Enzymatic synthesis of an important building block for the new nicotinyl pesticides
新型烟基农药重要组成部分的酶法合成
基本信息
- 批准号:07556025
- 负责人:
- 金额:$ 5.38万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Scientific Research (A)
- 财政年份:1995
- 资助国家:日本
- 起止时间:1995 至 1996
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
Various pyridine derivatives have physiological activity. Very recently, the new powerful insecticides belonging to nicotinly group, have been found. These nicotinly insecticides are expected to be popular due to the powerful activity and low toxicity. However, it is not easy to synthesize the building block of 6-chloropyridyl through the conventional chemical synthesis. Thus, the development of the new bioprocess for the synthesis of the building block is required. To accomplish this purpose, we investigated the enzymatic regio-specific hydroxylation reaction of pyridine ring. Once the pyridine ring is hydroxylated, the halogenation of pyridine ring can be proceeded easily.We have focused on the regiospecific hydroxylation reaction of pyridine ring for two years. We attempted to isolate the microorganisms which catalyze the regiospecific hydroxylation of nicotinic acid. We found Pseudomonas fluorescens TN5 catalyzes the 6-position specific hydroxylation of nicotinic acid. We optimized … More the culture conditions to enhance the hydroxylation reaction. When the resting cells were added to the reaciton mixture containing nicotinic acid with aerobically shaking, and enormous amount of 6-hydroxynicotinic acid accumulated with the high molecular conversion yield. We also found the microorganism to catalyze the 6-position hydroxylation reaction of 3-cyanopyridine to form 3-cyano-6-hydroxypyridine. 6-Hydroxynicotinic acid and 3-cyano-6-hydroxypyridine are useful for the synthesis of the building block of the new nicotinyl insecticides. The enormous high yield suggests the high possibility of this process for industrail use.Further, we elucidated the enzymes to catalyze the regio-specific hydroxylation of nicotinic acid. The dehydrogenase, coupled to cytochrome oxidase, is responsible for this hydroxylation. When the resting cells and the substrate are incubated aerobically, the hydroxylation reaction proceeded efficiently.Further, we attempted to establish the new enzymatic production process of d-aminolevurilic acid, which is promising as the new plant hormon. P.fluorescens catalyzes the conversion of 6-hydroxynicotinic acid into 2,5-dihydroxypyridine, which can be synthesized easily through chemical way into delta-aminolevurilic acid. We purified and characterized the enzyme which catalyzed the conversion of 6-hydroxynicitnic acid into 2,5-dihydroxypyridine. We elucidated that the new monooxygenase is responsible for this decarboxylative hydroxylation reaction. We also optimized the reaction conditions for the production of 2,5-dihydroxypyridine using the monooxygenase. Thus, we have established the new biological production process for the synthesis of delta-aminolevurilic acid. Less
各种吡啶类化合物都具有生理活性。最近,人们发现了属于尼古丁基团的新型强效杀虫剂。这些烟碱类杀虫剂由于活性强、毒性低,有望得到广泛应用。然而,通过传统的化学合成方法合成6-氯吡啶的构筑基团并不容易。因此,需要开发用于合成构建块的新的生物工艺。为了实现这一目的,我们研究了吡啶环的酶促区域特异性羟基化反应。吡啶环一旦发生羟化反应,就可以很容易地进行卤化反应。两年来,我们一直致力于吡啶环的区域特异性羟基化反应。我们试图分离出催化烟酸区域特异性羟基化的微生物。我们发现荧光假单胞菌Tn5催化烟酸的6位特异性羟化。我们优化了…更多的培养条件有利于增强羟基化反应。在含有烟酸的反应混合物中加入休眠细胞,经好氧振荡后,6-羟基烟酸大量积累,分子转化率高。我们还发现该微生物能够催化3-氰基-6-羟基吡啶的6位羟基化反应生成3-氰基-6-羟基吡啶。6-羟基烟酸和3-氰基-6-羟基吡啶是合成新型烟碱类杀虫剂的重要原料。极高的产率表明该工艺工业化应用的可能性很高。此外,我们还阐明了催化烟酸区域特异性羟化的酶。脱氢酶与细胞色素氧化酶偶联,负责这种羟化作用。在休眠细胞和底物的有氧培养下,羟基化反应有效进行,并尝试建立新的酶法生产D-氨基酮尿酸的新工艺,有望作为新的植物激素。荧光假单胞菌催化6-羟基烟酸转化为2,5-二羟基吡啶,而2,5-二羟基吡啶可以通过化学方法很容易地合成β-氨基酮尿酸。我们对催化6-羟基烟酸转化为2,5-二羟基吡啶的酶进行了纯化和鉴定。我们阐明了这种新的单加氧酶负责这种脱羧羟化反应。并对单加氧酶催化合成2,5-二羟基吡啶的反应条件进行了优化。从而建立了合成β-氨基酮尿酸的生物生产新工艺。较少
项目成果
期刊论文数量(25)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Katsumi Takayama, Toshiharu Kurozaki, Tokuji Ikeda and Toru Nagasawa: "Bioelectrocatalytic Hydroxylation of Nicotinic Acid at an Electrode Modified with Immobilized Bacterial Cells of Pseudomonas fluorescens in the Presence of Electron Transfer Mediators.
Katsumi Takayama、Toshiharu Kurozaki、Tokuji Ikeda 和 Toru Nagasawa:“在存在电子转移介体的情况下,在用荧光假单胞菌固定化细菌细胞修饰的电极上进行烟酸的生物电催化羟基化。
- DOI:
- 发表时间:
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- 影响因子:0
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- 通讯作者:
Mari Yasuda: "Microbial Hydroxylation of 3-Cyanopyridine to 3-Cyano-6-hydroxypyridine" Biosci. Biotech. Biochem.59. 572-575 (1995)
Mari Yasuda:“3-氰基吡啶微生物羟基化为 3-氰基-6-羟基吡啶”Biosci。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
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Katsumi Takayama: "Bioelectrocatalytic Hydroxylation of Nicotinic Acid at an Electrode modified with Immobilized Bacterial Cells of P. fluoroscens in the presence of." J. Electroanalytical Chem.381. 47-53 (1995)
Katsumi Takayama:“在存在荧光假单胞菌固定化细菌细胞的情况下,在电极上进行烟酸的生物电催化羟基化。”
- DOI:
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- 影响因子:0
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高山勝巳: "Mediated Amperometric Biosensor for Nicotinic Acid Based on Whole-Cells of Pseudomonas fluorescens." Electroanal. 8. 765-788 (1996)
Katsumi Takayama:“基于荧光假单胞菌全细胞的烟酸介导电流生物传感器”,8. 765-788 (1996)。
- DOI:
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- 影响因子:0
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Bungserk Hurh, Tsuneo Yamane, Toru Nagasawa: "Purification and Characterization of Nicotinic Acid Dehydrogenase from Pseudomonas fluorescens TN5." J.Ferment.Bioeng.78. 19-26 (1994)
Bungserk Hurh、Tsuneo Yamane、Toru Nagasawa:“荧光假单胞菌 TN5 中烟酸脱氢酶的纯化和表征。”
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NAGASAWA Toru其他文献
Association between Job Stress and Number of Physical Symptoms among Female Nurses of Medical-university-affiliated Hospitals
医科大学附属医院女护士工作压力与躯体症状数的相关性
- DOI:
10.1265/jjh.73.388 - 发表时间:
2018 - 期刊:
- 影响因子:0
- 作者:
YOSHIOKA Nozomi;NOMURA Kyoko;ASAYAMA Kei;TAKENOSHITA Shinichi;NAGASAWA Toru;NAKATA Yoshinori;HIRAIKE Haruko;SASAMORI Yukifumi;TSUCHIYA Akiko;OHKUBO Takayoshi;OKINAGA Hiroko - 通讯作者:
OKINAGA Hiroko
NAGASAWA Toru的其他文献
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{{ truncateString('NAGASAWA Toru', 18)}}的其他基金
Library construction of decarboxylases catalyzing carbon dioxide fixation and their application for the production of various aromatic carboxylic acids
催化二氧化碳固定的脱羧酶文库构建及其在多种芳香族羧酸生产中的应用
- 批准号:
21580091 - 财政年份:2009
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Studies on Kolbe・Schmitt Reaction catalyzed by microbial decarboxylases and its application for the production of aromatic hydroxy carboxylic acids
微生物脱羧酶催化科尔贝·施密特反应及其在芳香族羟基羧酸生产中的应用研究
- 批准号:
19580087 - 财政年份:2007
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Highly functional utilization of surplus renewable resources through microbial regio-specific hydroxylation
通过微生物区域特异性羟基化对剩余可再生资源进行高度功能化利用
- 批准号:
14560062 - 财政年份:2002
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Findinf of novel decarboxylases which catalyzes carbon dioxide fixation and establishment of the precise conversion techniques of carbon dioxide
催化二氧化碳固定的新型脱羧酶的发现及二氧化碳精准转化技术的建立
- 批准号:
12559003 - 财政年份:2000
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Scientific Research (B)
Construction of library of useful nitrile hydratase for various industrial needs
构建适合各种工业需求的有用腈水合酶库
- 批准号:
11660080 - 财政年份:1999
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
The novel hydroxylation reaction of nicotinic acid catalyzed by the cooperation of yeat and bacteria
酵母与细菌协同催化烟酸羟基化反应
- 批准号:
09660093 - 财政年份:1997
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
New Function of Halohydrin Epoxidase and Its Application of the Synthesis of Chiral Building Block.
卤代醇环氧化酶的新功能及其在手性构件合成中的应用。
- 批准号:
05660088 - 财政年份:1993
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)
Studies on the cofactors and reaction mechanisms of nitrile hydratase which is useful for the synthesis of amides
用于酰胺合成的腈水合酶的辅因子和反应机制的研究
- 批准号:
02660114 - 财政年份:1990
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)
Develop a new technique for measuring tongue and mandibular movement
开发测量舌头和下颌运动的新技术
- 批准号:
63870075 - 财政年份:1988
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for Developmental Scientific Research
Enzymatic transformation of -chloroalanine into useful amino acids
将β-氯丙氨酸酶促转化为有用的氨基酸
- 批准号:
61560117 - 财政年份:1986
- 资助金额:
$ 5.38万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)