JPS62198400A - 微生物による３−オキソ−１，４−プレグナジエン−２０−カルボン酸の製造法 - Google Patents

微生物による３−オキソ−１，４−プレグナジエン−２０−カルボン酸の製造法

Info

Publication number: JPS62198400A
Authority: JP; Japan
Prior art keywords: corynebacterium; carboxylic acid; oxo; medium; culture
Prior art date: 1986-02-27
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.): Granted

Application number

JP4022986A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0566118B2 (cs

Inventor

Mitsugi Iida

飯田　貢

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

PAAMAKEMU ASIA KK

Permachem Asia Ltd

Original Assignee

PAAMAKEMU ASIA KK

Permachem Asia Ltd

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.)

1986-02-27

Filing date

1986-02-27

Publication date

1987-09-02

1986-02-27 Application filed by PAAMAKEMU ASIA KK, Permachem Asia Ltd filed Critical PAAMAKEMU ASIA KK

1986-02-27 Priority to JP4022986A priority Critical patent/JPS62198400A/ja

1987-09-02 Publication of JPS62198400A publication Critical patent/JPS62198400A/ja

1993-09-21 Publication of JPH0566118B2 publication Critical patent/JPH0566118B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 8
244000005700 microbiome Species 0.000 title abstract description 6
OZESBBVMFLIODA-VJFOQZSSSA-N 2-[(8s,9s,10r,13s,14s,17r)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]propanoic acid Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(C)C(O)=O)[C@@]1(C)CC2 OZESBBVMFLIODA-VJFOQZSSSA-N 0.000 title abstract 2
241000186216 Corynebacterium Species 0.000 claims abstract description 27
229940076810 beta sitosterol Drugs 0.000 claims abstract description 8
LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims abstract description 8
NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims abstract description 8
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims abstract description 8
229950005143 sitosterol Drugs 0.000 claims abstract description 8
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BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims description 7
SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 7
235000000431 campesterol Nutrition 0.000 claims description 7
238000012258 culturing Methods 0.000 claims description 4
-1 oxo-1,4-pregnadiene-20-carboxylic acid Chemical compound 0.000 claims description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
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239000000843 powder Substances 0.000 abstract description 2
150000003839 salts Chemical class 0.000 abstract description 2
VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 abstract 1
238000004440 column chromatography Methods 0.000 abstract 1
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239000002609 medium Substances 0.000 description 20
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 8
239000008103 glucose Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000008272 agar Substances 0.000 description 3
239000002738 chelating agent Substances 0.000 description 3
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229910052760 oxygen Inorganic materials 0.000 description 3
241000252203 Clupea harengus Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
230000001580 bacterial effect Effects 0.000 description 2
RUVUHIUYGJBLGI-XJZKHKOHSA-N beta-sitostenone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 RUVUHIUYGJBLGI-XJZKHKOHSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000002532 enzyme inhibitor Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
235000019514 herring Nutrition 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000011160 research Methods 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
241000186031 Corynebacteriaceae Species 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
KYOFIJXMVNQYFC-UHFFFAOYSA-N beta-sitostenone Natural products C1C=C2CC(=O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 KYOFIJXMVNQYFC-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229910001429 cobalt ion Inorganic materials 0.000 description 1
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940125532 enzyme inhibitor Drugs 0.000 description 1
QQIOPZFVTIHASB-UHFFFAOYSA-N ergost-4-en-3-one Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCC(C)C(C)C)C1(C)CC2 QQIOPZFVTIHASB-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
238000009630 liquid culture Methods 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000010355 oscillation Effects 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000011002 quantification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
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239000003270 steroid hormone Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
235000003702 sterols 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
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

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Preparation Of Compounds By Using Micro-Organisms (AREA)

JP4022986A 1986-02-27 1986-02-27 微生物による３−オキソ−１，４−プレグナジエン−２０−カルボン酸の製造法 Granted JPS62198400A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP4022986A JPS62198400A (ja)	1986-02-27	1986-02-27	微生物による３−オキソ−１，４−プレグナジエン−２０−カルボン酸の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4022986A JPS62198400A (ja)	1986-02-27	1986-02-27	微生物による３−オキソ−１，４−プレグナジエン−２０−カルボン酸の製造法

Publications (2)

Publication Number	Publication Date
JPS62198400A true JPS62198400A (ja)	1987-09-02
JPH0566118B2 JPH0566118B2 (cs)	1993-09-21

Family

ID=12574907

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4022986A Granted JPS62198400A (ja)	1986-02-27	1986-02-27	微生物による３−オキソ−１，４−プレグナジエン−２０−カルボン酸の製造法

Country Status (1)

Country	Link
JP (1)	JPS62198400A (cs)

1986
- 1986-02-27 JP JP4022986A patent/JPS62198400A/ja active Granted

Also Published As

Publication number	Publication date
JPH0566118B2 (cs)	1993-09-21

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