JPH03280891A - Production of nicotinamide with microorganism - Google Patents
Production of nicotinamide with microorganismInfo
- Publication number
- JPH03280891A JPH03280891A JP8069790A JP8069790A JPH03280891A JP H03280891 A JPH03280891 A JP H03280891A JP 8069790 A JP8069790 A JP 8069790A JP 8069790 A JP8069790 A JP 8069790A JP H03280891 A JPH03280891 A JP H03280891A
- Authority
- JP
- Japan
- Prior art keywords
- microorganism
- reaction
- cyanopyridine
- nicotinic acid
- acid amide
- 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
- 244000005700 microbiome Species 0.000 title claims abstract description 25
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 39
- 235000005152 nicotinamide Nutrition 0.000 title claims description 19
- 239000011570 nicotinamide Substances 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 229960003966 nicotinamide Drugs 0.000 title description 4
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 241000186321 Cellulomonas Species 0.000 claims abstract description 6
- 241000187747 Streptomyces Species 0.000 claims abstract description 4
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- 238000006703 hydration reaction Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 239000000758 substrate Substances 0.000 abstract description 6
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 abstract description 3
- 241000187392 Streptomyces griseus Species 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 229930003270 Vitamin B Natural products 0.000 abstract description 2
- 235000019156 vitamin B Nutrition 0.000 abstract description 2
- 239000011720 vitamin B Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000000887 hydrating effect Effects 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 description 11
- -1 nitrile compound Chemical class 0.000 description 5
- 238000012258 culturing Methods 0.000 description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 4
- 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 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 241000186320 Cellulomonas fimi Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 229940047889 isobutyramide Drugs 0.000 description 2
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
- 239000008057 potassium phosphate buffer Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- 241000186146 Brevibacterium Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910021654 trace metal Inorganic materials 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
- 239000011782 vitamin Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野]
本発明は微生物によるニコチン酸アミドの製造法に関す
る。より詳しくは、3−シアノピリジンを特定の属の微
生物の作用による水和反応に付し、生成するニコチン酸
アミドを分離取得する微生物によるニコチン酸アミドの
製造法に関する。ニコチン酸アミドは水溶性ビタミンB
群の一種であり、補酵素の構成要素となっていることが
知られている。また、ニコチン酸アミド誘導体は医薬品
等に用いられている。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing nicotinamide using microorganisms. More specifically, the present invention relates to a method for producing nicotinic acid amide using a microorganism, in which 3-cyanopyridine is subjected to a hydration reaction by the action of a specific genus of microorganism, and the resulting nicotinic acid amide is separated and obtained. Nicotinamide is a water-soluble vitamin B
It is one of the group and is known to be a component of coenzymes. Furthermore, nicotinic acid amide derivatives are used in pharmaceuticals and the like.
従来、ニコチン酸アミドの製造法としては、βピコリン
のアンモ酸化により得られる3−シアノピリジンを還元
銅触媒を用いて接触水和する化学的合成法(特公昭48
−22710号、特開昭50−111077号各公報参
照)が知られいる。Conventionally, the method for producing nicotinamide has been a chemical synthesis method in which 3-cyanopyridine obtained by ammoxidation of β-picoline is catalytically hydrated using a reduced copper catalyst.
-22710 and Japanese Unexamined Patent Publication No. 50-111077) are known.
しかしながら、この方法は副成物の生成や精製工程が複
雑になるなどの問題があり、さらに新規で工業的に有利
な製造方法の開発が望まれていた。However, this method has problems such as the production of by-products and a complicated purification process, and there has been a desire to develop a new and industrially advantageous manufacturing method.
一方、ニトリルを水和する活性を有する微生物の作用に
より、3−シアノピリジンをニコチン酸アミドに変換す
る方法として、ブレビバクテリウム属の微生物を用いる
方法(特公昭62−21519号公報参照)、ロドコン
カス属ロドクロウス種の微生物を用いる方法(特開平2
−470号公報、Appl、 Enν1ron、 Mi
crobiol、 541766−1769 (198
8)参照)などが知られている。これらの微生物を用い
た製法は、化学的製法に比較して、穏和な条件下で反応
でき、反応副成物が少ないことから、より工業的に有利
な製法と考えられる。しかしながら、これら微生物につ
いては極めて多量の菌体を用いてニコチン酸アミドの生
成を行った実験例であったり、基礎的な実験がなされて
いるのみであったりして、工業化を目的とした検討にま
では至っていない。On the other hand, methods using microorganisms of the genus Brevibacterium (see Japanese Patent Publication No. 62-21519), Rhodoconcus Method using microorganisms of the genus Rhodoculus
-470 Publication, Appl, Enν1ron, Mi
crobiol, 541766-1769 (198
8)) are known. The production method using these microorganisms is considered to be a more industrially advantageous production method than chemical production methods because it can react under mild conditions and produces fewer reaction by-products. However, with regard to these microorganisms, there are examples of experiments in which nicotinic acid amide was produced using extremely large numbers of bacterial cells, and there are only basic experiments that have been conducted on these microorganisms. It has not yet been reached.
本発明者らは工業的生産を目的として、さらに有効な新
規微生物の探索を鋭意行った結果、分譲菌株中よりセル
ロモナス(Cel lulomonas)属またはスト
レプトマイセス(Streptomyces) IIE
に属する微生物に高い3−シアノピリジン水和活性を有
するものを見出し本発明を完成するに至った。The present inventors have diligently searched for new and more effective microorganisms for the purpose of industrial production, and as a result, among the strains provided, we found that the genus Cellulomonas or Streptomyces IIE
The present invention was completed by discovering a microorganism belonging to the genus that has high 3-cyanopyridine hydration activity.
すなわち、本発明は、3−シアノピリジンを微生物の作
用による水和反応によりニコチン酸アミドに変換するニ
コチン酸アミドの製造法において、該微生物として、セ
ルロモナス(Cellulo+l1onas)属または
ストレプトマイセス(Streptomyces)属に
属し該ニトリルを水和する能力を有する微生物を用いる
こと、を特徴とする微生物によるニコチン酸アミドの製
造法である。That is, the present invention provides a method for producing nicotinic acid amide in which 3-cyanopyridine is converted into nicotinic acid amide by a hydration reaction caused by the action of a microorganism, in which the microorganism is of the genus Cellulo+l1onas or the genus Streptomyces. This is a method for producing nicotinic acid amide using a microorganism, which is characterized by using a microorganism belonging to the nitrile group and having the ability to hydrate the nitrile.
本発明に用いる微生物としては、例えば、ストレプトマ
イセス グリセウス(Streptomyces gr
iseus) IFo 3355、セルロモナス フィ
ミ(Cellul−omonas fist) IPo
12107等を挙げることができる。Examples of microorganisms used in the present invention include Streptomyces griseus.
iseus) IFo 3355, Cellulomonas fimi (Cellul-omonas fist) IPo
12107 etc. can be mentioned.
これらの微生物を培養する培地としては、通常これらの
微生物が生育し得る培地にアミドあるいはニトリル化合
物を添加したものが使用される。As a medium for culturing these microorganisms, a medium in which an amide or nitrile compound is added to a medium in which these microorganisms can grow is usually used.
例えば、炭素源としてグルコース、シュークロース、グ
リセロール等、窒素源としてペプトン、肉エキス、酵母
エキス、アミノ酸、あるいは各種無機、有機酸アンモニ
ウム塩等、その他無機塩、微量金属塩、ビタミン等を必
要に応して適宜添加した培地に、アミドあるいはニトリ
ル化合物を添加したものが用いられる。For example, carbon sources include glucose, sucrose, glycerol, etc., nitrogen sources include peptone, meat extract, yeast extract, amino acids, various inorganic and organic acid ammonium salts, other inorganic salts, trace metal salts, vitamins, etc., as necessary. A medium to which an amide or nitrile compound is added is used.
添加するアミドおよびニトリル化合物は、イソブチロニ
トリル、イソブチルアミド、プロピオニトリル、プロピ
オンアミド、メタクリロニトリル、メタクリルアミド等
の脂肪族、ベンゾニトリル、ベンズアミド等の芳香族、
3−シアノピリジン、ニコチン酸アミド等の複素環化合
物などが挙げられる。The amide and nitrile compounds to be added include aliphatic compounds such as isobutyronitrile, isobutyramide, propionitrile, propionamide, methacrylonitrile, and methacrylamide; aromatic compounds such as benzonitrile and benzamide;
Examples include heterocyclic compounds such as 3-cyanopyridine and nicotinic acid amide.
培養は、培地のpH6〜10、好ましくは7〜9、温度
15〜37℃、好ましくは25〜30°Cで好気的に1
〜7日間行う。The culture is carried out aerobically at a pH of 6 to 10, preferably 7 to 9, and a temperature of 15 to 37°C, preferably 25 to 30°C.
Do this for ~7 days.
本発明において、3−シアノピリジンからニコチン酸ア
ミドを製造する方法としては、例えば、上記のようにし
て培養して得た微生物の培養液あるいは遠心分離などに
より得た菌体の懸濁液に3−シアノピリジンを添加する
方法、菌体処理物(例えば、菌体破砕物、粗酵素、精製
酵素等)あるいは常法により固定化した菌体または菌体
処理物等の懸濁液に基質を添加する方法、微生物の培養
時に基質を培養液に添加して培養と同時に反応を行う方
法等がある。In the present invention, as a method for producing nicotinic acid amide from 3-cyanopyridine, for example, 3 - A method of adding cyanopyridine, adding a substrate to a suspension of bacterial cells fixed by a method of adding cyanopyridine (e.g., crushed bacterial cells, crude enzyme, purified enzyme, etc.) or a suspension of bacterial cells or treated bacterial cells, etc. There are methods such as a method in which a substrate is added to the culture solution during culturing of microorganisms and a reaction is carried out simultaneously with the culturing.
反応液中の基質濃度が特に限定するものではないが、1
mM〜IMの範囲が好ましく、基質は反応液中に一括し
て加えるかあるいは分割添加することができる。反応温
度は5〜50°C,pHは4〜10の範囲で行うことが
好ましい。また、反応時間は基質濃度、菌体濃度、ある
いはその他の反応条件等によって変わるが、通常10分
〜48時間で終了させればよい。Although the substrate concentration in the reaction solution is not particularly limited, 1
The range of mM to IM is preferable, and the substrate can be added to the reaction solution all at once or in portions. The reaction temperature is preferably 5 to 50°C and the pH is preferably 4 to 10. Although the reaction time varies depending on the substrate concentration, bacterial cell concentration, and other reaction conditions, it is generally sufficient to complete the reaction within 10 minutes to 48 hours.
反応液からのニコチン酸アミドの回収は常法により行う
ことができる。例えば、反応液から菌体を遠心分離等に
よって除去し、反応液を濃縮乾固後、再結晶等により回
収、精製することができる。Nicotinic acid amide can be recovered from the reaction solution by a conventional method. For example, bacterial cells can be removed from the reaction solution by centrifugation or the like, the reaction solution can be concentrated to dryness, and then recovered and purified by recrystallization or the like.
次に、本発明を実施例により説明するが、本発明はこれ
らの例のみに限定されるものではない。Next, the present invention will be explained by examples, but the present invention is not limited only to these examples.
なお、ニコチン酸アミドは高速液体クロマトグラフィー
(昭和電工製5hodex F−411Aカラムを使用
)により定量した。In addition, nicotinic acid amide was quantified by high performance liquid chromatography (using a Showa Denko 5hodex F-411A column).
実施例1
ポリペプトン0.5χ、酵母エキス0,2χ、グルコー
ス0.5χ、KJPOa O,05L KHtPOa
O,05χ、Mg5Oa−7)1200.05χ、0.
042mM CoCIg、0.042+nM Fe50
..0.042mM N1Cb、0.042a+M M
nCIz、0.042+sM Cu5Oa、0.042
mM Zn5Oa、0.042mM NaffiMoO
a、0.2χプロピオニトリル、0.2χプロピオンア
ミドを含む培地でストレプトマイセス グリセウス(S
treptomycesgriseus) IFO33
55を30°Cにて48時間振盪培養して調製した洗浄
菌体(2,0mg)を10wM3−シアノピリジンを含
む0.5 dの50mMリン酸カリウム緩衝液(pH7
,2)に懸濁し25°Cにて26時間反応させた。Example 1 Polypeptone 0.5χ, yeast extract 0.2χ, glucose 0.5χ, KJPOa O,05L KHtPOa
O, 05χ, Mg5Oa-7) 1200.05χ, 0.
042mM CoCIg, 0.042+nM Fe50
.. .. 0.042mM N1Cb, 0.042a+M M
nCIz, 0.042+sM Cu5Oa, 0.042
mM Zn5Oa, 0.042mM NaffiMoO
a, Streptomyces griseus (S
treptomyces griseus) IFO33
Washed bacterial cells (2.0 mg) prepared by culturing 55 with shaking at 30°C for 48 hours were added to 0.5 d of 50 mM potassium phosphate buffer (pH 7) containing 10 wM3-cyanopyridine.
, 2) and reacted at 25°C for 26 hours.
反応終了後、菌体を遠心分離により除去し上清を調べた
ところ、0.09mMのニコチン酸アミドの生成が認め
られた。After the reaction was completed, the bacterial cells were removed by centrifugation and the supernatant was examined, and the production of 0.09 mM nicotinic acid amide was observed.
実施例2
ポリペプトンO,SZ、酵母エキス0.2χ、グルコー
ス0.5L KJPOn O,05χ、KHtPOa
O,05χ、Mg5O。Example 2 Polypeptone O, SZ, yeast extract 0.2χ, glucose 0.5L KJPOn O,05χ, KHtPOa
O,05χ, Mg5O.
−78100,05χ、 0.04211M CoC
1g、 0.042mM Fe1o4.0.0421
1M N1Ch、 0.042mM MnCIg、
0.042+gM Cu5Oa、0.042mM
Zn5Oa、0.042mM NaJoOn、0.2χ
イソブチロニトリル、0.2χイソブチルアミドを含む
培地でセルロモナス フィミ(Cellulomona
s fimi) IFO12107を30°Cにて48
時間振盪培養して調製した洗浄菌体(2,0mg)を1
0mM3−シアノピリジンを含む0、5 dの50−H
リン酸カリウム緩衝液(pH7,2)に懸濁し25°C
にて26時間反応させた0反応終了後、菌体を遠心分離
により除去し上清を調べたところ、0.05mMのニコ
チン酸アミドの生成が認められた。-78100,05χ, 0.04211M CoC
1g, 0.042mM Fe1o4.0.0421
1M N1Ch, 0.042mM MnCIg,
0.042+gM Cu5Oa, 0.042mM
Zn5Oa, 0.042mM NaJoOn, 0.2χ
Cellulomonas fimi (Cellulomona fimi) was grown in a medium containing isobutyronitrile and 0.2χ isobutyramide.
s fimi) IFO12107 at 30°C
Washed bacterial cells (2.0 mg) prepared by shaking culture for 1 hour
0,5 d of 50-H with 0 mM 3-cyanopyridine
Suspended in potassium phosphate buffer (pH 7,2) and heated at 25°C.
After 26 hours of reaction, the bacterial cells were removed by centrifugation and the supernatant was examined, and the production of 0.05 mM nicotinic acid amide was observed.
Claims (1)
りニコチン酸アミドに変換するニコチン酸アミドの製造
法において、該微生物として、セルロモナス(Cell
ulomonas)属またはストレプトマイセス(St
reptomyces)属に属し該ニトリルを水和する
能力を有する微生物を用いること、を特徴とする微生物
によるニコチン酸アミドの製造法。In the method for producing nicotinic acid amide in which 3-cyanopyridine is converted to nicotinic acid amide by a hydration reaction caused by the action of a microorganism, Cellulomonas (Cellulomonas) is used as the microorganism.
ulomonas) or Streptomyces (St
1. A method for producing nicotinic acid amide using a microorganism, the method comprising using a microorganism belonging to the genus Reptomyces and having the ability to hydrate the nitrile.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8069790A JP3035314B2 (en) | 1990-03-30 | 1990-03-30 | Microbial production of nicotinamide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8069790A JP3035314B2 (en) | 1990-03-30 | 1990-03-30 | Microbial production of nicotinamide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH03280891A true JPH03280891A (en) | 1991-12-11 |
JP3035314B2 JP3035314B2 (en) | 2000-04-24 |
Family
ID=13725522
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8069790A Expired - Lifetime JP3035314B2 (en) | 1990-03-30 | 1990-03-30 | Microbial production of nicotinamide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3035314B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5264362A (en) * | 1991-03-18 | 1993-11-23 | Lonza Ltd. | Microbiological process for the production of 6-hydroxynicotinic acid |
US5266469A (en) * | 1991-03-18 | 1993-11-30 | Lonza Ltd. | Microbiological process for the production of 6-hydroxynicotinic acid |
CN116042743A (en) * | 2022-08-11 | 2023-05-02 | 南京师范大学 | Application of adhesive arrow bacteria in preparing nicotinamide by bioconversion of 3-cyanopyridine and application method thereof |
-
1990
- 1990-03-30 JP JP8069790A patent/JP3035314B2/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5264362A (en) * | 1991-03-18 | 1993-11-23 | Lonza Ltd. | Microbiological process for the production of 6-hydroxynicotinic acid |
US5266469A (en) * | 1991-03-18 | 1993-11-30 | Lonza Ltd. | Microbiological process for the production of 6-hydroxynicotinic acid |
CN116042743A (en) * | 2022-08-11 | 2023-05-02 | 南京师范大学 | Application of adhesive arrow bacteria in preparing nicotinamide by bioconversion of 3-cyanopyridine and application method thereof |
Also Published As
Publication number | Publication date |
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JP3035314B2 (en) | 2000-04-24 |
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