JPS6371196A - Production of d-n-carbamyl-alpha-amino acid - Google Patents
Production of d-n-carbamyl-alpha-amino acidInfo
- Publication number
- JPS6371196A JPS6371196A JP21586586A JP21586586A JPS6371196A JP S6371196 A JPS6371196 A JP S6371196A JP 21586586 A JP21586586 A JP 21586586A JP 21586586 A JP21586586 A JP 21586586A JP S6371196 A JPS6371196 A JP S6371196A
- Authority
- JP
- Japan
- Prior art keywords
- carbamyl
- amino acid
- substituted
- microbial cells
- hansenula
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 3
- 150000001371 alpha-amino acids Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 244000005700 microbiome Species 0.000 abstract description 18
- 150000001469 hydantoins Chemical class 0.000 abstract description 13
- 241000235648 Pichia Species 0.000 abstract description 10
- 230000000813 microbial effect Effects 0.000 abstract description 6
- 241000320412 Ogataea angusta Species 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000012531 culture fluid Substances 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 229940091173 hydantoin Drugs 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000007650 D alpha amino acids Chemical class 0.000 description 2
- JDXMIYHOSFNZKO-BYPYZUCNSA-N N-carbamoyl-L-valine Chemical compound CC(C)[C@@H](C(O)=O)NC(N)=O JDXMIYHOSFNZKO-BYPYZUCNSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 description 1
- 229930182831 D-valine Natural products 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000007218 ym medium 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、５−置換ヒダントイン類をＤ−Ｎ−カルバミ
ル−α−アミノ酸に変換する能力を有するハンセニュラ
（Ｈａｎｓｅｎｕ ｌａ）属に属する微生物を用いるこ
とによりＤ−Ｎ−カルバミル−α−アミノ酸に変換する
方法に関し、医薬、農薬の中間原料を極めて有利に製造
することを目的とする。Detailed Description of the Invention (Industrial Application Field) The present invention uses a microorganism belonging to the genus Hansenula that has the ability to convert 5-substituted hydantoins into D-N-carbamyl-α-amino acids. The present invention relates to a method for converting into DN-carbamyl-α-amino acid, and aims to extremely advantageously produce intermediate raw materials for pharmaceuticals and agricultural chemicals.
（従来の技術とその問題点）
医薬、農薬の中間原料としては例えば、Ｄ−フェニルグ
リシン、 ｏ−ｐ−ヒドロヒシフェニルグリシンおよび
Ｄ−バリンなどがある。これらのＤ−α−アミノ酸は化
学合成によって得られるＤＬ体を光学分割して製造する
方法および本発明のように微生物を利用して５−置換ヒ
ダントイン類をＤ−Ｎ−カルバミル−α−アミノ酸類に
変換させる方法としては特開昭５３−９１１８９号が知
られている。(Prior art and its problems) Examples of intermediate raw materials for pharmaceuticals and agricultural chemicals include D-phenylglycine, op-hydrohycyphenylglycine, and D-valine. These D-α-amino acids can be produced by optically resolving DL forms obtained by chemical synthesis, and by using microorganisms as in the present invention to convert 5-substituted hydantoins into D-N-carbamyl-α-amino acids. Japanese Patent Laid-Open Publication No. 53-91189 is known as a method for converting into
本発明が解決しようとする問題点は従来のＤ−Ｎ−カル
バミル−α−アミノ酸の製造法よりも更に安価な良い製
造法を開発することにある。The problem to be solved by the present invention is to develop a method for producing D-N-carbamyl-α-amino acid that is cheaper and better than the conventional method.
（問題点を解決するための手段）
本発明者らはこの様な従来のＤ−Ｎ−カルバミルーα−
アミノ酸の製造に対してより効率の良い方法を見いだす
べく研究した結果、ハンセニュラ属に属する微生物が５
＝置換ヒダントインを水解してＤ−Ｎ−力シバミル−α
−アミノ酸に変換する能力を有する事を初めて見い出し
１本発明を完成するに至ったφ
即ち本発明は一般式（１）
％式％
（式中 Ｒはアルキル基、置換アルキル基、フェニル基
または置換フェニル基を示す）で表わされる５−置換ヒ
ダントイン類にハンセニュラ（Ｈａｎｓｅｎｕｌａ）属
に属する微生物の培養液、菌体または菌体処理物を作用
させてＤ−Ｎ−カルバミル−α−アミノ酸に変換させる
ことを特徴とする一般式（式中 Ｒは式（１）に同じ）
で表されるＤ−Ｎ−カルバミル−α−アミノ酸の製造方
法に関するものである。(Means for Solving the Problems) The present inventors have developed the conventional D-N-carbamyl α-
As a result of research to find a more efficient method for producing amino acids, five microorganisms belonging to the genus Hansenula were discovered.
= Substituted hydantoin is hydrolyzed to produce D-N-force-shibamyl-α
It was discovered for the first time that φ has the ability to convert into an amino acid, leading to the completion of the present invention. That is, the present invention is based on the general formula (1) % formula % (wherein R is an alkyl group, a substituted alkyl group, a phenyl group, or a substituted 5-substituted hydantoins (representing a phenyl group) are reacted with a culture solution, bacterial cells, or treated bacterial cells of a microorganism belonging to the genus Hansenula to convert them into D-N-carbamyl-α-amino acids. A general formula characterized by (in the formula, R is the same as formula (1))
The present invention relates to a method for producing DN-carbamyl-α-amino acid represented by:
また、光学活性のＮ−カルバミル−α−アミノ酸を亜硝
酸と反応させると、光学活性を保持したままのα−アミ
ノ酸が得られることは既に知られている。従って９本発
明の方法をこの方法と組合せることにより、Ｄ−α−ア
ミノ酸類を工業的に作ることができる。Furthermore, it is already known that when an optically active N-carbamyl-α-amino acid is reacted with nitrous acid, an α-amino acid that retains its optical activity can be obtained. Therefore, by combining the method of the present invention with this method, D-α-amino acids can be produced industrially.
本発明の目的のために使用されうる微生物は。Microorganisms that can be used for the purposes of the present invention are:
例えば代表例としては、ハンセニュラ シフェリ（Ｈａ
ｎｓｅｎｕｌａ ｃｉｆｅｒｒｉｉ）、ハンセニュラ
ヘンリソシー（Ｈａｎｓｅｎｕｌａ ｈｅｎｒｉｃｉｉ
）、ハンセニュラ ノフエルメンタス（Ｈａｎｓｅｎｕ
ｌａ ｎｏｎｆｅｒｍｅｎｔａｕｓ）、ハンセニュラ
ポリモルフｙ （Ｈａｎｓｅｎｕｌａ ｐｏｌｙｍｏｒ
ｐｈａ）などが挙げられ、これらは本発明の目的に使用
されうるかぎり自然界に存在する野生株および公的な微
生物保存機関に保存されている微生物が用いられる。For example, a representative example is Hansenula schiferi (Ha
nsenula ciferrii), Hansenula
Hansenula henricii
), Hansenula nofuermentus (Hansenu
la nonfermentaus), Hansenula
Polymorph y (Hansenula polymor
pha), and as long as they can be used for the purpose of the present invention, wild strains existing in nature and microorganisms preserved in public microorganism repositories are used.
本発明で用いられる５−置換ヒダントイン類とは。What are the 5-substituted hydantoins used in the present invention?
ヒタントインの５位の水素原子がアルキル基、フェニル
基またはそれらの置換誘導体でありアルキル基またはフ
ェニル基に付随する置換基としては。The hydrogen atom at position 5 of hytantoin is an alkyl group, a phenyl group, or a substituted derivative thereof, and the substituent attached to the alkyl group or phenyl group is.
例えばハロゲン原子、アルキルメルカプト基、ヒドロキ
シル基、アルコキシ基、アミノ基、インドリル基、アル
コキシカルボニル基などがある。Examples include a halogen atom, an alkylmercapto group, a hydroxyl group, an alkoxy group, an amino group, an indolyl group, and an alkoxycarbonyl group.
本機生物の培養に用いられる培地は通常資化しうる炭素
源、窒素源および微生物の生育に必要な無機栄養素を含
存させる通常の培地である。培養条件は好気的条件下に
てｐＨ３〜９．温度１５〜４０°Ｃの適当の範囲に制御
しつつ行えばよい。５−置換ヒダントインのＩ）−Ｎ−
カルバミル−α−アミノ酸に変換せしめる方法は前記の
微生物の培養液、菌体または菌体処理物の形態で使用で
きる。微生物の培養液をそのまま使用してよいが培養液
中の成分が障害になる場合や菌体量を多く使用したい場
合には、培養液から分離した菌体を用いればよい。The medium used for culturing this organism is a normal medium containing an assimilable carbon source, a nitrogen source, and inorganic nutrients necessary for the growth of microorganisms. The culture conditions are aerobic and pH 3 to 9. It may be carried out while controlling the temperature within an appropriate range of 15 to 40°C. I)-N- of 5-substituted hydantoins
The method for converting into carbamyl-α-amino acid can be used in the form of a culture solution, bacterial cells, or processed bacterial cells of the above-mentioned microorganisms. The culture solution of the microorganism may be used as it is, but if components in the culture solution become a hindrance or if a large amount of microorganisms are desired to be used, microbial cells separated from the culture solution may be used.
反応基質である５−置換ヒダントインに微生物の培養液
、菌体または菌体処理物を作用させるにはｉｍ常、水性
媒体中で行う方法が用いられ１反応基質の濃度は０．１
〜１０重量％の濃度で用いられる。A method is usually used in which a microorganism culture solution, bacterial cells, or treated bacterial cells are allowed to act on 5-substituted hydantoin, which is a reaction substrate, in an aqueous medium, and the concentration of one reaction substrate is 0.1.
Used at a concentration of ~10% by weight.
また反応における温度およびｐ）ｌは使用する微生物の
５−置換ヒダントインをＤ−Ｎ−力シバミル−α−アミ
ノ酸へ変換する能力を持つ酵素の至適温度および至適ｐ
ｉ（が採用されるが通常、温度は１５〜６０℃。In addition, the temperature and p)l in the reaction are the optimal temperature and p) of the microorganism used, which has the ability to convert 5-substituted hydantoin into D-N-sivamyl-α-amino acid.
i( is adopted, but the temperature is usually 15 to 60°C.
ｐＨは９〜１１の範囲である。反応？８液中のｐＨは反
応の進行に伴って低下するので適時中和剤を添加して前
記の至適ｐＨに保持することが望ましい。中和剤として
は苛性ソーダ、苛性カリ、アンモニア。The pH ranges from 9 to 11. reaction? Since the pH of the 8 liquid decreases as the reaction progresses, it is desirable to add a neutralizing agent from time to time to maintain it at the optimum pH. Neutralizing agents include caustic soda, caustic potash, and ammonia.
炭酸ソーダなどが適当である。このようにして得られた
Ｄ−Ｎ−カルバミル−α−アミノ酸を反応溶液中からの
分離にはイオン交換樹脂などを用いる通常の方法が採用
できる。生成したＤ−Ｎ−力シバミル−α−アミノ酸の
定量はｐ−ジメチルアミノベンズアルデハイドを用いる
比色法および）夜体クロマトグラフィで測定する方法を
用いた。光学異性体は結晶の比旋光度の測定および光学
分割カラム（キラルパソクＷＨ・・・ダイセル社製）を
用いる液体クロマトによってり、Ｌを確認した。Carbonated soda etc. are suitable. The D-N-carbamyl-α-amino acid thus obtained can be separated from the reaction solution by a conventional method using an ion exchange resin or the like. The produced D-N-sibamyl-α-amino acid was determined by a colorimetric method using p-dimethylaminobenzaldehyde and by night chromatography. The optical isomer was confirmed to be L by measuring the specific optical rotation of the crystal and liquid chromatography using an optical resolution column (Chiral Pasok WH, manufactured by Daicel Corporation).
（発明の作用および効果）
本発明によれば、微生物を用いることにより５−置換ヒ
ダントインから容易に高収率でＤ−Ｎ−カルバミル−α
−アミノ酸を取得することができる。即ち１本発明にお
いてはハンセニュラ属に属する微生物を用いて５−置換
ヒダントインから効率よ＜０−Ｎ−カルバミル−α−ア
ミノ酸に変換することが出来、 Ｄ−Ｎ−カルバミル−
α−アミノ酸の製造方法としては極めて有利な方法であ
る。(Operations and Effects of the Invention) According to the present invention, D-N-carbamyl-α can be easily obtained in high yield from 5-substituted hydantoin by using microorganisms.
- Amino acids can be obtained. That is, in the present invention, 5-substituted hydantoin can be efficiently converted to <0-N-carbamyl-α-amino acid using a microorganism belonging to the genus Hansenula, and D-N-carbamyl-
This is an extremely advantageous method for producing α-amino acids.
（実施例） 以下の例により本発明を具体的に説明する。(Example) The invention will be specifically explained by the following examples.
実施例−１
グルコース２０ＩＦｆ！、 ＤＬ−５−フェニルヒダン
トイン５脅、マルタエキス１脅、酵母エキス３１９．Ｋ
Ｈ２ＰＯ４１，５’Ｆｆｌ１ＭｇＳＯａ４ＨｔＯＯ，５
脅、 ＣａＣ１ｚ・２Ｈｚ００．３３す（ｐＨ６）の培
地を２５０−三角フラスコに２０ｍ１ｉ入れ１２０℃、
１５分間殺菌した。Example-1 Glucose 20IFf! , 5 parts of DL-5-phenylhydantoin, 1 part of Maltese extract, 319 parts of yeast extract. K
H2PO41,5'Ffl1MgSOa4HtOO,5
Pour 20ml of a medium containing CaC1z/2Hz00.33S (pH 6) into a 250-Erlenmeyer flask and heat at 120°C.
Sterilized for 15 minutes.
これに酵母ＹＭ培地で２８℃、２４時間培養したハンセ
ニュラ ポリモルファ（ＮＲＲＬ Ｙ〜２４２３）を１
白金耳接種し、２８℃２４時間培養した。この培養液を
遠心分離により菌体を採取し、培養液と同量の殺菌した
生理食塩水にて１回洗浄し菌体を集めた。To this, 1 portion of Hansenula polymorpha (NRRL Y~2423) cultured in yeast YM medium at 28°C for 24 hours was added.
A platinum loop was inoculated and cultured at 28°C for 24 hours. Bacterial cells were collected by centrifugation of this culture solution, and washed once with sterilized physiological saline in the same amount as the culture solution to collect the microbial cells.
この菌体を０Ｌ−５−イソプロピルヒダントイン１０今
を含む０．１Ｍ）リスハ”ソファ（ｐＨ９，０）・・・
終末５ｄ・・・に３０９になる様に添加し３２℃で２４
時間反応した。This bacterial cell was added to 0.1M containing 0L-5-isopropylhydantoin (pH 9,0)...
Terminal 5d... was added to 309 and heated to 24 at 32℃.
Time reacted.
生成したＮ−カルバミルバリンを前述の比色法で測定し
、 ５．２ ｍｇ／ｍｌの生成量を認め、またＮ−カル
バミルバリンを分離精製し旋光度を測定した結果。The produced N-carbamylvaline was measured by the colorimetric method described above, and the production amount was found to be 5.2 mg/ml, and the N-carbamylvaline was separated and purified and its optical rotation was measured.
０体であって〔α〕。ｔ５は−１４，１（Ｃ＝２．６１
Ｎ−ＮＨ，ＯＨ）を認めた。There are 0 bodies [α]. t5 is -14,1 (C=2.61
N-NH,OH) was observed.
＝５＝置換ヒダントインを反応させた結果を表−１に示
した。また生成した各種のＮ−カルバミル−α−アミノ
酸は光学分割カラムによる光学活性測定により、全ての
場合り体であった。The results of reacting the =5=substituted hydantoin are shown in Table 1. Furthermore, the various N-carbamyl-α-amino acids produced were all in the form of solid forms when optical activity was measured using an optical resolution column.
実施例−３
表−２に示す各種微生物を実施例−１と同様に調整して
得られた凹体を、 ０Ｌ−５−イソプロピルヒダントイ
ン１０脅を含む０．１Ｍ）リスバッファ（ｐＨ９゜０）
・・・終末５−・・・に３０句になるように添加し、３
２°Ｃ２２４時間反応した。Example 3 The concave bodies obtained by preparing the various microorganisms shown in Table 2 in the same manner as in Example 1 were added to 0.1 M) lithium buffer (pH 9°0) containing 0L-5-isopropylhydantoin 10%.
...Add to the ending 5-... so that there are 30 verses, 3
The reaction was carried out at 2°C for 224 hours.
生成したＮ−カルバミル−α−アミノ酸は前記の方法に
て測定した。また光学分割カラムによる光学活性測定に
より生成Ｎ−カルバミル−α−アミノ酸は全て０体であ
った。The produced N-carbamyl-α-amino acid was measured by the method described above. Furthermore, optical activity measurement using an optical resolution column revealed that all N-carbamyl-α-amino acids produced were 0.
Claims (1)
置換フェニル基）で表わされる５−置換ヒダントイン類
にハンセニュラ（Ｈａｎｓｅｎｕｌａ）属に属する微生
物の培養液、菌体または菌体処理物を作用させてＤ−Ｎ
−カルバミル−α−アミノ酸に変換させることを特徴と
する一般式（II） ▲数式、化学式、表等があります▼（II） （式中Ｒは前記に同じ）で表わされるＤ−Ｎ−カルバミ
ル−α−アミノ酸の製造方法[Claims] General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R is an alkyl group, a substituted alkyl group, a phenyl group,
D-N
General formula (II) characterized by conversion to -carbamyl-α-amino acid ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) D-N-carbamyl- represented by (in the formula, R is the same as above) Method for producing α-amino acids
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21586586A JPH0683677B2 (en) | 1986-09-16 | 1986-09-16 | Method for producing DN-carbamyl-α-amino acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21586586A JPH0683677B2 (en) | 1986-09-16 | 1986-09-16 | Method for producing DN-carbamyl-α-amino acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6371196A true JPS6371196A (en) | 1988-03-31 |
| JPH0683677B2 JPH0683677B2 (en) | 1994-10-26 |
Family
ID=16679551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21586586A Expired - Lifetime JPH0683677B2 (en) | 1986-09-16 | 1986-09-16 | Method for producing DN-carbamyl-α-amino acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0683677B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002022844A1 (en) * | 2000-09-18 | 2002-03-21 | Kaneka Corporation | Optically active fluorophenylalanine derivative and process for producing the same |
-
1986
- 1986-09-16 JP JP21586586A patent/JPH0683677B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002022844A1 (en) * | 2000-09-18 | 2002-03-21 | Kaneka Corporation | Optically active fluorophenylalanine derivative and process for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0683677B2 (en) | 1994-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2283376A1 (en) | Synthesis of optically active phenylalanine analogs through microbial transformations | |
| JPS61212292A (en) | Production of d-alpha-amino acid | |
| JPH0239B2 (en) | ||
| JP2840722B2 (en) | Method for producing 4-halo-3-hydroxybutyronitrile | |
| JPH0856659A (en) | Ribitol dehydrogenase and its production and use | |
| JPS6371196A (en) | Production of d-n-carbamyl-alpha-amino acid | |
| JP2696127B2 (en) | Method for producing optically active 2-hydroxycarboxylic acid | |
| JPS6310752A (en) | Production of trans-4-cyanocyclohexane-1-carboxylic acid | |
| JP3006615B2 (en) | Method for producing D-β-hydroxy amino acid | |
| JPS62111692A (en) | Production of d-alpha-amino acid | |
| JPH02104295A (en) | Production of optically active amine and its derivative | |
| JP2840723B2 (en) | Method for producing 4-halo-3-hydroxybutyronitrile | |
| JPS63112990A (en) | Production of d-alpha-amino acid | |
| JPS63148992A (en) | Production of fluorine-containing phenylalanine derivative from fluorine-containing cinnamic acid | |
| JPS5816692A (en) | Preparation of l-tryptophan by enzyme | |
| JP2866660B2 (en) | Method for producing N-carbamoyl-D-phenylglycine | |
| JPH0380476B2 (en) | ||
| JPH0588118B2 (en) | ||
| JPS63173595A (en) | Production of d-alpha-amino acid | |
| JPH0424992B2 (en) | ||
| JPS6324895A (en) | Production of l-amino acid or n-carbamyl-l-amino acid | |
| JPH01124398A (en) | Production of optically active hydantoins | |
| JPH0258280B2 (en) | ||
| JPS61152291A (en) | Production of d-n-carbamyl-alpha-aminoacid | |
| JPH01181797A (en) | Method for producing D-threo-3-(3,4-dihydroxyphenyl)serine derivative |