DK169561B1 - Anvendelse af Rhodococcus erythropolis-defektmutant Chol 149 K14 (DSM 2065) til mikrobiel nedbrydning af steroidforbindelser - Google Patents
Anvendelse af Rhodococcus erythropolis-defektmutant Chol 149 K14 (DSM 2065) til mikrobiel nedbrydning af steroidforbindelser Download PDFInfo
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- DK169561B1 DK169561B1 DK097182A DK97182A DK169561B1 DK 169561 B1 DK169561 B1 DK 169561B1 DK 097182 A DK097182 A DK 097182A DK 97182 A DK97182 A DK 97182A DK 169561 B1 DK169561 B1 DK 169561B1
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- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CVFYFDQTVDJOOT-UHFFFAOYSA-N hexan-1-ol;octan-1-ol Chemical compound CCCCCCO.CCCCCCCCO CVFYFDQTVDJOOT-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 229940124280 l-arginine Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 235000002908 manganese Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- RUVUHIUYGJBLGI-UHFFFAOYSA-N stigmast-4-en-3-one Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 RUVUHIUYGJBLGI-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (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)
- Steroid Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Description
i DK 169561 B1
Den foreliggende opfindelse angår anvendelsen af Rhodococcus erythropolis-defektmutant Chol 149 K14 (DSM 2065) til mikrobiel nedbrydning af steroidforbindelser.
5 Det er kendt, at visse mikroorganismer, især bestemte mikroor-ganisme-defektmutanter, danner hexahydroindanonderivater som interraediært nedbrydningsprodukt af steroidforbindelser. Således er det kendt, at en af Nocardia coralline IFO 3338 afledt utantstamme ud fra cholesterol danner bl.a. 3aa-H-4a-[3'-pro-10 pionsyre]-5a-hydroxy-7ap-methylhexahydro-l-indanon-6-lacton ed strukturformlen 15 6 7a 2 3 3a_3 (I) 2'^
20 O
(se T. Nakamatsu Agric. Biol. Chem. 44 (7), 1469-1474 (1980)). Som primært reaktionsprodukt af fermentationstrinet opstår 25 derved den tilhørende frie hydroxycarbonsyre 3-(5a-hydroxy- 7a/5-methyl-1-oxo-3aa-H-hexahydroindan-4a-yl)-propionsyre. Ved syrning af kulturopløsningen indeholdende dette nedbrydningsprodukt, f.eks. til en pH-værdi 2,0 eller derunder med svovlsyre, dannes den før anførte δ-lacton, jf r. FR-A1-2.387.288.
30 Andre forfattere beretter om omdannelsen af sitosterol, med en utant af Nocardia sp.M 29 til 3-(5a-hydroxy-7ap-methyl-l-oxo-3aa-H-hexahydroindan-4a-yl)-propionsyre, jfr. U. Sch'dmer . f1·, European J. Appl. Microbiol. Biotechnol., 10, 99 - 106 (1980). Andre henvisninger til dannelsen af dette partielle 35 nedbrydningsprodukt af steroler, især sitosterol, findes i de amerikanske patenter nr. 4.176.123 og 4.042.459 samt i tysk offentliggørelsesskrift nr. 2.746.323. Også for den mikro- DK 169561 B1 2 biel le nedbrydning af galdesyrer er påvist dannelsen af hexa-hydro-l-indanon-6-lactonen, jfr. f.eks. Nakamatsu m.f1., side 1473, og S. Hashimoto ro.fl., Biocem, J. 164, 715 (1977).
5 Den foreliggende opfindelse angår anvendelse af en hidtil ikke beskrevet mutant-stattime Chol 149 K 14, som blev isoleret ved UV behandling af den cholesterolnedbrydende vildstamme Chol 149, til mikrobiel nedbrydning af steroidforbindelser af dyrisk og vegetabilsk oprindelse i et vandigt næringsmedium under aerobe 10 betingelser til dannelse af 3-(5a-hydroxy-7a/3-methyl-l-oxo-3a/3-H-hexahydroindan-4a-yl) -propionsyre eller den tilsvarende δ-lactonforbindelse med den ovenfor anførte struktur. Den nye Rhodococcus erythropolis-defektmutant Chol 149-K14 er deponeret i den tyske samling af mikroorganismer (DSM), Griesebach-Strasse 15 8, D/3400, Gottingen, under deponeringsnummeret DSM 2065.
Defektmutanten DSM 2065 har vist sig særligt virkningsfuld til den partielle nedbrydning af naturlige steroidforbindelser, idet den giver et særligt højt udbytte. Egnede steroidudgangs-20 materialer til omdannelsen er naturlige steroler såsom cholesterol, sitosterol, sigmasterol og/eller ergosterol. Også derivater heraf såsom cholestenon, sitostenin, stigmastenon og lignende er egnede. Det samme gælder for galdesyrer såsom cholsyre, desoxycholsyre, 1 ithocholsyre og deres blandinger. 25 Men også andre forbindelser med steroidgrundstrukturen er egnede, f.eks. partielle nedbrydningsprodukter af naturlige steroler, hvori substituenten C 17 er blevet delvis eller fuldstændigt nedbrudt.
Den tekniske udførelse af nedbrydningsreaktionen sker på principielt kendt måde. Således kan f.eks. den som udgangsmateriale valgte steroidforbindelse sættes til mikroorganismekulturen under inkubationsperioden, eller den kan sættes til næringsmediet før podningen med defektmutanten. Der kan anvendes en steroidforbindelse eller en blanding af flere ste^ o 9 roidforbindelser. Fortrinsvis sættes steroiderne til kulturen i mængder på ca. 0,1 - 100 g pr. liter. Den optimale koncentration af steroidforbindelsen, som skal omdannes i dyrkningstrinet, kan konstateres ved simple forudgående forsøg. I almindelighed ligger koncentrationen af steroidfor- 3 DK 169561 B1 bindeisen i mediet fortrinsvis ikke over 50 g pr. liter og hyppigt ikke over 30 g pr. liter, men der foretrækkes dog mængder over 1 g pr. liter.
Det kan endvidere være at foretrække, at substratet, som 5 skal underkastes den partielle nedbrydning, ikke på én gang sættes til reaktionsmediet, men at denne tilsætning foretages gradvis i løbet af reaktionen. Fortrinsvis bliver udgangssubstratet i denne udførelsesform sat i det væsentlige kontinuerligt til reaktionsblandingen under nedbrydnings-10 reaktionens forløb. På denne måde kan udbyttet af det ønskede nedbrydningsprodukt forhøjes.
Kulturen dyrkes i et næringsmedium, der som kulstofkilde indeholder enten de steroidforbindelser, som skal omdannes, eller endvidere yderligere metaboliserbare kulstofkilder 15 såsom de sædvanlige af disse mikroorganismer krævede næringsstoffer og vækststøffer. Særligt gunstigt for væksten af mikroorganismerne er f.eks. paraffin, glycerol, carbonsyrer, stivelse, dekstrin, saccharose, glucose, fruktose og sukkerholdige affaldsstoffer. Egnede nitrogenkilder er ammonium-20 salte, nitrater, pepton, majsstøbevæske, sojamel, bærme og fiskemel. Endvidere kan der tilsættes fermentationsfremmende stoffer såsom gærekstrakt og vitaminer. Næringsmediet indeholder desuden sædvanligvis uorganiske salte såsom natrium-, kalium- eller ammoniumphosphater eller calcium-, magnium-, 25 mangan- og/eller jernsalte.
Emulgeringen af steroidudgangsmaterialet i næringsmediet sker fortrinsvis ved hjælp af kendte emulgatorer, f.eks. ved hjælp af fedtsyresorbitanestere eller deres ethylenoxidaddukter, polyoxyethylen, monolaurylether eller fedstyreamidoalkyl-30 betain.
Det anvendte kulturmedium bliver hensigtsmæssigt steriliseret ved opvarmning før begyndelsen af dyrkningen af mikroorganis- 4 DK 169561 B1 men. Efter afkøling og podning af kulturmediet med en egnet forkultur af defektmutanten inkuberes mellem 25 og 55°C, 5 fortrinsvis ved 27 - 30°C. Næringsopløsningens pH-værdi ligger mellem 4 og 8,5, fortrinsvis ved 6,8 - 8,0. Kulturen forsynes med oxygen ved rystning og omrøring eller gastilførsel og inkuberes fortrinsvis indtil nedbrydning af steroidforbindelsen til det ønskede trin. Nedbrydningen af steroid-10 forbindelsen kræver, alt efter substratkoncentration og andre fermentationsbetingelser, i reglen 24 - 160 timer. Medanven-delsé af bestemte inhibitorer eller væksthæmmere, der indskrænker mikroorganismevæksten, er ikke nødvendig.
15 Efter afbrydelse af fermentationen bliver cellemassen sædvanligvis skilt fra kulturvæsken, f.eks. ved filtrering, og det fremstillede produkt isoleret af kulturvæsken. Det har vist sig hensigtsmæssigt at syrne kulturvæsken til en pH-værdi på 2,0 eller derunder, eventuelt efter forudgående inddampning, 20 f.eks. i en tyndtlagsfordamper. Som produkt kan så umiddelbart udvindes hexahydro-l-indanon-6-lacton med formlen I. Til syrningen egner sig mineralsyrer, men også organiske syrer, og fortrinsvis syrnes med svovlsyre.
25 Den eventuelt inddampede og syrnede kulturvæske ekstraheres med et med vand ikke-blandbart opløsningsmiddel. Egnede opløsningsmidler er f.eks. methylisopropylketon, eddikesyre-ester, hexanol-n-octanol, n-hexan eller især halogenerede kulbrinteforbindelser såsom chloroform eller methylenchlorid.
3Q Efter inddampning af den organiske fase fremkommer reaktionsproduktet, som kan renses på sædvanlig måde, f.eks. ved krystallisation.
Den ifølge opfindelsen fremstillede hexahydro-l-iondanon-6- 35 lacton med formlen I eller den tilhørende frie substituerede propionsyreforbindelse er vigtige mellemprodukter til fremstilling af farmaceutisk aktive sterolforbindelser. De spiller især en betydelig rolle ved syntese af 19-norsteroider.
5 DK 169561 B1
EKSEMPEL
Stammen Choi 149/K14 (DSM 2065) dyrkes aerobt i en 75 liters forgæringsbeholder (fyldrumfang 50 liter) i følgende nærings-5 medium ved 30°C: 0,50 vægt% glucose, 0,5 vægts gærekstrakt, 0,80 vægts majsstøbevand, 10 1,50 vægts majsgluten, 0,13 vægts K2HPC>4, 0,09 vægtS (NH4) 2x, HP04, pH 7,0.
Efter 24 timers inkubation følger først tilsætning af 15 0,1 vægtS cholesterol sammen med 0,05 vægtS af et emulgeringsmiddel ("DK-ester P 50")
Efter yderligere 6 timer tilsættes i løbet af 36 timer 20 0,5 vægtS af emulgeringsmidlet plus 1,5 vægtS cholesterol plus 0,5 vægtS glucose.
25 Efter 124 timer afbrydes fermentationen, cellemassen frafil-treres, den cellefri kulturvæske koncentreres i tyndtlags-fordamper 3:1, koncentratet indstilles med vandig svovlsyre til pH 0,2 og ekstraheres til slut med methylenchlorid i rumfangsforholdet 1:1. Methylenchloridfasen fraskilles. Efter 30 inddampning af den organiske fase fremkommer 3aa-H-4a-[3'- propionsyre] -5a-hydroxy-7a3-methylhexahydro-l-indanon- δ-laet on i et udbytte på ca. 63 molS.
Den ifølge opfindelsen anvendte mikroorganisme (DSM 2065) er 35 af DSM (Deutsche Sammlung von Mikroorganismen) blevet identificeret som Rhodococcus erythropolis på grundlag af følgende fysiologiske og kemotaxonomiske undersøgelser.
6 DK 169561 B1
Kolonistruktur og farve:
Kolonierne udviser ved vækst på GC-Agar (Merck) en mat, svagt foldet overflade. Konsistensen er fast. Der dannes intet luftmycelium. Kolonierne er ikke påfaldende farvede. Farvetonen 5 ligger ved 1014 (elfenben i RAL farvetavlen eller ca. 2 i Ost-walds farvetavle). Ifølge Seilers kodning (1983) hører koloniform og farve til kode (11) (perlehvid gullig).
Mikroskopi: 10 Unge kulturer danner korte, lidet forgrenede hyfer, som hurtigt henfalder til koklignende elementer.
Kemotaxonomi:
Mycolsyretyper 15 DSM nr. Corynemycolsyre C/N nocardomylcolsyre mycolsyre sensu stric· 2065 +
Pyrolyseprodukter af mycolsyremethylester (MAMES = methylsyre-methylester).
2 0
Opvarmer man MSME (methylsyremethylester) over 280°C sker der en spaltning til et aldehyd med en fedtsyremethylester (FAMES). Brudstykkerne er af taxonomisk betydning.
DSM nr. 12:0 14:1 14:0 16:1 16:0 18:1 18:0 (FAMES i %) 25 2065 12 2 29 5 45 3 4
Procentuel fordeling af fedtsyrer fra Hercelle-hydrolysater DSM nr. mættede forgrenede anteiso umættede 30 iso forgrenede 10-methyl 2065 14 .16 18 15 17 14 16 18 15 17 15 17 16 18 17 16 18 17 3 47 1 1 12 11 25 1
Procentisk fordeling af menachinoner af rensede celleekstrakter 7 DK 169561 B1 DSM nr. 7/10 7/2 7/4 8/0 8/2 8/4 8/6 9/0 9/2 9/4 9/6 9/8 10/0 10/2 10/4 10/6 2065 1 93 tr 6 tr
Fysiologi 5 C-kilde bedømme!sesspektrum til differentiering af coryneforme organismer med kortkædede mycolsyrer (C eller N), MK-8 (H2) og tuberkulostearinsyre (10-Me).
10 OMS nr. N-val SuccS Adip S Citr S Gluc S Leu Asp AspS D-Rib l-ara 2065(11) + + + + (+)+ + +(+)- DSM nr. Adenin tyrosin capryl. fermentativt 2065 + - 15 kolonifarve, fysiologi og udbredelse af specifikke lipider hos - 00r-yneforme-organismer med mycolsyre.
20 25 1 35 8 DK 169561 B1 OSH nr. Mycolsy- 10- Mena- fysiol. farve retype MSl Pyrol2 meth chinon type type C-18
Bacterionema ma- 5 truchotti C 32,34 14 16 18 - 9/2 ? ? 20 297 Brevibacterium divaricatum C 34 36 14 - 9/2 El 20 20 300 Corynebact.
glutamaticum C 26-38 - 9/2 El 20 10 20 170 Corynebact.
xerosis C 28-36 14 16 - 9/2 F V 50 20 306 Brevib.ammoniagenes C 35 36 14 16 + 9/2 E II 21 20 132 Arthrobacter variabilis C + 9/2 A VI 10 15 20 536 Caseobacter polymorphus C 14 + ? A VI 10 20 582 Corynebacterium bovis C 24-3 8,10 + 8/2 ? 52 20 131 C. fascians C/N 39-50 12-18 + 8/2 A I 41 20
Identificering af DSH 2065 C/N 14 16 + 8/2 A II 11 43 066 Rhodococcus erythropolis C/N 36-48 12-18 + 8/2 A II 60 25 43 241 Rh. rhodochrous C/N 38-48 12-18 + 8/2 A III 71 43 349 Rh. equi C/N 28-36 12-18 + 8/2 A IV 70 43 248 Rh. Coprophilus C/N 38-50 12-18 + 8/2 A VII 70r 43 248 Rh. corallinus N 52-64 16,18 + 9/2 A V 70r 43 197 Rh. rubropertinctus N 38-64 12-18 + 9/2 A V 70r 30 43 587 Noc. amarae N 46-54 16:1,18:1 -i- 9/2 ?
Nocardia s.s. N 46-65 14 16 + 8/4 A rest 70r 20 162 C.paurometabolum N 72:2 20 22 + 9 B rest 10 43 246 "Gordona aurantiaca" H 68-74 20,22 + 9 A rest 52
Mycobacterium s.s. M 70-90 22-26 + 9/2 C = Corynemycolsyrer, N = Nocardomycosyrer, M = Mycolsyre s.s.
8/2 = MK8(H2) Menachinon med en isoprenylkade på 8 enheder, en er måttet, LM * luftmycelium.
35 9 DK 169561 B1 1) = mycolsyrelængde angivet i C-atomer.
2} = frigjort ved pyrolytisk spaltning af mycolsyremethyleste-regelmæssig.
5 Kode til kolonifarve hos coryneforme organismer (Seiler 1983)
Type Kolonifarve RAL beskrivelse Ral nr.
10 hvid perlehvid 1013 11 hvid til gullig perlehvid til - 1013 til - 10 12 hvid med brun midte perlehvid og beige 1013+ 20 citrongul svovlgul 1016 21 klar gul zinkgul 1018 30 gul-orange kadmiumgul 1021 31 gul-orange, blå afsnit kadmiumgul 1021 15 32 gul-orange kadmiumgul til kromgul 1021/1007 33 gul-orange kromgul 1007 34 gul-orange kromgul til safrangul 1007/1017 * 40 orange,s ,K0Hreaktion+ve safrangul 1017 * 41 orange,r ,KOHreaktion+ve safrangul 1017 20 42 orange, KOH reaktion-ve safrangul 1017 50 flødefarvet til beige lys elfenben til sandgul 1015- 51 beige beige 1001 52 beige-brun brunbeige 1011 53 gulbrun honninggul 1005 25 60 fløde til rosa til beige 70 gulrød til rød pastelorange til ren orange 2003- 71 beige-rød beigerød 3012 72 rødviolet gammelrosa 3014 80 blå blå 5009 30 90 grå, gennemskinnelig gråhvid 9002 91 gul, gennemskinnelig *) * s, glat kolonioverflade; r, ru kolonioverflade; - ingen bekvem farve.
C-kilde udnyttelsesspektrum til differentiering af coryneforme organismer med kortksdede mycolsyrer (C eller N) og tuberkulo-stearinsyre.
35 10 DK 169561 B1 N-Val SuccS AdipS CitrS GlucS Leu Asp AspS D-rib L-Arg AI C.fascians (41 O 100 O 100 100 100 93 80 93 93 N corynebact (70) ID DSM 2065 (11) + + + + + + + + (+) 5 All R.erythrop (60) 100 100 100 100 94 100 94 10 74 0 AIII "rhodoc (70,71) 48 100 78 87 22 96 0 0 4 0 AIV "equi (70) 6 100 0 0 0 0 0 0 82 0 AV "corall (70) o 100 0 100 86 0 0 14 0 0 "rubropert (70r) 10 "terrae (70p) AVI A variabi 1 (10) 71 100 0 100 86 0 29 86 0 0 AVII C alkanolyt(60) 00 0 0 0 66 000 0 R coprophil (70r) 15 C-kilde udnyttelsesspektrum af andre coryneforme organismer med kortkædede mycolsyrer 10-Me Valerat Citrat D-Gluco m-Inosit Tyr Aden anaer C-18 20 El C glutamam (20,21) - 0 92 100 96 0 nd 84
Eli Br ammoniag(10,21)+ 0 86 0 86 100 nd 0 FV C xerosis (50)- 80 0 0 0 0 nd 100 ID DSM 2065 (11) + nd + + nd + (+) - 25 Nøgle til differentiering af mycolsyreholdige coryneforme mikroorganismer ved hjælp af kemotaxonomisk kendetegn.
Mycolsyretyper hos coryneforme organismer
30 C C/N N M
Corynebacterium Rhodococcus Rhodococcus Mycobacterium
Corynebacterium Nocardia C.paurometabulum "Cordona aurantiaca 35 DK 169561 B1 11
Mycolsyretype C (C24-C36)
Tubereol usteari nsyre ikke til stede til stede 5 MK-9 (H2) MK-8(H2) HK-9(H2)
Ba.matruchotii C.bovis (52) Br.ammon i agenes (10)E II
Br.divaricatum (20) El A.variabilis (10) A IV
C.glutamaticum (20) El C-xerosis (50) FV
10
Mycolsyretype C/N (C30-C50) eller N(C45-C65) (Tuberculosestearinsyre altid til stede)
C/N N
15 MK-8(H2) MK-9(H2) MK-8(H4)
R.equi (70) A IV R.bronchial is (41) N.asteroides (70r)+U
C.fascians (41) A I R.corallinus (70r) A V N.brasi1iensis(41r)+l N.calcarea (60)A II R.coprophilius(70r) A VII N.oditis.caviarum LM R.erythropolis(60)A II R.rubropect.(70r)A V N.brevicatena LM 20 DSM 2065 (!!) A II R.terrae (70r) A V R.rhodochrous(71)A III N.amarae R.rhodnil (60)
R.rubrus (71) A III N.globerula (70) A III 25 N.restricts (70) A IV
Mycolsyretype M (C60-C90) (Tuberculostearinsyre altid til stede) 30 MK-9 MK-9(H2)
Corynebacterium paurometabolum (10) B Mycobacterium
"Gordons aurantiaca" A
LM = luftmycelium; A,B fysiologiske typer, () kolonitype 35
Claims (1)
- DK 169561 B1 Anvendelse af Rhodococcus erythropolis-defektmutant Chol 149 K14 (DSM 2065) til mikrobiel nedbrydning af steroidforbindelser af 5 dyrisk og vegetabilsk oprindelse i et vandigt næringsmedium under aerobe betingelser til dannelse af 3ao:-H-4Qf-[3/-propion-syre]-5a-hydroxy-7a/S-methylhexahydro-l-indanon eller dens δ-lacton. 10
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3113053 | 1981-04-01 | ||
| DE19813113053 DE3113053A1 (de) | 1981-04-01 | 1981-04-01 | Verfahren zur herstellung eines tricyclischen steroid-abbauprodukts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK97182A DK97182A (da) | 1982-10-02 |
| DK169561B1 true DK169561B1 (da) | 1994-11-28 |
Family
ID=6129005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK097182A DK169561B1 (da) | 1981-04-01 | 1982-03-05 | Anvendelse af Rhodococcus erythropolis-defektmutant Chol 149 K14 (DSM 2065) til mikrobiel nedbrydning af steroidforbindelser |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4784953A (da) |
| EP (1) | EP0061687B1 (da) |
| JP (1) | JPS57208995A (da) |
| AT (1) | ATE12948T1 (da) |
| DE (2) | DE3113053A1 (da) |
| DK (1) | DK169561B1 (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4923403A (en) * | 1984-08-16 | 1990-05-08 | South African Inventions Development Corp. | Microbiological process for degradation of steroids |
| IL119649A (en) * | 1995-11-30 | 2002-03-10 | Akzo Nobel Nv | Preparation of Cyclic Kills of History - 3 keto- (5) 10, (-9) 11 steroidadians |
| US6595259B2 (en) | 2001-01-09 | 2003-07-22 | Premark Fef L.L.C. | Vacuum actuated label applying wand |
| CN104496958A (zh) * | 2014-11-28 | 2015-04-08 | 江西赣亮医药原料有限公司 | 一种膜法提取a环降解物的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304860A (en) * | 1975-11-17 | 1981-12-08 | The Upjohn Company | Process for the microbial transformation of steroids |
| US4042459A (en) * | 1975-11-17 | 1977-08-16 | The Upjohn Company | Composition of matter and process |
| US4062729A (en) * | 1976-11-26 | 1977-12-13 | The Upjohn Company | Microbial transformation of steroids |
| US4097335A (en) * | 1977-02-14 | 1978-06-27 | The Upjohn Company | Microbial transformation of steroids |
| JPS53130492A (en) * | 1977-04-15 | 1978-11-14 | Satoru Arima | Production of indane compound by microorganism |
| US4176123A (en) * | 1978-01-30 | 1979-11-27 | The Upjohn Company | Steroid intermediates |
| US4329432A (en) * | 1978-02-13 | 1982-05-11 | The Upjohn Company | Mycobacterium fortuitum strain |
-
1981
- 1981-04-01 DE DE19813113053 patent/DE3113053A1/de not_active Withdrawn
-
1982
- 1982-03-05 DK DK097182A patent/DK169561B1/da not_active IP Right Cessation
- 1982-03-22 EP EP82102355A patent/EP0061687B1/de not_active Expired
- 1982-03-22 DE DE8282102355T patent/DE3263227D1/de not_active Expired
- 1982-03-22 AT AT82102355T patent/ATE12948T1/de not_active IP Right Cessation
- 1982-03-31 JP JP57051453A patent/JPS57208995A/ja active Granted
-
1984
- 1984-06-14 US US06/620,537 patent/US4784953A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK97182A (da) | 1982-10-02 |
| EP0061687A1 (de) | 1982-10-06 |
| EP0061687B1 (de) | 1985-04-24 |
| JPS57208995A (en) | 1982-12-22 |
| DE3263227D1 (en) | 1985-05-30 |
| JPH0453508B2 (da) | 1992-08-26 |
| DE3113053A1 (de) | 1982-10-21 |
| ATE12948T1 (de) | 1985-05-15 |
| US4784953A (en) | 1988-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |