JPS6134797B2 - - Google Patents

Info

Publication number: JPS6134797B2
Authority: JP; Japan
Prior art keywords: medium; culture; olefin; added; hexadecene
Prior art date: 1978-02-10
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

JP1338678A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54107592A (en

Inventor

Hiromichi Oota

Hatsuki Tetsukawa

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.)

Sagami Chemical Research Institute

Original Assignee

Sagami Chemical Research Institute

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.)

1978-02-10

Filing date

1978-02-10

Publication date

1986-08-09

1978-02-10 Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute

1978-02-10 Priority to JP1338678A priority Critical patent/JPS54107592A/ja

1979-08-23 Publication of JPS54107592A publication Critical patent/JPS54107592A/ja

1986-08-09 Publication of JPS6134797B2 publication Critical patent/JPS6134797B2/ja

Status Granted legal-status Critical Current

Links

239000004711 α-olefin Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 13
241000894006 Bacteria Species 0.000 claims description 11
241000186216 Corynebacterium Species 0.000 claims description 8
241000158504 Rhodococcus hoagii Species 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 4
150000002118 epoxides Chemical class 0.000 claims 2
239000002609 medium Substances 0.000 description 47
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000002924 oxiranes Chemical class 0.000 description 12
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
230000003287 optical effect Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 6
SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 5
229920001817 Agar Polymers 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000008272 agar Substances 0.000 description 5
230000001580 bacterial effect Effects 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
238000011002 quantification Methods 0.000 description 5
229940041514 candida albicans extract Drugs 0.000 description 4
150000001875 compounds Chemical class 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
229920001214 Polysorbate 60 Polymers 0.000 description 3
230000009102 absorption Effects 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
238000012258 culturing Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
RVFPWBRPWOKUNQ-UHFFFAOYSA-N CCCCCCCCCCCCCCC(O)COC Chemical compound CCCCCCCCCCCCCCC(O)COC RVFPWBRPWOKUNQ-UHFFFAOYSA-N 0.000 description 2
229910052693 Europium Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000002306 biochemical method Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000012790 confirmation Methods 0.000 description 2
HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012546 transfer Methods 0.000 description 2
UKTHULMXFLCNAV-UHFFFAOYSA-N 2-hex-5-enyloxirane Chemical compound C=CCCCCC1CO1 UKTHULMXFLCNAV-UHFFFAOYSA-N 0.000 description 1
QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000011161 development Methods 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
SRYDOKOCKWANAE-UHFFFAOYSA-N hexadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCCC(O)O SRYDOKOCKWANAE-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
-1 methoxyl group Chemical group 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

JP1338678A 1978-02-10 1978-02-10 Preparation of optical active epoxide Granted JPS54107592A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP1338678A JPS54107592A (en)	1978-02-10	1978-02-10	Preparation of optical active epoxide

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1338678A JPS54107592A (en)	1978-02-10	1978-02-10	Preparation of optical active epoxide

Publications (2)

Publication Number	Publication Date
JPS54107592A JPS54107592A (en)	1979-08-23
JPS6134797B2 true JPS6134797B2 (cs)	1986-08-09

Family

ID=11831647

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1338678A Granted JPS54107592A (en)	1978-02-10	1978-02-10	Preparation of optical active epoxide

Country Status (1)

Country	Link
JP (1)	JPS54107592A (cs)

1978
- 1978-02-10 JP JP1338678A patent/JPS54107592A/ja active Granted

Also Published As

Publication number	Publication date
JPS54107592A (en)	1979-08-23

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