JPH0151998B2 - - Google Patents

Info

Publication number: JPH0151998B2
Authority: JP; Japan
Prior art keywords: acid; salt; reaction; cholic acid; ketocholic
Prior art date: 1985-06-07
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

JP60122769A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61282099A (ja

Inventor

Satoshi Tsuzuki

Fujimaro Ogata

Yoshihiko Murata

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.)

Resonac Holdings Corp

Original Assignee

Showa Denko KK

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.)

1985-06-07

Filing date

1985-06-07

Publication date

1989-11-07

1985-06-07 Application filed by Showa Denko KK filed Critical Showa Denko KK

1985-06-07 Priority to JP12276985A priority Critical patent/JPS61282099A/ja

1986-12-12 Publication of JPS61282099A publication Critical patent/JPS61282099A/ja

1989-11-07 Publication of JPH0151998B2 publication Critical patent/JPH0151998B2/ja

Status Granted legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 claims description 44
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[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 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 42
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 39
239000004380 Cholic acid Substances 0.000 claims description 38
229960002471 cholic acid Drugs 0.000 claims description 38
235000019416 cholic acid Nutrition 0.000 claims description 38
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 29
244000005700 microbiome Species 0.000 claims description 25
239000000872 buffer Substances 0.000 claims description 16
241000192041 Micrococcus Species 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 6
230000001580 bacterial effect Effects 0.000 claims description 5
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
235000015097 nutrients Nutrition 0.000 claims 1
MIHNUBCEFJLAGN-DMMBONCOSA-N 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanic acid Chemical compound C([C@H]1C[C@H]2O)[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(=O)C1 MIHNUBCEFJLAGN-DMMBONCOSA-N 0.000 description 28
238000000034 method Methods 0.000 description 23
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 12
229960002645 boric acid Drugs 0.000 description 12
235000010338 boric acid Nutrition 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000004327 boric acid Substances 0.000 description 11
239000002609 medium Substances 0.000 description 11
108090000790 Enzymes Proteins 0.000 description 10
102000004190 Enzymes Human genes 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000006227 byproduct Substances 0.000 description 9
241000894006 Bacteria Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229960001091 chenodeoxycholic acid Drugs 0.000 description 3
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[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)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 3
229940099352 cholate Drugs 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000008103 glucose Substances 0.000 description 3
230000000813 microbial effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 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
239000007853 buffer solution Substances 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000012258 culturing Methods 0.000 description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
239000011790 ferrous sulphate Substances 0.000 description 2
235000003891 ferrous sulphate Nutrition 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
229940099596 manganese sulfate Drugs 0.000 description 2
239000011702 manganese sulphate Substances 0.000 description 2
235000007079 manganese sulphate Nutrition 0.000 description 2
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000011002 quantification Methods 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[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)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 description 2
229960001661 ursodiol Drugs 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
CSWRFCISTSMAHQ-FYRHABGPSA-N (5S,8S,9S,10R,13S,14S,17R)-16,16-dihydroxy-13-methyl-17-[(2R)-pentan-2-yl]-1,2,3,4,5,6,7,8,9,11,12,14,15,17-tetradecahydrocyclopenta[a]phenanthrene-10-carboxylic acid Chemical compound C([C@H]1CC2)CCC[C@]1(C(O)=O)[C@@H]1[C@@H]2[C@@H]2CC(O)(O)[C@H]([C@H](C)CCC)[C@@]2(C)CC1 CSWRFCISTSMAHQ-FYRHABGPSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 1
241000186063 Arthrobacter Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
229930006000 Sucrose Natural products 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
235000011054 acetic acid Nutrition 0.000 description 1
238000005273 aeration Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 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
125000005619 boric acid group Chemical group 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000731 choleretic agent Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
208000001130 gallstones Diseases 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000010813 internal standard method Methods 0.000 description 1
239000013028 medium composition Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
238000011017 operating method Methods 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 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
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004457 water analysis Methods 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)
Steroid Compounds (AREA)

JP12276985A 1985-06-07 1985-06-07 １２−ケト−３α，７α−ジヒドロキシコラン酸の製造方法 Granted JPS61282099A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP12276985A JPS61282099A (ja)	1985-06-07	1985-06-07	１２−ケト−３α，７α−ジヒドロキシコラン酸の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP12276985A JPS61282099A (ja)	1985-06-07	1985-06-07	１２−ケト−３α，７α−ジヒドロキシコラン酸の製造方法

Publications (2)

Publication Number	Publication Date
JPS61282099A JPS61282099A (ja)	1986-12-12
JPH0151998B2 true JPH0151998B2 (de)	1989-11-07

Family

ID=14844157

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP12276985A Granted JPS61282099A (ja)	1985-06-07	1985-06-07	１２−ケト−３α，７α−ジヒドロキシコラン酸の製造方法

Country Status (1)

Country	Link
JP (1)	JPS61282099A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5451510A (en) *	1991-10-24	1995-09-19	Tokyo Tanabe Company, Limited	Process for preparing 3α, 7α-dihydroxy-12-keto-5β-cholanic acid using bacillus spp. FERM BP-3394 and FERM BP-3397

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59120098A (ja) *	1982-12-28	1984-07-11	Showa Denko Kk	１２−ケト−３α，７α−ジヒドロキシコラン酸の製造法

1985
- 1985-06-07 JP JP12276985A patent/JPS61282099A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59120098A (ja) *	1982-12-28	1984-07-11	Showa Denko Kk	１２−ケト−３α，７α−ジヒドロキシコラン酸の製造法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5451510A (en) *	1991-10-24	1995-09-19	Tokyo Tanabe Company, Limited	Process for preparing 3α, 7α-dihydroxy-12-keto-5β-cholanic acid using bacillus spp. FERM BP-3394 and FERM BP-3397

Also Published As

Publication number	Publication date
JPS61282099A (ja)	1986-12-12

Publication	Publication Date	Title
JPS5937951B2 (ja)	1984-09-12	アミドの生物学的製造法
HU200752B (en)	1990-08-28	Process for producing 6-hydroxynicotinic acid in biological way
JPH0928390A (ja)	1997-02-04	グリコール酸の微生物学的製造法
JPH0151998B2 (de)	1989-11-07
JPH09154589A (ja)	1997-06-17	エリスリトールの製造方法
CA1119981A (en)	1982-03-16	Process for preparing 2,5-diketogluconic acid
JPS5923794B2 (ja)	1984-06-05	ジヒドロキシアセトンの製造法
JPS58201992A (ja)	1983-11-25	微生物によるβ−置換プロピオン酸またはそのアミドの製造法
JP3705046B2 (ja)	2005-10-12	微生物による光学活性４−ハロゲノ−１，３−ブタンジオール及びその誘導体の製法
JPS592693A (ja)	1984-01-09	アミドの生物学的製造法
JPH04304893A (ja)	1992-10-28	微生物による含窒素複素環化合物の水酸化物の製造方法
JPH0591895A (ja)	1993-04-16	Ｄ−セリンの製造法
JP4061862B2 (ja)	2008-03-19	微生物によるクロロヒドリンの光学分割法
JP2624296B2 (ja)	1997-06-25	γ−ハロ−β−ヒドロキシ酪酸エステルの製造法
JPH01104194A (ja)	1989-04-21	Ｄ−（−）−酒石酸の製造法
JP3011472B2 (ja)	2000-02-21	酵素法によるインジゴの製造法
JP2901458B2 (ja)	1999-06-07	ゲンチアノースの製造方法
JPH01171478A (ja)	1989-07-06	ロドコッカス属細菌の培養方法
JPH04197189A (ja)	1992-07-16	アミドの生物学的製造方法
JPH01102094A (ja)	1989-04-19	高温下でのリバビリンの製造方法
JPH0851989A (ja)	1996-02-27	マレイン酸の異性化方法
JPS5953838B2 (ja)	1984-12-27	β−ヒドロキシ吉草酸の製造方法
JPS5816692A (ja)	1983-01-31	酵素によるｌ−トリプトフアンの製造方法
KR910007857B1 (ko)	1991-10-02	생물전환에 의한 하이드로코티손으로부터 프레드니솔론의 제조방법
JPH0424992B2 (de)	1992-04-28

JPH0151998B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=14844157

Family Applications (1)

Country Status (1)

Cited By (1)

Citations (1)

Patent Citations (1)

Cited By (1)

Also Published As

Similar Documents