DE2050982C3 - - Google Patents

Info

Publication number: DE2050982C3
Authority: DE; Germany
Prior art keywords: acid; aminocyclohexylpenicillin; penicillin; atcc; salt
Prior art date: 1969-10-24
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.): Expired

Application number

DE19702050982

Other languages

German (de)

English (en)

Other versions

DE2050982A1 (de

DE2050982B2 (de

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.)

1969-10-24

Filing date

1970-10-16

Publication date

1977-06-02

1969-10-24 Priority claimed from JP44084653A external-priority patent/JPS4944351B1/ja

1970-10-16 Application filed filed Critical

1971-05-06 Publication of DE2050982A1 publication Critical patent/DE2050982A1/de

1976-10-14 Publication of DE2050982B2 publication Critical patent/DE2050982B2/de

1977-06-02 Application granted granted Critical

1977-06-02 Publication of DE2050982C3 publication Critical patent/DE2050982C3/de

Status Granted legal-status Critical Current

Links

JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 14
229960004244 cyclacillin Drugs 0.000 claims description 14
238000000034 method Methods 0.000 claims description 11
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 10
108090000790 Enzymes Proteins 0.000 claims description 10
102000004190 Enzymes Human genes 0.000 claims description 10
-1 Alkaline earth metal salt Chemical class 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
235000015097 nutrients Nutrition 0.000 claims description 7
229940056360 penicillin g Drugs 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 5
241000187653 Nocardia globerula Species 0.000 claims description 5
229930195708 Penicillin V Natural products 0.000 claims description 4
229940056367 penicillin v Drugs 0.000 claims description 4
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 4
241000588773 Kluyvera cryocrescens Species 0.000 claims description 3
241000187411 Streptomyces phaeochromogenes Species 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
125000005907 alkyl ester group Chemical group 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
239000002609 medium Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
210000005056 cell body Anatomy 0.000 description 6
239000012531 culture fluid Substances 0.000 description 6
244000005700 microbiome Species 0.000 description 6
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
239000000758 substrate Substances 0.000 description 6
229940041514 candida albicans extract Drugs 0.000 description 5
238000000855 fermentation Methods 0.000 description 5
230000004151 fermentation Effects 0.000 description 5
239000012138 yeast extract Substances 0.000 description 5
239000001888 Peptone Substances 0.000 description 4
108010080698 Peptones Proteins 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000007788 liquid Substances 0.000 description 4
235000019319 peptone Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
239000007979 citrate buffer Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
235000013372 meat Nutrition 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
229960003424 phenylacetic acid Drugs 0.000 description 3
239000003279 phenylacetic acid Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009395 breeding Methods 0.000 description 2
230000001488 breeding effect Effects 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
230000001954 sterilising effect Effects 0.000 description 2
238000004659 sterilization and disinfection Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
210000004748 cultured cell Anatomy 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 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
PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
MTPXRXOMKRLUMU-UHFFFAOYSA-N methyl 1-aminocyclohexane-1-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(N)CCCCC1 MTPXRXOMKRLUMU-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
MNAQQHWMIALRPQ-UHFFFAOYSA-N n,n-dimethylaniline;dihydrochloride Chemical compound Cl.Cl.CN(C)C1=CC=CC=C1 MNAQQHWMIALRPQ-UHFFFAOYSA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000005185 salting out Methods 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

DE19702050982 1969-10-24 1970-10-16 Verfahren zur herstellung von l-aminocyclohexylpenicillin Granted DE2050982B2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP44084653A JPS4944351B1 (es)	1969-10-24	1969-10-24
JP8465369		1969-10-24

Publications (3)

Publication Number	Publication Date
DE2050982A1 DE2050982A1 (de)	1971-05-06
DE2050982B2 DE2050982B2 (de)	1976-10-14
DE2050982C3 true DE2050982C3 (es)	1977-06-02

Family

ID=13836658

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19702050982 Granted DE2050982B2 (de)	1969-10-24	1970-10-16	Verfahren zur herstellung von l-aminocyclohexylpenicillin

Country Status (7)

Country	Link
US (1)	US3717548A (es)
JP (1)	JPS4944351B1 (es)
CA (1)	CA976099A (es)
CH (1)	CH553813A (es)
DE (1)	DE2050982B2 (es)
FR (1)	FR2070155B1 (es)
GB (1)	GB1320974A (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4135978A (en) *	1977-08-19	1979-01-23	Merck & Co., Inc.	Production of n-acyl-thienamycins

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3047467A (en) *	1957-08-02	1962-07-31	Beecham Res Lab	Process for the preparation of penicillins
US3553201A (en) *	1967-10-03	1971-01-05	American Home Prod	Dehydrated crystalline 6-(1-aminocyclo-alkylcarboxamido) penicillanic acids
DE1967074C3 (de) *	1968-09-18	1978-11-02	Kyowa Hakko Kogyo Co., Ltd., Tokio	Verfahren zur Herstellung von a-Aminobenzylpenicillin

1969
- 1969-10-24 JP JP44084653A patent/JPS4944351B1/ja active Pending
1970
- 1970-10-12 US US00080227A patent/US3717548A/en not_active Expired - Lifetime
- 1970-10-13 GB GB4864270A patent/GB1320974A/en not_active Expired
- 1970-10-15 CA CA095,676A patent/CA976099A/en not_active Expired
- 1970-10-16 DE DE19702050982 patent/DE2050982B2/de active Granted
- 1970-10-16 FR FR7037390A patent/FR2070155B1/fr not_active Expired
- 1970-10-19 CH CH1540070A patent/CH553813A/xx not_active IP Right Cessation

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DE3486277T2 (de)	1994-05-19	Verfahren zur Herstellung von Riboflavin.
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DE2152039C3 (de)	1974-06-12	Verfahren zur Herstellung von Bakterienzellmasse
DE2050982C3 (es)	1977-06-02
DE1945607C3 (de)	1975-07-03	Verfahren zur Herstellung von p-Amino benzylpenicillin
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DE2135246C3 (es)	1973-11-08
DE2050982B2 (de)	1976-10-14	Verfahren zur herstellung von l-aminocyclohexylpenicillin
DE2108404B2 (de)	1980-07-03	Verfahren zur Erzeugung von L-Arginin durch Mikroorganismen
DE2638024C2 (de)	1985-05-02	Verfahren zur Erhöhung der Cephamycin C-Ausbeute beim Züchten eines Cephamycin C erzeugenden Stammes der Gattung Streptomyces
DE2050983C3 (de)	1977-06-02	Verfahren zur Herstellung von alpha-Amino benzylpenicillin
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DE2318650C2 (de)	1982-11-25	Fermentative Herstellung von Deacetylcephalosporin C
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DE1277856B (de)	1968-09-19	Verfahren zur Herstellung von Uridylsaeure
DE1795721C2 (de)	1975-08-14	Verfahren zur fermentativen Herstellung von Orotidylsäure
DE1617586C (de)	1973-09-06	Verfahren zur biotechnischen HerT stellung von 6 Azaundm 5 phosphat
DE2153588C3 (de)	1979-05-31	Verfahren zur biotechnischen Herstellung von in 2-SteUung substituierten Adeninnueleotiden
DE1517837C (de)	1972-08-10	Verfahren zur biochemischen Herstellung von delta-(N-Acetyl)-L-Ornithin
DE2050983A1 (de)	1971-04-22	Verfahren zur Herstellung von alpha Amino benzylpenicillin
DE1770167C3 (de)	1975-10-16	Verfahren zur fermentativen Herstellung von Orotidylsäure
AT200724B (de)	1958-11-25	Verfahren zur Gewinnung von LLD-aktiven Substanzen der Vitamin B12-Gruppe
DE1966521C3 (de)	1978-01-05	Verfahren zur Herstellung von a-Aminobenzylpenicillin
DE2357100C3 (de)	1978-02-02	Verfahren zur biotechnischen Herstellung von L-Tryptophan