CS230551B2 - Method of hydrolysis of racemic hydantoins to optical active amino acide derivative - Google Patents

Method of hydrolysis of racemic hydantoins to optical active amino acide derivative Download PDF

Info

Publication number: CS230551B2
Authority: CS; Czechoslovakia
Prior art keywords: hydrolysis; reaction; derivative; culture; carried out
Prior art date: 1977-03-15

Application number

CS781612A

Other languages

Czech (cs)

English (en)

Inventor

Aurelio Viglia

Eugenio Fascetti

Elena Perricone

Ludwig Degen

Original Assignee

Anic Spa

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.)

1977-03-15

Filing date

1978-03-14

Publication date

1984-08-13

1978-03-14 Application filed by Anic Spa filed Critical Anic Spa

1984-08-13 Publication of CS230551B2 publication Critical patent/CS230551B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 18
230000007062 hydrolysis Effects 0.000 title claims abstract description 17
238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 17
150000001469 hydantoins Chemical class 0.000 title claims abstract description 5
230000003287 optical effect Effects 0.000 title description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
102000004190 Enzymes Human genes 0.000 claims abstract description 13
108090000790 Enzymes Proteins 0.000 claims abstract description 13
244000005700 microbiome Species 0.000 claims abstract description 12
238000006243 chemical reaction Methods 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
229910052500 inorganic mineral Chemical class 0.000 claims 1
239000011707 mineral Chemical class 0.000 claims 1
229940091173 hydantoin Drugs 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 4
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract description 3
230000003301 hydrolyzing effect Effects 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 3
150000001413 amino acids Chemical class 0.000 abstract description 2
241001112741 Bacillaceae Species 0.000 abstract 1
235000001014 amino acid Nutrition 0.000 abstract 1
210000004027 cell Anatomy 0.000 description 20
239000001963 growth medium Substances 0.000 description 13
102000004157 Hydrolases Human genes 0.000 description 8
108090000604 Hydrolases Proteins 0.000 description 8
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 7
239000008363 phosphate buffer Substances 0.000 description 7
230000001580 bacterial effect Effects 0.000 description 6
239000000872 buffer Substances 0.000 description 6
230000007071 enzymatic hydrolysis Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
241000149420 Bothrometopus brevis Species 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000011534 incubation Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229920001817 Agar Polymers 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000008272 agar Substances 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
235000013372 meat Nutrition 0.000 description 4
239000002609 medium Substances 0.000 description 4
230000001954 sterilising effect Effects 0.000 description 4
238000004659 sterilization and disinfection Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000001888 Peptone Substances 0.000 description 3
108010080698 Peptones Proteins 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000002255 enzymatic effect Effects 0.000 description 3
239000000411 inducer Substances 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
235000019319 peptone Nutrition 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
230000000284 resting effect Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
108700023418 Amidases Proteins 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
239000002028 Biomass Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
102000005922 amidase Human genes 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
GIOUOHDKHHZWIQ-UHFFFAOYSA-N 2-(carbamoylamino)-2-phenylacetic acid Chemical compound NC(=O)NC(C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-UHFFFAOYSA-N 0.000 description 1
241000304886 Bacilli Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
210000000712 G cell Anatomy 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 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
KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical compound NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
241000364057 Peoria Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003698 anagen phase Effects 0.000 description 1
229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309466 calf Species 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical class OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000013311 vegetables Nutrition 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y10S435/833—Bacillus brevis

Landscapes

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

CS781612A 1977-03-15 1978-03-14 Method of hydrolysis of racemic hydantoins to optical active amino acide derivative CS230551B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT21232/77A IT1075132B (it)	1977-03-15	1977-03-15	Complessi enzimatici atti a trasformare idantoine raceme in amminoacidi otticamente attivi e loro applicazioni

Publications (1)

Publication Number	Publication Date
CS230551B2 true CS230551B2 (en)	1984-08-13

Family

ID=11178761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS781612A CS230551B2 (en)	1977-03-15	1978-03-14	Method of hydrolysis of racemic hydantoins to optical active amino acide derivative

Country Status (22)

Country	Link
US (1)	US4248967A (fr)
JP (1)	JPS53115890A (fr)
AU (1)	AU519192B2 (fr)
BE (1)	BE864935A (fr)
CA (1)	CA1113871A (fr)
CH (1)	CH636078A5 (fr)
CS (1)	CS230551B2 (fr)
DD (1)	DD141683A5 (fr)
DE (1)	DE2811303C3 (fr)
DK (1)	DK113578A (fr)
FR (1)	FR2383961A1 (fr)
GB (1)	GB1566088A (fr)
HU (1)	HU181488B (fr)
IL (1)	IL54185A (fr)
IT (1)	IT1075132B (fr)
LU (1)	LU79217A1 (fr)
NL (1)	NL7802819A (fr)
NO (1)	NO148153C (fr)
SE (1)	SE7802949L (fr)
SU (1)	SU1124889A3 (fr)
YU (1)	YU60778A (fr)
ZA (1)	ZA781447B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3031151A1 (de) *	1980-08-18	1982-04-15	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von d-n-carbamoyl-(alpha)-aminosaeuren und mikroorganismen dafuer
IT1209495B (it) *	1984-02-02	1989-08-30	A San Donato Milanese Milano	Procedimento per la preparazione di l-alfa-amminoacidi.
US5283182A (en) *	1986-09-17	1994-02-01	Beecham Group Plc	Preparation of immobilized hydantoinase stabilized with divalent metal ions
ATE94906T1 (de) *	1989-01-02	1993-10-15	Ruetgerswerke Ag	Verfahren zur herstellung von l-alphaaminos\|uren.
DE3918057C1 (fr) *	1989-06-02	1990-05-03	Degussa Ag, 6000 Frankfurt, De
US5962279A (en) *	1994-06-24	1999-10-05	Kanegafuchi Kagaku Kogyo Kabushiki Kaisha	Process for producing D-amino acids with composite immobilized enzyme preparation
FR2728905A1 (fr) *	1994-12-29	1996-07-05	Rhone Poulenc Nutrition Animal	Nouvelle acide amine amidohydrolase, sequence nuclotidique correspondant et leurs utilisations
US6121024A (en) *	1997-07-17	2000-09-19	Sudge; Sandhya Suresh	Halophilic Pseudomonas strain having accession No.NCIM 5109 (ATCC 55940) and a process for preparingD(-)N-carbamoylphenylglycine using said strain

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT987278B (it) *	1973-05-11	1975-02-20	Snam Progetti	Procedimento per la preparazione di l carbamil ammino acidi e dei corrispondenti l amminoacidi
US4065353A (en) *	1975-05-12	1977-12-27	Snamprogetti, S.P.A.	Method for the preparation of D-carbamyl aminoacids and the corresponding D-aminoacids
IT1039757B (it) *	1975-07-10	1979-12-10	Snam Progetti	Complessi enzimatici atti a trasformare idantoine raceme in am minoacidi otticamente attivi e loro applicazione
US4094741A (en) *	1976-02-04	1978-06-13	Kanegafuchi Kagaku Kogyo Kabushiki Kaisha	Process for preparing D-(-)-N-carbamoyl-2-(phenyl or substituted phenyl)glycines

1977
- 1977-03-15 IT IT21232/77A patent/IT1075132B/it active
1978
- 1978-03-01 AU AU33704/78A patent/AU519192B2/en not_active Expired
- 1978-03-03 IL IL54185A patent/IL54185A/xx unknown
- 1978-03-10 US US05/885,194 patent/US4248967A/en not_active Expired - Lifetime
- 1978-03-13 LU LU79217A patent/LU79217A1/fr unknown
- 1978-03-13 NO NO780882A patent/NO148153C/no unknown
- 1978-03-13 ZA ZA00781447A patent/ZA781447B/xx unknown
- 1978-03-13 DD DD78204139A patent/DD141683A5/de unknown
- 1978-03-13 FR FR7807196A patent/FR2383961A1/fr active Granted
- 1978-03-13 GB GB9896/78A patent/GB1566088A/en not_active Expired
- 1978-03-14 CA CA298,914A patent/CA1113871A/fr not_active Expired
- 1978-03-14 YU YU00607/78A patent/YU60778A/xx unknown
- 1978-03-14 CS CS781612A patent/CS230551B2/cs unknown
- 1978-03-14 HU HU78SA3098A patent/HU181488B/hu unknown
- 1978-03-14 CH CH277678A patent/CH636078A5/it not_active IP Right Cessation
- 1978-03-14 DK DK113578A patent/DK113578A/da not_active Application Discontinuation
- 1978-03-14 SE SE7802949A patent/SE7802949L/xx unknown
- 1978-03-15 BE BE185968A patent/BE864935A/fr not_active IP Right Cessation
- 1978-03-15 NL NL7802819A patent/NL7802819A/xx not_active Application Discontinuation
- 1978-03-15 SU SU782589348A patent/SU1124889A3/ru active
- 1978-03-15 JP JP2878178A patent/JPS53115890A/ja active Pending
- 1978-03-15 DE DE2811303A patent/DE2811303C3/de not_active Expired

Also Published As

Publication number	Publication date
ZA781447B (en)	1979-02-28
DD141683A5 (de)	1980-05-14
CH636078A5 (it)	1983-05-13
DE2811303C3 (de)	1981-05-21
HU181488B (en)	1983-07-28
US4248967A (en)	1981-02-03
IL54185A (en)	1981-09-13
NL7802819A (nl)	1978-09-19
JPS53115890A (en)	1978-10-09
NO148153C (no)	1983-08-17
NO780882L (no)	1978-09-18
CA1113871A (fr)	1981-12-08
GB1566088A (en)	1980-04-30
AU3370478A (en)	1979-10-18
NO148153B (no)	1983-05-09
SE7802949L (sv)	1978-09-16
AU519192B2 (en)	1981-11-19
DE2811303A1 (de)	1978-09-21
IL54185A0 (en)	1978-06-15
DK113578A (da)	1978-09-16
IT1075132B (it)	1985-04-22
YU60778A (en)	1982-10-31
DE2811303B2 (de)	1980-07-31
FR2383961B1 (fr)	1980-08-29
BE864935A (fr)	1978-09-15
FR2383961A1 (fr)	1978-10-13
SU1124889A3 (ru)	1984-11-15
LU79217A1 (fr)	1978-06-28

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US4814272A (en)	1989-03-21	Process for the biotechnical production of rhamnolipids including rhamnolipids with only one β-hydroxydecanoic acid residue in the molecule
US4762788A (en)	1988-08-09	Process for producing cellulolytic enzymes
FI66021C (fi)	1984-08-10	Enzymatiskt foerfarande foer framstaellning av optiskt aktiva d-aminosyror ur motsvarande hydantoiner eller rasemiska karbamoylderivat
US4774179A (en)	1988-09-27	Process for preparing a 7-aminocephalosporanic acid compound
US3945888A (en)	1976-03-23	Method for the production of cephalosporins
US4111749A (en)	1978-09-05	Method of converting racemic hydantoins into optically active aminoacids
US3749641A (en)	1973-07-31	Production of 7-amino-3-methylcephem compounds
CS230551B2 (en)	1984-08-13	Method of hydrolysis of racemic hydantoins to optical active amino acide derivative
EP0299558A1 (fr)	1989-01-18	Procédé de préparation d'ibuprofène
JPH022396A (ja)	1990-01-08	セファロスポリンｃ及び類似体の一段階酵素反応による７‐アミノセファロスポラン酸及びその類似体への変換
US4985364A (en)	1991-01-15	Preparation of cyclopropanecarboxylic acids
FI70596B (fi)	1986-06-06	Foerfarande foer enzymatisk hydrolysering av raffinos
US4533632A (en)	1985-08-06	Production of a cephalosporin by fermentation
US4340672A (en)	1982-07-20	Enzymatic synthesis of β-lactam antibacterials
US4237227A (en)	1980-12-02	Process for preparing D-N-carbamoyl-α-amino acids
EP0332379B1 (fr)	1996-08-14	Procédé de préparation de L-alpha-acides aminés
US4141790A (en)	1979-02-27	Process for the preparation of 7-amino-cephem compounds using mold fungi
US5108914A (en)	1992-04-28	Process for the synthesis of l-alpha-amino acids
D'Amato et al.	1976	A chemically defined medium for cephalosporin C production by Paecilomyces persicinus
KR100264740B1 (ko)	2000-10-02	글루탐산을 생산하는 미생물 및 이를 이용한 글루탐산의 제조방법
CZ847388A3 (en)	1997-12-17	Use of gamma-glutamyl transpeptidase for hydrolysis of alpha-aminoadipinylmonoamino compounds
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