JPH02119785A - Production of 2-oxo-4-phenylbutyric acid - Google Patents
Production of 2-oxo-4-phenylbutyric acidInfo
- Publication number
- JPH02119785A JPH02119785A JP27386788A JP27386788A JPH02119785A JP H02119785 A JPH02119785 A JP H02119785A JP 27386788 A JP27386788 A JP 27386788A JP 27386788 A JP27386788 A JP 27386788A JP H02119785 A JPH02119785 A JP H02119785A
- Authority
- JP
- Japan
- Prior art keywords
- phenylbutyric acid
- oxo
- acid
- hydroxy
- genus
- Prior art date
- 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
Links
- PPKAIMDMNWBOKN-UHFFFAOYSA-N 2-Oxo-4-phenylbutyric acid Chemical compound OC(=O)C(=O)CCC1=CC=CC=C1 PPKAIMDMNWBOKN-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 244000005700 microbiome Species 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- JNJCEALGCZSIGB-UHFFFAOYSA-N 2-hydroxy-4-phenylbutanoic acid Chemical compound OC(=O)C(O)CCC1=CC=CC=C1 JNJCEALGCZSIGB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 241000193830 Bacillus <bacterium> Species 0.000 claims abstract description 4
- 241000186216 Corynebacterium Species 0.000 claims abstract description 4
- 241001467578 Microbacterium Species 0.000 claims abstract description 4
- 241000186146 Brevibacterium Species 0.000 claims abstract description 3
- 241000186063 Arthrobacter Species 0.000 claims abstract 2
- 230000001580 bacterial effect Effects 0.000 claims description 17
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 abstract description 2
- 229960005025 cilazapril Drugs 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000000813 microbial effect Effects 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- QYCBZFRDGXIZIP-UHFFFAOYSA-N 2-hydroxy-2-phenylbutanoic acid Chemical compound CCC(O)(C(O)=O)C1=CC=CC=C1 QYCBZFRDGXIZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 239000002609 medium Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 229950009215 phenylbutanoic acid Drugs 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000186226 Corynebacterium glutamicum Species 0.000 description 1
- JAGZUIGGHGTFHO-UHFFFAOYSA-N Ethyl 3-phenylpropanoate Chemical compound CCOC(=O)CCC1=CC=CC=C1 JAGZUIGGHGTFHO-UHFFFAOYSA-N 0.000 description 1
- 241000144155 Microbacterium ammoniaphilum Species 0.000 description 1
- 101100161696 Myxine glutinosa ache gene Proteins 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- GYBMSOFSBPZKCX-UHFFFAOYSA-N sodium;ethanol;ethanolate Chemical compound [Na+].CCO.CC[O-] GYBMSOFSBPZKCX-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 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
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、２−オキソ−４−フェニル酪酸の製造方法に
関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing 2-oxo-4-phenylbutyric acid.
２−オキソ−４−フェニル酪酸は、種々の医薬品の原料
として有用である。たとえは、そのエチルエステルは、
アンジオテンシン交換酵素の阻害剤として、有効な血圧
降下剤であるシラザプリルの原料となる（Ｊ、 Ｃｌ１
ｅｎ１． Ｓｏｃ、 ＰｅｒｋｉｎＴｒａｎｓ、 Ｉ
、 １０１１ （１９８６））。2-oxo-4-phenylbutyric acid is useful as a raw material for various pharmaceuticals. For example, the ethyl ester is
As an angiotensin exchange enzyme inhibitor, it is the raw material for cilazapril, an effective antihypertensive agent (J, Cl1
en1. Soc, PerkinTrans, I
, 1011 (1986)).
〈従来の技術〉
従来、２−オキソ−４−フェニル酪酸の製造方法として
は、３−フェニルプロピオン酸エチルエステルと蓚酸エ
チル、２８％ナトリウムエトキシドエタノール溶液から
化学合成により製造する方法（特開昭５７−１７９１．
４１号公報）が知られている。<Prior art> Conventionally, 2-oxo-4-phenylbutyric acid has been produced by chemical synthesis from 3-phenylpropionate ethyl ester, ethyl oxalate, and a 28% sodium ethoxide ethanol solution (Japanese Patent Application Laid-open No. 57-1791.
No. 41) is known.
〈発明が解決しようとする課題〉
しかし、従来の方法は操作が煩雑で、収率が悪く工業的
に有利な方法とはいい姐い。<Problems to be Solved by the Invention> However, the conventional methods are complicated to operate and have poor yields, making them not industrially advantageous.
く課題を解決するだめの手段および作用〉本発明者らは
、２−オキソ−４−フェニル酪酸の製造方法を種々検討
した結果、微生物の有する酸化力を利用して、安価に合
成できる２−ヒドロキシ−４−フェニル酪酸を、２−オ
キソ−４−フェニル酪酸に、有利に導き得ることを見出
し、本発明に至った。微生物を利用して、２−ヒドロキ
シ−４−フェニル酪酸から２−オキソ−４−フェニル酪
酸を蓄積さぜることは、従来知られておらず、かつ行わ
れていない。Means and action for solving the problems> As a result of studying various methods for producing 2-oxo-4-phenylbutyric acid, the present inventors found that 2-oxo-4-phenylbutyric acid can be synthesized at low cost by utilizing the oxidizing power of microorganisms. It was discovered that hydroxy-4-phenylbutyric acid can be advantageously converted into 2-oxo-4-phenylbutyric acid, leading to the present invention. It has not been known or practiced to accumulate 2-oxo-4-phenylbutyric acid from 2-hydroxy-4-phenylbutyric acid using microorganisms.
すなわち、本発明は、２−ヒドロキシ−４−フェニル酪
酸を２−オキソ−４−フェニル酪酸へ変換する能力を有
し、かつコリネバクテリウム（ＣＯ「ｙｎｃｂａｃｔｅ
ｒｉｕｍ）属、ブレビバクテリウム（３ｒｅｖｉｂａｃ
ｔｅｒｉｕＩＩｌ）属、ミクロバクテリウム（Ｈｉｃｒ
ｏｂａｃｔｅｒｉｕｌｌ）属、アースロバフタ−（Ａｒ
ｔｈｒｏｂａｃｔｅｒ）属またはバチルス（Ｂａｃｉ
ｌ １ｕｓ）属に属する微生物より選ばれた少なくとも
１種の微生物の培養物、菌体またはその処理物を、２−
ヒドロキシ−４−フェニル酪酸に作用させて２−オキソ
−４−フェニル酪酸を生成蓄積せしめ、反応液から２−
オキソ−４−フェニル酪酸を単離採取することを特徴と
する２−オオキソー４−フェニル酪酸の製造方法である
。That is, the present invention has the ability to convert 2-hydroxy-4-phenylbutyric acid to 2-oxo-4-phenylbutyric acid, and
genus Brevibacterium (3 revibac
teriuIIl), Microbacterium (Hicr
obacteriull), Arthrobacterium (Ar
throbacter genus or Bacillus
A culture, a bacterial cell, or a processed product of at least one microorganism selected from microorganisms belonging to the genus 2-
2-oxo-4-phenylbutyric acid is produced and accumulated by acting on hydroxy-4-phenylbutyric acid, and 2-oxo-4-phenylbutyric acid is produced and accumulated from the reaction solution.
This is a method for producing 2-oxo-4-phenylbutyric acid, which comprises isolating and collecting oxo-4-phenylbutyric acid.
以下、本発明の構成を詳細に説明する。Hereinafter, the configuration of the present invention will be explained in detail.
本発明で原料として使用する２−ヒドロキシ４−フェニ
ル酪酸はＲ体、８体、ラセミ体のいずれでもよい。通常
は工業的に有利なラセミ体を用いる。The 2-hydroxy 4-phenylbutyric acid used as a raw material in the present invention may be any of the R form, 8 form, and racemic form. Usually, a racemate is used because it is industrially advantageous.
本発明においては、２−しドロキシ−４−フェニル酪酸
を２−オキソ−４−フェニル酪酸へ変換する能力を有し
、コリネバクテリウム属、ブレビバクテリウム属、アー
スロバフタ−属、ミクロバクテリウム属またはバチルス
属に属する微生物より選ばれた少なくとも１！ｌ！の微
生物を用いる。The present invention has the ability to convert 2-droxy-4-phenylbutyric acid to 2-oxo-4-phenylbutyric acid, and has the ability to convert 2-droxy-4-phenylbutyric acid into 2-oxo-4-phenylbutyric acid, At least 1 selected from microorganisms belonging to the genus Bacillus! l! microorganisms are used.
かかる微生物の具体例としては、たとえは、コリネバク
テリウム・タルタミカムＡＴＣＣ１３０３２、コリネバ
クテリウム・アセ１〜アシドフイラムＡ”ＦＣＣ１３８
７０、ブレビバクテリウム・ラクトファーメンタムＡＴ
ＣＣ１３，８６９、アース！７バクター・シ１−レウス
ＡＴＣＣ１１６２４、ミクロバクテリウム・アンモニア
フイラムＡ ＴＣＣ１５３５４、バチルス・スブチリス
ＡＴＣＣ６０５１か挙げられる。Specific examples of such microorganisms include Corynebacterium tartamicum ATCC13032, Corynebacterium ace1 to Acidophyllum A"FCC138
70. Brevibacterium lactofermentum AT
CC13,869, Earth! 7 Bacterium ci1-reus ATCC 11624, Microbacterium ammoniaphilum A TCC 15354, and Bacillus subtilis ATCC 6051.
これらの微生物の培養には、通常これらの菌が責化しう
る有機および無機の炭素源、窒素源およびビタミン、ミ
ネラルなどを適宜配合した培地を用いる。培地のＰ Ｈ
は、通常Ｐ Ｈ５〜９が好ましい。温度は通常２０〜４
０℃で、菌は通常１〜７日間、好気的に培養ずれはよい
。For culturing these microorganisms, a medium containing appropriate organic and inorganic carbon sources, nitrogen sources, vitamins, minerals, etc. that can be used by these microorganisms is usually used. PH of medium
Usually, pH is preferably 5 to 9. Temperature is usually 20-4
At 0°C, the bacteria are normally cultured aerobically for 1 to 7 days.
本発明の反応においては、これらの微生物の培養物、菌
体まなはその処理物を用いる。好ましくは菌体懸濁液ま
たは、菌体処理物を用いる。ここでいう菌体懸濁液とは
、培養して得られた菌体を遠心分離取得したもので、菌
体処理物とは、培養して得られた菌体を超音波処理した
ものや、たとえは公知の方法によりアクリルアミドゲル
担体などに固定化したものか挙げられる。In the reaction of the present invention, cultures of these microorganisms, bacterial cells, or processed products thereof are used. Preferably, a bacterial suspension or a treated bacterial cell suspension is used. The bacterial cell suspension referred to here refers to the bacterial cells obtained by culturing and centrifuging them, and the bacterial cell processed material refers to the bacterial cells obtained by culturing with ultrasonic treatment, An example of this is immobilization on an acrylamide gel carrier or the like by a known method.
反応基質である２−しドロキシ−４−フェニル酪酸の反
応液中での濃度は、通常０．１〜５％程度用いることが
できる。添加方法に関しては、−括あるいは分割添加の
どちらでもよい。The concentration of 2-droxy-4-phenylbutyric acid, which is a reaction substrate, in the reaction solution can generally be about 0.1 to 5%. Regarding the addition method, it may be added all at once or in parts.
反応温度は、通常２０〜４０″Ｃ１好ましくは２５〜３
５°Ｃである。反応液のｐ Ｈは、通常５〜１１０、好
ましくは７．５〜９０に保たれる。反応時間は反応温度
によって異なるが、通常３０’Ｃで３０〜９０時間であ
る。The reaction temperature is usually 20-40" C1, preferably 25-3
It is 5°C. The pH of the reaction solution is generally maintained at 5-110, preferably 7.5-90. The reaction time varies depending on the reaction temperature, but is usually 30 to 90 hours at 30'C.
反応方式としては、培養終了液に基質を添加し、好気的
に振とうする方法と、菌体懸濁液あるいは菌体処理物に
基質を添加し、好気的に振とうする方法かあり、どちら
も採用可能であるか後者の方か良好な結果を与−える。There are two reaction methods: one is to add a substrate to the cultured solution and shake it aerobically, and the other is to add a substrate to the bacterial suspension or treated bacterial cell mixture and shake it aerobically. Both methods are possible, or the latter gives better results.
かくして、本発明の反応により、２−ヒドロキシ−４−
フェニル酪酸は酸化され、２−オキソ４−フェニル酪酸
か生成する。Thus, by the reaction of the present invention, 2-hydroxy-4-
Phenylbutyric acid is oxidized to produce 2-oxo4-phenylbutyric acid.
かくして生成した２−オキソ−４−フェニル酪酸を反応
液から単離するには、一般的な分離精製方法を用いれは
よい。たとえば、分収用液クロカラムを用いて、分取す
る方法またはフェニルヒドラゾン化して、単離する方法
など目的物を単離採取できる。In order to isolate the 2-oxo-4-phenylbutyric acid thus produced from the reaction solution, a general separation and purification method may be used. For example, the target product can be isolated and collected using a liquid chromatography column for fractionation, or by converting it into phenylhydrazonation and isolating it.
〈実施例〉
以下、実施例によって、本発明の詳細な説明するか、本
発明はこれらの実施例のみに限定されるものではない。<Examples> Hereinafter, the present invention will be explained in detail with reference to Examples, but the present invention is not limited only to these Examples.
なお、実施例中、２−オキソ−４−フェニル酪酸の生成
量は、ＯＤＳカラムを用い高速液体クロマトグラフィー
（１（Ｐ Ｌ Ｃ）で分析した。In the examples, the amount of 2-oxo-4-phenylbutyric acid produced was analyzed by high performance liquid chromatography (1 (PLC)) using an ODS column.
また、実施例中、収率は減少基質に対する生成しな２−
オキソ−４−フェニル酪酸のモル％で表わず。In addition, in the examples, the yield was reduced due to the lack of 2-
Not expressed as mol% of oxo-4-phenylbutyric acid.
実施例１
クルコース４％、ポリペプトン２％、酵母エキシ０５％
、リン酸二水素カリウム０５％よりなる液体培地を苛性
ソータ水溶液でｐ Ｈ７，０とし、１８−聞φ試験管に
５ｍｌずつ分注し、オートクレーブ中】２０°Ｃで２０
分間加熱滅菌した。ここに斜面培地から第１表に示す各
種の菌を１白金耳ずつ接種し、２８°Ｃで６３時間振と
う機上で好気的に培養した。その後、遠心分離により菌
体を分離し水で１度洗浄して菌体を調整して得られた菌
体を１０ｇ／ぶのラセミ体の２−ヒドロキシ−４−フェ
ニル酪酸水溶液５＋ｎｌの入った］、８ｎ＋ｍφ試験管
に添加し、２８°Ｃで４０時間ｐ Ｈ７，０”ｒ振とう
し反応した。このようにして得られた反応液を遠心分離
し、その上清をＨＰ Ｌ Ｃで分析した結果を第１表に
示す。Example 1 Cucose 4%, Polypeptone 2%, Yeast Extract 05%
A liquid medium consisting of 05% potassium dihydrogen phosphate was adjusted to pH 7.0 with a caustic sorter aqueous solution, dispensed in 5 ml portions into 18-diameter test tubes, and incubated at 20°C for 20 minutes in an autoclave.
Heat sterilized for minutes. One platinum loopful of each type of bacteria shown in Table 1 was inoculated from the slant culture medium and cultured aerobically on a shaker at 28°C for 63 hours. Thereafter, the bacterial cells were separated by centrifugation and washed once with water to prepare the bacterial cells. was added to an 8n+mφ test tube and reacted at 28°C for 40 hours with shaking at pH 7.0"r.The reaction solution thus obtained was centrifuged, and the supernatant was analyzed by HPLC. The results are shown in Table 1.
第 １ 表
※ＯＰＢ ： ２−オキソ−４−フェニル酪酸実施例２
実施例１と同様の液体培地を、５００ （ＤＩの坂ロフ
ラスコに１００ ｍｌ入れ、オートクレーブ中１２０°
Ｃで２０分間加熱滅菌しな。ここに斜面培地からミクロ
バクテリウム・アンモニアフィラム（ＡＴＣＣ１５３５
４’）を１白金耳接種し、２８°Ｃで６３時間振とぅ機
上で、好気的に培養した。その後、遠心分離により菌体
を分離し、水で１度洗浄して菌体を調整し、得られた菌
体を２０ ｇ ／ Ｊのラセミ体２−ヒドロキシ−４フ
エニル酪酸水溶液１００＋ｎｌに添加し、３０℃で２５
時間、ｐ Ｈ７，５で振とうし反応した。この反応液を
遠心分離し、菌体を除いな上清を１１ＰＬＣ（’ｊ７’
ム：３１（ｇｅｌｏＤＳ １２ＯＡ５５ｎ＋＋ｎＸ６
０■）で分取し、目的物の２−オキソ−４−フェニル酪
酸を６００■得たく単離収率６３２％）。Table 1 *OPB: 2-oxo-4-phenylbutyric acid Example 2 Pour 100 ml of the same liquid medium as in Example 1 into a Sakalo flask at 500 ml (DI) and heat at 120° in an autoclave.
Heat sterilize at C for 20 minutes. Here, Microbacterium ammoniaphyllum (ATCC1535
4') was inoculated into one platinum loop and cultured aerobically at 28°C for 63 hours on a shaker. Thereafter, the bacterial cells were separated by centrifugation, washed once with water to prepare the bacterial cells, and the obtained bacterial cells were added to 100+ nl of a 20 g/J racemic 2-hydroxy-4 phenylbutyric acid aqueous solution. 25 at 30℃
The mixture was shaken and reacted at pH 7.5 for an hour. This reaction solution was centrifuged, and the supernatant without bacterial cells was purified by 11PLC ('j7'
Mu: 31 (geloDS 12OA55n++nX6
The target product, 2-oxo-4-phenylbutyric acid, was collected in an isolated yield of 632%.
〈発明の効果〉
本発明によれは、２−ヒドロキシ−４−フェニル酪酸か
ら２−オキソ−４−フェニル酪酸を、微生物を用いた酸
化反応により温和な条件下で効率よく生産できる。<Effects of the Invention> According to the present invention, 2-oxo-4-phenylbutyric acid can be efficiently produced from 2-hydroxy-4-phenylbutyric acid under mild conditions by an oxidation reaction using microorganisms.
Claims (1)
フェニル酪酸へ変換する能力を有し、かつコリネバクテ
リウム（Ｃｏｒｙｎｅｂａｃｔｅｒｉｕｍ）属、ブレビ
バクテリウム（Ｂｒｅｖｉｂａｃｔｅｒｉｕｍ）属、ミ
クロバクテリウム（Ｍｉｃｒｏｂａｃｔｅｒｉｕｍ）属
、アースロバクター（Ａｒｔｈｒｏｂａｃｔｅｒ）属ま
たはバチルス（Ｂａｃｉｌｌｕｓ）属に属する微生物よ
り選ばれた少なくとも１種の微生物の培養物、菌体また
はその処理物を、２−ヒドロキシ−４−フェニル酪酸に
作用させて２−オキソ−４−フェニル酪酸を生成蓄積せ
しめ、反応液から２−オキソ−４−フェニル酪酸を単離
採取することを特徴とする２−オキソ−４−フェニル酪
酸の製造方法。2-Hydroxy-4-phenylbutyric acid to 2-oxo-4-
having the ability to convert into phenylbutyric acid, and belonging to the genus Corynebacterium, genus Brevibacterium, genus Microbacterium, genus Arthrobacter, or genus Bacillus; A culture, a bacterial cell, or a treated product of at least one microorganism selected from among microorganisms is allowed to act on 2-hydroxy-4-phenylbutyric acid to produce and accumulate 2-oxo-4-phenylbutyric acid, and the resulting product is extracted from the reaction solution. A method for producing 2-oxo-4-phenylbutyric acid, which comprises isolating and collecting 2-oxo-4-phenylbutyric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27386788A JPH0661270B2 (en) | 1988-10-28 | 1988-10-28 | Method for producing 2-oxo-4-phenylbutyric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27386788A JPH0661270B2 (en) | 1988-10-28 | 1988-10-28 | Method for producing 2-oxo-4-phenylbutyric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02119785A true JPH02119785A (en) | 1990-05-07 |
| JPH0661270B2 JPH0661270B2 (en) | 1994-08-17 |
Family
ID=17533667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27386788A Expired - Lifetime JPH0661270B2 (en) | 1988-10-28 | 1988-10-28 | Method for producing 2-oxo-4-phenylbutyric acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0661270B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006021558A (en) * | 2004-07-06 | 2006-01-26 | Wire Device:Kk | Monitoring system |
-
1988
- 1988-10-28 JP JP27386788A patent/JPH0661270B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006021558A (en) * | 2004-07-06 | 2006-01-26 | Wire Device:Kk | Monitoring system |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0661270B2 (en) | 1994-08-17 |
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