の製造方法
JP2674078B2 (ja)	1997-11-05	Ｄ−α−アミノ酸の製造法
US4906572A (en)	1990-03-06	Method of culturing amino acid racemase-producing microorganism of genus pseudomonas
JP2674076B2 (ja)	1997-11-05	Ｄ−α−アミノ酸の製造方法
Yamada	1982	Enzymatic Processes for the Synthesis of Optically Active Amino Acids
US5212069A (en)	1993-05-18	Method of using N-acetyl-2,3-Didehydroleucine acylase for the preparation of D- or L-tryptophyl glycine, D- or L-tryptophyl-D-methionine or L-tryptophyl-D-cysteine
US5134073A (en)	1992-07-28	Microbiologically produced n-acetyl-2,3-didehydroleucine acylase
GB1577087A (en)	1980-10-15	Enzyme preparation having l-amino acyl amidase activity
JPS60184392A (ja)	1985-09-19	Ｄ−α−アミノ酸の製造方法
NL8702449A (nl)	1987-12-01	Werkwijze voor de bereiding van een d-alfa-aminozuur uit het overeenkomstige alfa-ketozuur.