JPH01252295A - Production of 2,3-dicyano-5,6-dicyanopurazine - Google Patents
Production of 2,3-dicyano-5,6-dicyanopurazineInfo
- Publication number
- JPH01252295A JPH01252295A JP7590988A JP7590988A JPH01252295A JP H01252295 A JPH01252295 A JP H01252295A JP 7590988 A JP7590988 A JP 7590988A JP 7590988 A JP7590988 A JP 7590988A JP H01252295 A JPH01252295 A JP H01252295A
- Authority
- JP
- Japan
- Prior art keywords
- damn
- present
- trichoderma
- cultured
- medium containing
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 241000223259 Trichoderma Species 0.000 claims abstract description 6
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 claims abstract description 4
- 241000894006 Bacteria Species 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 8
- 241000223261 Trichoderma viride Species 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000012258 culturing Methods 0.000 abstract description 2
- 239000000835 fiber Substances 0.000 abstract description 2
- 241000233866 Fungi Species 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 15
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000918585 Pythium aphanidermatum Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 150000003216 pyrazines Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- FTHBTDDIVWLRLP-UHFFFAOYSA-N 5,6-diaminopyrazine-2,3-dicarbonitrile Chemical compound NC1=NC(C#N)=C(C#N)N=C1N FTHBTDDIVWLRLP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 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
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 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
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- JUFLTGRGLUCRCU-UHFFFAOYSA-N ethanediimidoyl dicyanide Chemical compound N#CC(=N)C(=N)C#N JUFLTGRGLUCRCU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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〕
本発明は微生物変換を利用したジアミノマレオニトリル
からの２．３−ジアミノ−５，６−ジシアノピラジン（
以下本ピラジンという）の製造方法に関するものである
。Detailed Description of the Invention [Industrial Application Field] The present invention is directed to the production of 2,3-diamino-5,6-dicyanopyrazine (
The present invention relates to a method for producing pyrazine (hereinafter referred to as the present pyrazine).
不発１〜ピラジンは、有用な合成中間体でありまた強い
蛍光性を有し繊維の増白剤として用いられる。Pyrazines are useful synthetic intermediates and have strong fluorescence and are used as fiber brighteners.
ジアミノマレオニトリル（以下ＤＡＭＮという）は、青
酸の４量体であり、多くの含窒素化合物の合成原料とし
て利用されている。本ピラジンの合成法として、ＤＡＭ
Ｎとオギザリルクロリドとの縮合体を塩素化したのちア
ンモニアと反応させる方法（成跋大学工学部報告 ２６
巻、１８６７頁）とＤＡＭＮをジクロルジシアノキノン
で酸化して得たジイミノサクシノニトリルとＤＡＭＮと
の縮合による方法（Ｊ、 Ｏｒｇ、 Ｃｈｅｍ、、 ３
９巻、１２３５頁）が知られている。Diaminomaleonitrile (hereinafter referred to as DAMN) is a tetramer of hydrocyanic acid, and is used as a raw material for the synthesis of many nitrogen-containing compounds. As a method for synthesizing this pyrazine, DAM
A method of chlorinating a condensate of N and oxalyl chloride and then reacting it with ammonia (Report of the Faculty of Engineering, Chengba University 26)
Vol., p. 1867) and a method by condensation of DAMN with diiminosuccinonitrile obtained by oxidizing DAMN with dichlorodicyanoquinone (J, Org, Chem, 3
Volume 9, page 1235) is known.
［発明の解決しようとする問題点］
これらの合成化学的方法は、いずれも工程が複雑で長く
、その上、総合収拾率も低く、工業的製造法として採用
するには適当でなかった。[Problems to be Solved by the Invention] All of these synthetic chemical methods involve complicated and long steps, and furthermore, have low overall yields, and are not suitable for use as industrial production methods.
本発明は、微生物を活用し、ＤＡＭＮから一挙に目的物
を得る方法釦春力である。The present invention is a method for obtaining a target product from DAMN all at once by utilizing microorganisms.
本発明は、トリコデルマ属に属する菌をＤＡＭＮを含有
む培地で培養し、培養物から本ピラジンを採取する方法
である。The present invention is a method for culturing a bacterium belonging to the genus Trichoderma in a medium containing DAMN, and collecting the present pyrazine from the culture.
ＤＡＭＮ 本ピラジン
本発明に使用される菌はトリコデルマ属、なかんずくト
リコデルマビリデが最も有効であり、イネ苗立枯れ病原
菌として公知であり、イネ苗から容易に分離することが
でき、又、財団法人醗酵研究所からＩＦｏ ３０４９８
として分譲を受けることができる。DAMN Present Pyrazine The most effective bacteria used in the present invention are Trichoderma genus, especially Trichoderma viride, which is known as a rice seedling damping-off pathogen and can be easily isolated from rice seedlings. IFo 30498 from the Institute
can be distributed as such.
本発明の培養は、炭素源、窒素源、無機塩、ビタミン類
などを含む通常の水溶液の培地中で行うな１し
ことができＤＡＭＮは５０ｐ＞％以上で存在させる。５
０ｐｐｍ以下では経済的に不利であり又、１％以上とな
ると、菌の生育が容易でなくなる。The culture of the present invention can be carried out in a conventional aqueous medium containing a carbon source, a nitrogen source, inorganic salts, vitamins, etc., and DAMN is present in an amount of 50 p>% or more. 5
If it is less than 0 ppm, it is economically disadvantageous, and if it is more than 1%, it becomes difficult for bacteria to grow.
、゛ 噌要禾ｔ０日―炭素源としては、
グルコース、しょ糖、デンプン等の糖類、グリセロール
等の多価アルコール、有機酸などが使用できる。窒素源
としてはアンモニウム塩、硝酸塩、アミノ酸などが使用
できる。その他の成分として金属塩、リン酸塩など必要
に応して培地に添加する。基質や生成物の微生物体内へ
の透過性を向上させるための試剤、例えば界面活性剤等
を加えてもよい。酵母エキス、肉エキス、ポテト煮出液
などを含む天然培地或は半合成培地を用いることもでき
る。, ゛ As for the carbon source,
Sugars such as glucose, sucrose and starch, polyhydric alcohols such as glycerol, organic acids, etc. can be used. Ammonium salts, nitrates, amino acids, etc. can be used as nitrogen sources. Other components such as metal salts and phosphates are added to the medium as necessary. Reagents, such as surfactants, may be added to improve the permeability of substrates and products into microorganisms. Natural or semi-synthetic media containing yeast extract, meat extract, potato broth, etc. can also be used.
本発明の培養は振盪または通気して行うのが好ましく、
温度は２０〜３０°Ｃで、ｐｌ＋は３〜６の間る。The culture of the present invention is preferably carried out with shaking or aeration.
The temperature is 20-30°C and the pl+ is between 3-6.
培養物より本ピラジンを取得するには、通常の方法に従
えばよい。例えば、培養液から遠心分離等によって菌体
を除去したのち、目的物を有機溶媒を用いて抽出し、カ
ラムクロマト等による分離精製に供して容易に結晶とし
て得ることができる。The present pyrazine can be obtained from a culture by following a conventional method. For example, after removing bacterial cells from the culture solution by centrifugation or the like, the target product can be extracted using an organic solvent and subjected to separation and purification using column chromatography or the like to easily obtain it as crystals.
得られた化合物は、標品と赤外吸収ベクトル、紫外吸収
スペクトル、薄層クロマトグラムなどを比較することに
より構造が一致することを確認できる。It can be confirmed that the structure of the obtained compound matches that of the standard product by comparing the infrared absorption vector, ultraviolet absorption spectrum, thin layer chromatogram, etc.
（発明の効果〕
本発明によれば複雑な工程を経ずに原料から一挙に複素
環化合物を合成できることになり、操作上の簡便化によ
る経済的効果が得られる。(Effects of the Invention) According to the present invention, a heterocyclic compound can be synthesized from raw materials all at once without going through complicated steps, and economical effects can be obtained due to operational simplification.
以下、実施例によって本発明をさらに具体的に説明する
。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
イネ苗立ち枯れ癩病原菌トリコデルマビリデをＤＡＭＮ
２０ ｐｐｍを含むポテトシュクロース寒天平板培地
〔佐藤昭二ら編「植物病理学実験法Ｊ（昭和５８年講談
社発行）１２頁参照〕に接種し２８°Ｃで２日間前培養
した。グリセロール１．０％、酵母エキス０．１％、硫
酸マグネシウム０．０５％、リン酸−カリウム０．２％
およびＤ Ａ Ｍ Ｎｏ、０５％を含む液体培地１２０
ｍ１に前培養した菌の一部を接種し、２８゛Ｃで７日間
振盪培養した。Example 1 Rice seedling damping-off leprosy pathogen Trichoderma viride was introduced into DAMN.
Potato sucrose agar plate medium containing 20 ppm [see "Plant Pathology Experimental Methods J (published by Kodansha, 1980), edited by Shoji Sato et al.], p. 12] was inoculated and precultured at 28°C for 2 days. Glycerol 1.0 %, yeast extract 0.1%, magnesium sulfate 0.05%, potassium phosphate 0.2%
and DA M No. 05% liquid medium 120
A part of the pre-cultured bacteria was inoculated into m1, and cultured with shaking at 28°C for 7 days.
菌体を濾別し、濾液を酢酸エチルで抽出した。The bacterial cells were filtered off, and the filtrate was extracted with ethyl acetate.
抽出物をシリカゲルカラムクロマトグラフィー（酢酸エ
チル／ｎ−ヘキサン−１／３で展開）により精製し白色
結晶として本ピラジン８．９ ｍｇを得た。The extract was purified by silica gel column chromatography (developed with ethyl acetate/n-hexane-1/3) to obtain 8.9 mg of the present pyrazine as white crystals.
（２分子のＤＡＭＮから１分子が生成するとして収率２
０％）
実施例２
上記実施例１と同様にトリコデルマ属の異なる菌株トリ
コデルマビリデ（ＩＦｏ ３０４９８）を用いて反応さ
せ本ピラジン６、６ ｍｇを得た。（収率１５χ）実施
例３
前記実施例１と同様の操作を行い、液体培養の前記培地
にさらにアスパラギン０．０１％、硫酸亜鉛０．０５％
の成分を加え、２８°Ｃで６日間振盪培養した。(Assuming that one molecule is produced from two molecules of DAMN, the yield is 2
0%) Example 2 In the same manner as in Example 1 above, a reaction was carried out using a different strain of Trichoderma genus Trichoderma viride (IFo 30498) to obtain 6.6 mg of the present pyrazine. (Yield 15χ) Example 3 The same operation as in Example 1 was carried out, and 0.01% asparagine and 0.05% zinc sulfate were added to the liquid culture medium.
Components were added and cultured with shaking at 28°C for 6 days.
Claims (1)
含む培地で培養し、培養物から２，３−ジアミノ−５，
６−ジシアノピラジンを採取することを特徴とする２，
３−ジアミノ−５，６−ジシアノピラジンの製造方法。Bacteria belonging to the genus Trichoderma are cultured in a medium containing diaminomaleonitrile, and 2,3-diamino-5,
2, characterized by collecting 6-dicyanopyrazine;
Method for producing 3-diamino-5,6-dicyanopyrazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7590988A JPH01252295A (en) | 1988-03-31 | 1988-03-31 | Production of 2,3-dicyano-5,6-dicyanopurazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7590988A JPH01252295A (en) | 1988-03-31 | 1988-03-31 | Production of 2,3-dicyano-5,6-dicyanopurazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01252295A true JPH01252295A (en) | 1989-10-06 |
Family
ID=13589936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7590988A Pending JPH01252295A (en) | 1988-03-31 | 1988-03-31 | Production of 2,3-dicyano-5,6-dicyanopurazine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01252295A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10399960B2 (en) | 2015-11-10 | 2019-09-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| CN113956207A (en) * | 2021-10-29 | 2022-01-21 | 中北大学 | Preparation method of 2,3,5, 6-pyrazine tetranitrile |
-
1988
- 1988-03-31 JP JP7590988A patent/JPH01252295A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10399960B2 (en) | 2015-11-10 | 2019-09-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10497878B2 (en) | 2015-11-10 | 2019-12-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10522763B2 (en) | 2015-11-10 | 2019-12-31 | Kyushu University, National Universit Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| CN113956207A (en) * | 2021-10-29 | 2022-01-21 | 中北大学 | Preparation method of 2,3,5, 6-pyrazine tetranitrile |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2676568B2 (en) | Method for producing R (-)-mandelic acid and its derivatives | |
| JP4858676B2 (en) | Process for producing L-threo-3,4-dihydroxyphenylserine | |
| JPH01252295A (en) | Production of 2,3-dicyano-5,6-dicyanopurazine | |
| JPH01168292A (en) | Production of d-glyceric acid | |
| JPS5923794B2 (en) | Manufacturing method of dihydroxyacetone | |
| JPS6310752A (en) | Production of trans-4-cyanocyclohexane-1-carboxylic acid | |
| US3975235A (en) | Process for the production of cephamycin type antibiotic substances | |
| JP2721536B2 (en) | Method for obtaining D-β-hydroxy amino acid | |
| JPH0473999B2 (en) | ||
| FR2557455A1 (en) | ANTIBIOTIC NEW 81-484 ANTITUMER AND ITS PRODUCTION | |
| JP3006615B2 (en) | Method for producing D-β-hydroxy amino acid | |
| JPH0740951B2 (en) | Method for producing hydroxide of nitrogen-containing heterocyclic compound by microorganism | |
| JPS6054303B2 (en) | Polyprenylsulfone derivative and method for producing the same | |
| JPS5953838B2 (en) | Method for producing β-hydroxyvaleric acid | |
| JP2631867B2 (en) | Method for producing (R) -2-hydroxy-4-phenyl-3-butenoic acid | |
| JPH02104295A (en) | Production of optically active amine and its derivative | |
| JPH0728750B2 (en) | Method for producing hydroxide of pyrazinic acid by microorganism | |
| JP2519980B2 (en) | Method for producing (S) -2-hydroxy-4-phenyl-3-butenoic acid | |
| JPS6219098A (en) | Separation of d-isomer from dl mixture of serine | |
| JPH10234363A (en) | New enzyme and production of para-hydroxybenzaldehyde derivative, etc., using the same | |
| JPS6312291A (en) | Production of trans-4-cyanocyclohexane-1-carboxylic acid | |
| JPS6283894A (en) | Production of coenzyme q11 | |
| JPS61285993A (en) | Production of phenacyl alcohol | |
| JPH07213295A (en) | Method for producing 4-hydroxy-2-methylbenzoic acid with microorganism | |
| JPH0123473B2 (en) |