JPH0146112B2 - - Google Patents

Info

Publication number: JPH0146112B2
Authority: JP; Japan
Prior art keywords: hydroxyisobutyric acid; genus; geotrichum; endomyces; microorganisms
Prior art date: 1980-08-21
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

JP11559280A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5739787A (en

Inventor

Masahiro Ogura

Shigeki Hamaguchi

Junzo Hasegawa

Hajime Kawarada

Kyoshi Watanabe

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.)

Kanegafuchi Chemical Industry Co Ltd

Original Assignee

Kanegafuchi Chemical Industry Co 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.)

1980-08-21

Filing date

1980-08-21

Publication date

1989-10-05

1980-08-21 Application filed by Kanegafuchi Chemical Industry Co Ltd filed Critical Kanegafuchi Chemical Industry Co Ltd

1980-08-21 Priority to JP11559280A priority Critical patent/JPS5739787A/ja

1982-03-05 Publication of JPS5739787A publication Critical patent/JPS5739787A/ja

1989-10-05 Publication of JPH0146112B2 publication Critical patent/JPH0146112B2/ja

Status Granted legal-status Critical Current

Links

241000159512 Geotrichum Species 0.000 claims description 22
241000178951 Endomyces Species 0.000 claims description 15
238000000034 method Methods 0.000 claims description 12
241000235648 Pichia Species 0.000 claims description 11
244000005700 microbiome Species 0.000 claims description 11
DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
241000235395 Mucor Species 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
241001467578 Microbacterium Species 0.000 claims description 7
241000192041 Micrococcus Species 0.000 claims description 7
241000222068 Sporobolomyces <Sporidiobolaceae> Species 0.000 claims description 7
241000223230 Trichosporon Species 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
244000168141 Geotrichum candidum Species 0.000 claims description 6
235000017388 Geotrichum candidum Nutrition 0.000 claims description 6
235000015097 nutrients Nutrition 0.000 claims description 6
241001509401 Gordonia rubripertincta Species 0.000 claims description 5
244000286779 Hansenula anomala Species 0.000 claims description 5
235000014683 Hansenula anomala Nutrition 0.000 claims description 5
241000221523 Rhodotorula toruloides Species 0.000 claims description 5
241000698291 Rugosa Species 0.000 claims description 4
238000012258 culturing Methods 0.000 claims description 4
241000352744 Magnusiomyces tetrasperma Species 0.000 claims description 3
241000187654 Nocardia Species 0.000 claims description 3
235000019441 ethanol Nutrition 0.000 claims description 3
241000894006 Bacteria Species 0.000 claims description 2
241000223252 Rhodotorula Species 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims description 2
235000014633 carbohydrates Nutrition 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
239000006285 cell suspension Substances 0.000 claims 1
239000012531 culture fluid Substances 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
230000000813 microbial effect Effects 0.000 claims 1
239000000725 suspension Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000001580 bacterial effect Effects 0.000 description 6
239000008103 glucose Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
241000235062 Pichia membranifaciens Species 0.000 description 4
229940041514 candida albicans extract Drugs 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000012138 yeast extract Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000222173 Candida parapsilosis Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000005273 aeration Methods 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
229940055022 candida parapsilosis Drugs 0.000 description 3
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005696 Diammonium phosphate Substances 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910000388 diammonium phosphate Inorganic materials 0.000 description 2
235000019838 diammonium phosphate Nutrition 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
-1 mannitrate Substances 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
229960001763 zinc sulfate Drugs 0.000 description 2
229910000368 zinc sulfate Inorganic materials 0.000 description 2
239000004254 Ammonium phosphate Substances 0.000 description 1
241001634940 Apiotrichum loubieri Species 0.000 description 1
241000222175 Diutina rugosa Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000150860 Hyphopichia burtonii Species 0.000 description 1
241000191953 Kocuria varians Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000228390 Sporobolomyces johnsonii Species 0.000 description 1
229920002472 Starch Polymers 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
241001634945 Trichosporon aquatile Species 0.000 description 1
239000000061 acid fraction Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 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
230000015572 biosynthetic process Effects 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229910021654 trace metal Inorganic materials 0.000 description 1
229930003231 vitamin Natural products 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

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

JP11559280A 1980-08-21 1980-08-21 Preparation of d(-)-beta-hydroxyisobutyric acid Granted JPS5739787A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP11559280A JPS5739787A (en)	1980-08-21	1980-08-21	Preparation of d(-)-beta-hydroxyisobutyric acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11559280A JPS5739787A (en)	1980-08-21	1980-08-21	Preparation of d(-)-beta-hydroxyisobutyric acid

Publications (2)

Publication Number	Publication Date
JPS5739787A JPS5739787A (en)	1982-03-05
JPH0146112B2 true JPH0146112B2 (fr)	1989-10-05

Family

ID=14666413

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11559280A Granted JPS5739787A (en)	1980-08-21	1980-08-21	Preparation of d(-)-beta-hydroxyisobutyric acid

Country Status (1)

Country	Link
JP (1)	JPS5739787A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3375024D1 (en) *	1982-03-16	1988-02-04	Kanegafuchi Chemical Ind	Process for producing d-beta-hydroxyalkanoic acid
EP0144832A3 (fr) *	1983-12-06	1987-01-21	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Procédé de production de dérivés optiquement actifs de l'acide 3-hydroxypropionique substitué en alpha
US5642953A (en) *	1993-11-02	1997-07-01	Mitsubishi Pencil Kabushiki Kaisha	Multiplex writing implement

1980
- 1980-08-21 JP JP11559280A patent/JPS5739787A/ja active Granted

Also Published As

Publication number	Publication date
JPS5739787A (en)	1982-03-05

Publication	Publication Date	Title
JPH0146112B2 (fr)	1989-10-05
US4310635A (en)	1982-01-12	Fermentative production of D(-)-β-hydroxyisobutyric acid
US4540665A (en)	1985-09-10	Process for producing D-β-hydroxyalkanoic acid
US5846793A (en)	1998-12-08	Microbial process for biotransformation to (R)-3-chloro-1,2-propanediol
EP0151419A2 (fr)	1985-08-14	Procédé de préparation de l'acide D(-)-bêta-hydroxyisobutyrique par fermentation
JP3146640B2 (ja)	2001-03-19	ベンゾイルギ酸の製造方法
US4981794A (en)	1991-01-01	Method of preparing D(-)-β-hydroxyisobutyric acid by fermentation
JPS6112678B2 (fr)	1986-04-09
JPS5953838B2 (ja)	1984-12-27	β−ヒドロキシ吉草酸の製造方法
JP4475407B2 (ja)	2010-06-09	微生物を利用した光学活性３−クロロ−２−メチル−１，２−プロパンジオールの製造方法
US3703439A (en)	1972-11-21	Process for the preparation of l-beta-(3,4-dihydroxyphenyl)-alpha-alanine by fermentation
US3297545A (en)	1967-01-10	Preparation and recovery of hydrogen
JPS6312288A (ja)	1988-01-19	光学活性（ｒ）−４−フエニル−２−ブタノ−ルの製造法
JPS5953839B2 (ja)	1984-12-27	（−）−α−ヒドロキシメチル酪酸の製造方法
JP3030916B2 (ja)	2000-04-10	βーグルコオリゴ糖の製造方法
JP2624296B2 (ja)	1997-06-25	γ−ハロ−β−ヒドロキシ酪酸エステルの製造法
JPS63188393A (ja)	1988-08-03	光学活性の２−ヒドロキシ酪酸誘導体の製造方法
KR840001150B1 (ko)	1984-08-11	D(-)-β-히드록시 이소부티릭산의 제조법
JP3178128B2 (ja)	2001-06-18	光学活性２，２，２−トリハロゲノ−１−フェニルエタノールの製造方法
JPS6112677B2 (fr)	1986-04-09
US5238828A (en)	1993-08-24	Method for the preparation of an optically active 2-substituted carboxylic acid
JP2902031B2 (ja)	1999-06-07	光学活性（ｓ）―３―フェニル―３―ヒドロキシプロピオン酸誘導体の製造方法
JPS5921600B2 (ja)	1984-05-21	Ｄ（−）−β−ヒドロキシイソ酪酸の製造方法
JPS6221509B2 (fr)	1987-05-13
JP2761064B2 (ja)	1998-06-04	光学活性１，３―ブタンジオールの製法