JPH09276A - Decomposition method for carboxylic acid derivatives - Google Patents
Decomposition method for carboxylic acid derivativesInfo
- Publication number
- JPH09276A JPH09276A JP15070995A JP15070995A JPH09276A JP H09276 A JPH09276 A JP H09276A JP 15070995 A JP15070995 A JP 15070995A JP 15070995 A JP15070995 A JP 15070995A JP H09276 A JPH09276 A JP H09276A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- acid derivative
- alcaligenes
- group
- hydrogen atom
- 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.)
- Pending
Links
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
(57)【要約】
【目的】 本発明は、カルボン酸誘導体（I）を資化す
る能力を有する微生物の培養液、菌体又は菌体処理物を
利用してカルボン酸誘導体（I）を分解する方法を提供
する。
【構成】 次式（I）：
【化１】
（式中、Ｒ1は水素原子又はアルカリ金属原子を表し、
Ｒ2及びＲ3は同一又は相異なり、水素原子又はメチル基
を表し、Ｘはアミノ基、ヒドロキシ基又はメトキシ基を
表す。）で示されるカルボン酸誘導体を、アルカリゲネ
ス属に属し、該カルボン酸誘導体を資化する能力を有す
る微生物の培養液、菌体又は菌体処理物で処理すること
を特徴とするカルボン酸誘導体の分解法。
【効果】 アルカリゲネス属に属する微生物の培養液、
菌体又は菌体処理物を用いることによりカルボン酸誘導
体（I）を高濃度に分解処理することができる。
(57) [Summary] [Object] The present invention decomposes a carboxylic acid derivative (I) using a culture solution, a microbial cell or a treated product of a microorganism having an ability to assimilate the carboxylic acid derivative (I). Provide a way to do. [Structure] The following formula (I): (In the formula, R 1 represents a hydrogen atom or an alkali metal atom,
R 2 and R 3 are the same or different and each represents a hydrogen atom or a methyl group, and X represents an amino group, a hydroxy group or a methoxy group. ) Degradation of a carboxylic acid derivative, characterized in that the carboxylic acid derivative represented by Law. [Effect] A culture solution of a microorganism belonging to the genus Alcaligenes,
The carboxylic acid derivative (I) can be decomposed to a high concentration by using the cells or the treated product of the cells.
Description
【０００１】[0001]
【産業上の利用分野】本発明は、次式（I）：The present invention has the following formula (I):
【０００２】[0002]
【化２】 Embedded image
【０００３】（式中、Ｒ1は水素原子又はアルカリ金属
原子を表し、Ｒ2及びＲ3は同一又は相異なり、水素原子
又はメチル基を表し、Ｘはアミノ基、ヒドロキシ基又は
メトキシ基を表す。）で示されるカルボン酸誘導体の微
生物分解法に関する。(Wherein R 1 represents a hydrogen atom or an alkali metal atom, R 2 and R 3 are the same or different and represent a hydrogen atom or a methyl group, and X represents an amino group, a hydroxy group or a methoxy group. The microbial decomposition method of the carboxylic acid derivative shown by.
【０００４】[0004]
【従来の技術】本発明に係わるカルボン酸誘導体（I）
は、下記の式に示すように、α，β−不飽和カルボン酸
誘導体（II）と亜硫酸又はそのアルカリ金属塩（III）
とが共存すると容易に生成する化合物である。2. Description of the Related Art Carboxylic acid derivatives (I) according to the present invention
Is an α, β-unsaturated carboxylic acid derivative (II) and sulfurous acid or its alkali metal salt (III) as shown in the following formula.
It is a compound that is easily formed when and coexist.
【０００５】[0005]
【化３】 Embedded image
【０００６】（式中、Ｒl、Ｒ2及びＲ3は前記と同義で
ある。） このカルボン酸誘導体（I）は、通常の化学的酸化処理
（例えば、過マンガン酸による酸化）では分解されにく
いので、排水中に存在する場合には分解除去が困難であ
る。(In the formula, R 1 , R 2 and R 3 have the same meanings as described above.) This carboxylic acid derivative (I) is decomposed by an ordinary chemical oxidation treatment (for example, oxidation with permanganate). Since it is difficult, it is difficult to decompose and remove it when it exists in the waste water.
【０００７】[0007]
【発明が解決しようとする課題】本発明は、微生物を利
用してカルボン酸誘導体（I）を分解する方法を提供す
ることを目的とする。An object of the present invention is to provide a method for decomposing a carboxylic acid derivative (I) using a microorganism.
【０００８】[0008]
【課題を解決するための手段】本発明者らは、前述した
目的を達成すべく、広く微生物の探索を行った結果、カ
ルボン酸誘導体（I）を資化する能力を有するアルカリ
ゲネス（Alcaligenes）属の微生物を用いることにより
該カルボン酸誘導体を分解処理できることを見い出し、
本発明に到達した。Means for Solving the Problems As a result of extensively searching for microorganisms in order to achieve the above-mentioned object, the present inventors have found that the genus Alcaligenes has the ability to assimilate carboxylic acid derivative (I). Found that the carboxylic acid derivative can be decomposed by using the microorganism of
The present invention has been reached.
【０００９】即ち、本発明は、次式（I）：That is, the present invention provides the following formula (I):
【００１０】[0010]
【化４】 Embedded image
【００１１】（式中、Ｒ1は水素原子又はアルカリ金属
原子を表し、Ｒ2及びＲ3は同一又は相異なり、水素原子
又はメチル基を表し、Ｘはアミノ基、ヒドロキシ基又は
メトキシ基を表す。）で示されるカルボン酸誘導体を、
アルカリゲネス属に属し、該カルボン酸誘導体を資化す
る能力を有する微生物の培養液、菌体又は菌体処理物で
処理することを特徴とするカルボン酸誘導体の分解法で
ある。(Wherein R 1 represents a hydrogen atom or an alkali metal atom, R 2 and R 3 are the same or different and represent a hydrogen atom or a methyl group, and X represents an amino group, a hydroxy group or a methoxy group. ), A carboxylic acid derivative represented by
A method for decomposing a carboxylic acid derivative, which comprises treating with a culture solution of a microorganism belonging to the genus Alcaligenes and having the ability to assimilate the carboxylic acid derivative, a microbial cell, or a treated product of the microbial cell.
【００１２】本発明に用いる微生物としては、アルカリ
ゲネス属に属し、且つカルボン酸誘導体（I）を資化す
る能力を有するものであれば、特に制限はない。The microorganism used in the present invention is not particularly limited as long as it belongs to the genus Alcaligenes and has the ability to assimilate the carboxylic acid derivative (I).
【００１３】かかる微生物の代表的なものとしては、ア
ルカリゲネスｓｐ．ＭＲ−２２０１株が挙げられる。Typical of such microorganisms are Alcaligenes sp. MR-2201 strain is mentioned.
【００１４】アルカリゲネスｓｐ．ＭＲ−２２０１株
は、本発明者らが新たに土壌中から分離したもので、通
商産業省工業技術院生命工学工業技術研究所にＦＥＲＭ
Ｐ−１３９５８として寄託されており、その菌学的性質
は以下に示す通りである。Alcaligenes sp. The MR-2201 strain was newly isolated from the soil by the present inventors, and has been confirmed by the FERM at the Institute of Biotechnology, Institute of Biotechnology, Ministry of International Trade and Industry.
It has been deposited as P-13958, and its mycological properties are as shown below.
【００１５】 形態 桿 菌 グラム染色性 − 胞子 − 運動性 ＋ 鞭毛 周 毛 酸素に対する態度 好気性 オキシダーゼ ＋ 力タラーゼ ＋ ＯＦテスト − キノン系 Ｑ−８ 以上の菌学的性質をBergey's Manual of Systematic Ba
cteriology(1986)に基づいて分類すると、アルカリゲネ
スｓｐ．ＭＲ−２２０１株はアルカリゲネス属に属する
細菌であると同定された。Morphological bacillus Gram stainability-spore-motility + flagella pericardium attitude toward oxygen aerobic oxidase + force thalase + OF test-quinone system Q-8
Based on cteriology (1986), Alcaligenes sp. The MR-2201 strain was identified as a bacterium belonging to the genus Alcaligenes.
【００ｌ６】前記微生物を用いてカルボン酸誘導体
（I）を処理するには、通常の培養で得られる培養液、
菌体又は菌体処理物（破砕菌体、粗・精製酵素、固定化
菌体・酵素等）を含む媒体中にカルボン酸誘導体（I）
を共存させることができるが、前述したアルカリゲネス
ｓｐ．ＭＲ−２２０１株のようにカルボン酸誘導体
（I）を唯一炭素源、窒素源として生育する微生物を用
いる場合は、特に他の炭素源や窒素源を加えなくても、
微生物を培養する過程でカルボン酸誘導体（I）を資化
せしめて処理することも可能である。To treat the carboxylic acid derivative (I) with the above-mentioned microorganism, a culture solution obtained by ordinary culture,
Carboxylic acid derivative (I) in a medium containing cells or treated cells (crushed cells, crude / purified enzyme, immobilized cells / enzyme, etc.)
Can be made to coexist, but the above-mentioned Alcaligenes sp. When a carboxylic acid derivative (I) such as the MR-2201 strain is used as a sole carbon source and a nitrogen source and a microorganism that grows is used, it is not necessary to add any other carbon source or nitrogen source.
It is also possible to assimilate the carboxylic acid derivative (I) and process it during the process of culturing the microorganism.
【００１７】例えば、カルボン酸誘導体（I）の代表的
化合物である次式（Ｉａ）：For example, the following formula (Ia), which is a typical compound of the carboxylic acid derivative (I):
【００１８】[0018]
【化５】 Embedded image
【００１９】で示されるアクリルアミドの亜硫酸付加体
（以下「化合物（Ｉａ）」という。）を唯一炭素源、窒
素源として用いた培地でアルカリゲネスｓｐ．ＭＲ−２
２０１株を培養することにより目的が達せられる。In a medium in which the sulfite adduct of acrylamide (hereinafter referred to as "compound (Ia)") represented by the formula (1) was used as the sole carbon source and nitrogen source, Alcaligenes sp. MR-2
The purpose can be achieved by culturing the 201 strain.
【００２０】又、次式（Ｉｂ）：Further, the following equation (Ib):
【００２１】[0021]
【化６】 [Chemical 6]
【００２２】で示されるアクリル酸の亜硫酸付加体（以
下「化合物（Ｉｂ）」という。）を唯一炭素源として用
い、任意の窒素源を添加した培地でアルカリゲネスＳ
ｐ．ＭＲ−２２０１株を培養することによっても目的を
達成することができる。Alkaligenes S in a medium in which a sulfite adduct of acrylic acid (hereinafter referred to as "compound (Ib)") represented by is used as the sole carbon source and an arbitrary nitrogen source is added.
p. The purpose can also be achieved by culturing the MR-2201 strain.
【００２３】本発明においては、この培養に際してはカ
ルボン酸誘導体（I）を０．５〜ｌ重量％含有する液体
培地にリン酸、マグネシウム等の無機塩類を共存させた
液体培地が好ましく用いられる。In the present invention, a liquid medium containing 0.5 to 1% by weight of the carboxylic acid derivative (I) in the presence of inorganic salts such as phosphoric acid and magnesium is preferably used in the present invention.
【００２４】なお、培養は通常１０〜４０℃、ｐＨ５〜
１０で好気的に行い、好ましくは３０℃前後、ｐＨ６〜
８で行う。培地のｐＨは水酸化ナトリウム等を用いて調
整するのが好ましい。The culture is usually carried out at 10 to 40 ° C. and pH 5 to 5.
Aerobic at 10, preferably around 30 ° C, pH 6-
Do in 8. The pH of the medium is preferably adjusted with sodium hydroxide or the like.
【００２５】[0025]
【実施例】以下、参考例及び実施例により本発明を更に
詳細に説明するが、これらは本発明の範囲を何等制限す
るものではない。The present invention will be described in more detail with reference to Reference Examples and Examples below, but these do not limit the scope of the present invention in any way.
【００２６】（参考例１）アクリルアミド亜硫酸付加体
（化合物（Ｉａ））の合成 蒸留水４００ｍｌに溶解させた亜硫酸水素ナトリウム２
５０ｇ中にアクリル酸１７Ｏｇを滴下、５時問攪津し
た。反応液から水を留去し、アセトン中に注ぎ入れるこ
とにより白色固体を生成させた。生成した固体を漉別、
取得した。更に、取得物をアセトンで十分に洗浄し、乾
燥させることにより化合物（Ｉａ）３００ｇを得た。取
得物が目的物（Ｉａ）であることをＩＲ、ＮＭＲで確認
した。Reference Example 1 Synthesis of Acrylamide Sulfite Adduct (Compound (Ia)) Sodium Bisulfite 2 dissolved in 400 ml of distilled water
17Og of acrylic acid was dripped into 50g and stirred at 5 o'clock. Water was distilled off from the reaction solution and poured into acetone to produce a white solid. Strain generated solid,
I got it. Further, the obtained material was thoroughly washed with acetone and dried to obtain 300 g of compound (Ia). It was confirmed by IR and NMR that the obtained product was the desired product (Ia).
【００２７】（参考例２）アクリル酸亜硫酸付加体（化
合物（Ｉｂ））の合成 蒸留水４００ｍｌに溶解させた亜硫酸水素ナトリウム２
５０ｇ中に、蒸留水２００ｍｌに溶解させたアクリル酸
１７０ｇを滴下、５時間攪枠した。反応液から水を留去
し、アセトン中に注ぎ入れることにより白色固体を生成
させた。生成した固体を楓別、取得した。更に、取得物
をアセトンで十分に洗浄し、乾燥させることにより化合
物（Ｉｂ）３２０ｇを得た。取得物が目的物（Ｉｂ）で
あることをＩＲ、ＮＭＲで確認した。Reference Example 2 Synthesis of Sulfuric Acid Sulfite Adduct (Compound (Ib)) Sodium Bisulfite 2 dissolved in 400 ml of distilled water
170 g of acrylic acid dissolved in 200 ml of distilled water was added dropwise to 50 g, and the mixture was stirred for 5 hours. Water was distilled off from the reaction solution and poured into acetone to produce a white solid. The generated solid was separated and collected. Further, the obtained material was thoroughly washed with acetone and dried to obtain 320 g of compound (Ib). It was confirmed by IR and NMR that the obtained product was the desired product (Ib).
【００２８】実施例１ 参考例１で合成した化合物（Ｉａ）ｌｇを含む表１に示
す培地１００ｍｌを５００ｍｌ容の坂ロフラスコに分注
し、１２１℃で２０分間加熱殺菌した。これにアルカリ
ゲネスｓｐ．ＭＲ−２２０１株を接種し、３０℃で振と
う培養を行った。菌体濃度の経時変化は波長６１０ｎｍ
の濁度を指標として求めた。培養液中の化合物（Ｉａ）
の濃度は高速液体クロマトグラフィー法で測定した。こ
の結果を図１に示す。この結果により、アルカリゲネス
ｓｐ．ＭＲ−２２０１株が経時的に化合物（Ｉａ）を分
解することを確認した。Example 1 100 ml of the medium shown in Table 1 containing 1 g of the compound (Ia) synthesized in Reference Example 1 was dispensed into a 500 ml Sakaro flask and sterilized by heating at 121 ° C. for 20 minutes. Alcaligenes sp. MR-2201 strain was inoculated and shake culture was performed at 30 ° C. Wavelength of cell concentration changes at 610 nm
The turbidity was calculated as an index. Compound (Ia) in culture solution
Was measured by high performance liquid chromatography. The result is shown in FIG. From this result, Alcaligenes sp. It was confirmed that the MR-2201 strain decomposes the compound (Ia) over time.
【００２９】[0029]
【表１】 [Table 1]
【００３０】実施例２ 参考例２で合成した化合物（Ｉｂ）ｌｇを含む表２に示
す培地１００ｍｌを５００ｍｌ容の坂ロフラスコに分注
し、１２１℃で２０分問加熱殺菌した。これにアルカリ
ゲネスＳｐ．ＭＲ−２２０１株を接種し、３０℃で振と
う培養を行った。菌体濃度の経時変化は波長６１０ｎｍ
の濁度を指標として求めた。培養液中の化合物（Ｉｂ）
の濃度は高速液体クロマトグラフィー法で測定した。４
８時間後の化合物（Ｉｂ）の分解率は９５％、菌体濃度
はＯＤ610の指標で１０．５に達した。この結果によ
り、アルカリゲネスＳｐ．ＭＲ−２２０１株が経時的に
化合物（Ｉｂ）を分解することを確認した。Example 2 100 ml of the medium shown in Table 2 containing 1 g of the compound (Ib) synthesized in Reference Example 2 was dispensed into a 500 ml Sakaro flask and heat-sterilized at 121 ° C. for 20 minutes. Alcaligenes Sp. MR-2201 strain was inoculated and shake culture was performed at 30 ° C. Wavelength of cell concentration changes at 610 nm
The turbidity was calculated as an index. Compound (Ib) in culture solution
Was measured by high performance liquid chromatography. Four
The decomposition rate of the compound (Ib) after 8 hours was 95%, and the bacterial cell concentration reached 10.5 as an index of OD 610 . From this result, Alcaligenes Sp. It was confirmed that the MR-2201 strain decomposes the compound (Ib) over time.
【００３１】[0031]
【表２】 [Table 2]
【００３２】[0032]
【発明の効果】本発明によれば、アルカリゲネス属に属
する微生物を用いることによリカルボン酸誘導体（I）
を分解処理できるという優れた効果を奏する。INDUSTRIAL APPLICABILITY According to the present invention, a carboxylic acid derivative (I) can be obtained by using a microorganism belonging to the genus Alcaligenes.
It has an excellent effect that can be decomposed.
【図ｌ】アルカリゲネスｓｐ．ＭＲ−２２０１株の培養
液中の化合物（Ｉａ）の濃度及び菌体濃度の経時変化加
を示す図である。FIG. 1 Alcaligenes sp. It is a figure which shows the time-dependent change of the density | concentration of a compound (Ia) in a culture solution of MR-2201 strain, and a bacterial cell density.
■：化合物（Ｉａ）の濃度 ○：菌体濃 ■: Concentration of compound (Ia) ○: Cell concentration
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 (Ｃ１２Ｐ 7/00 Ｃ１２Ｒ 1:05） ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Office reference number FI technical display location (C12P 7/00 C12R 1:05)
Claims (2)
Ｒ2及びＲ3は同一又は相異なり、水素原子又はメチル基
を表し、Ｘはアミノ基、ヒドロキシ基又はメトキシ基を
表す。）で示されるカルボン酸誘導体を、アルカリゲネ
ス属に属し、該カルボン酸誘導体を資化する能力を有す
る微生物の培養液、菌体又は菌体処理物で処理すること
を特徴とするカルボン酸誘導体の分解法。1. The following formula (I): (In the formula, R 1 represents a hydrogen atom or an alkali metal atom,
R 2 and R 3 are the same or different and each represents a hydrogen atom or a methyl group, and X represents an amino group, a hydroxy group or a methoxy group. ) Degradation of a carboxylic acid derivative, characterized in that the carboxylic acid derivative represented by Law.
０１株であることを特徴とする請求項１記載のカルボン
酸誘導体の分解法。2. The microorganism is Alcaligenes sp. MR-22
The method for decomposing a carboxylic acid derivative according to claim 1, which is strain 01.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15070995A JPH09276A (en) | 1995-06-16 | 1995-06-16 | Decomposition method for carboxylic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15070995A JPH09276A (en) | 1995-06-16 | 1995-06-16 | Decomposition method for carboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09276A true JPH09276A (en) | 1997-01-07 |
Family
ID=15502701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15070995A Pending JPH09276A (en) | 1995-06-16 | 1995-06-16 | Decomposition method for carboxylic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH09276A (en) |
-
1995
- 1995-06-16 JP JP15070995A patent/JPH09276A/en active Pending
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