Highly chemoselective and efficient production of 2,6-difluorobenzamide using Rhodococcus ruber CGMCC3090 resting cells

Tang, Rui; Shen, Yanbing; Zhai, Ying; Gao, Qian

doi:10.1016/j.jbiosc.2017.07.001

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…Since NHase exhibits high regioselectivity during the aliphatic or aromatic dinitrile catalysis process, it has great potential to replace traditional chemical hydration of dinitriles, which is virtually impossible to show regioselectivity (Table 2; Meth-Cohn and Wang, 1997;Dadd et al, 2001;Li et al, 2001). One of the most representative examples is the enzymatic production of 5-cyanovaleramide using NHase, which demonstrates higher conversion, higher selectivity, and fewer by-products (DiCosimo et al, 1998;Hann et al, 1999;Shen et al, 2012b;Chen et al, 2013a). In addition, an NHase isolated from Rhodococcus aetherivorans ZJB1208, was reported to possess the ability to regioselectively biotransform 1-cyanocyclohexaneacetonitrile into 1-cyanocyclohexaneacetamide with a biocatalyst yield (g product /g cat ) of 204.2.…”

Section: Biochemical Properties Of Nhase Regioselectivitymentioning

confidence: 99%

Recent Advances and Promises in Nitrile Hydratase: From Mechanism to Industrial Applications

Cheng

Xia

Zhou

2020

Front. Bioeng. Biotechnol.

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Nitrile hydratase (NHase, EC 4.2.1.84) is one type of metalloenzyme participating in the biotransformation of nitriles into amides. Given its catalytic specificity in amide production and eco-friendliness, NHase has overwhelmed its chemical counterpart during the past few decades. However, unclear catalytic mechanism, low thermostablity, and narrow substrate specificity limit the further application of NHase. During the past few years, numerous studies on the theoretical and industrial aspects of NHase have advanced the development of this green catalyst. This review critically focuses on NHase research from recent years, including the natural distribution, gene types, posttranslational modifications, expression, proposed catalytic mechanism, biochemical properties, and potential applications of NHase. The developments of NHase described here are not only useful for further application of NHase, but also beneficial for the development of the fields of biocatalysis and biotransformation.

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Section: Biochemical Properties Of Nhase Regioselectivitymentioning

confidence: 99%

Recent Advances and Promises in Nitrile Hydratase: From Mechanism to Industrial Applications

Cheng

Xia

Zhou

2020

Front. Bioeng. Biotechnol.

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“…NHases are versatile enzymes that accept a broad range of different nitriles. The hydrolysis of aromatic and arylalkyl nitriles was intensively studied and proven successful for pyridyl-, pyrazinyl-, (substituted) benzyl-, furyl-, and thionyl-moieties [128,129,130,131,132,133] as well as trans-2,3-epoxy-3-aryl-propannitriles [134] or rac -mandelonitrile [135]. R. boritolerans FW815 was shown to have a strong 2,2-dimethyl-c-propanecarbonitrile (DMCPCN) hydratase activity in the absence of amidase activity, leading to an enrichment of 2,2-dimethyl-c-propanecarboxamide (DMCPCA)—an important precursor for the drug cilastatin, which is an inhibitor of a renal peptidase that is involved in the metabolism of other drugs, thereby making these other, combined drugs more effective [136].…”

Section: Enzymes From the Aldoxime-nitrile Pathwaymentioning

confidence: 99%

Rhodococcus as a Versatile Biocatalyst in Organic Synthesis

Busch

Hagedoorn

Hanefeld

2019

IJMS

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The application of purified enzymes as well as whole-cell biocatalysts in synthetic organic chemistry is becoming more and more popular, and both academia and industry are keen on finding and developing novel enzymes capable of performing otherwise impossible or challenging reactions. The diverse genus Rhodococcus offers a multitude of promising enzymes, which therefore makes it one of the key bacterial hosts in many areas of research. This review focused on the broad utilization potential of the genus Rhodococcus in organic chemistry, thereby particularly highlighting the specific enzyme classes exploited and the reactions they catalyze. Additionally, close attention was paid to the substrate scope that each enzyme class covers. Overall, a comprehensive overview of the applicability of the genus Rhodococcus is provided, which puts this versatile microorganism in the spotlight of further research.

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Nitrile Metabolizing Enzymes in Biocatalysis and Biotransformation

Bhalla

Kumar

Thakur

et al. 2018

Appl Biochem Biotechnol

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Nitrile metabolizing enzymes, i.e., aldoxime dehydratase, hydroxynitrile lyase, nitrilase, nitrile hydratase, and amidase, are the key catalysts in carbon nitrogen triple bond anabolism and catabolism. Over the past several years, these enzymes have drawn considerable attention as prominent biocatalysts in academia and industries because of their wide applications. Research on various aspects of these biocatalysts, i.e., sources, screening, function, purification, molecular cloning, structure, and mechanisms, has been conducted, and bioprocesses at various scales have been designed for the synthesis of myriads of useful compounds. This review is focused on the potential of nitrile metabolizing enzymes in the production of commercially important fine chemicals such as nitriles, carboxylic acids, and amides. A number of opportunities and challenges of nitrile metabolizing enzymes in bioprocess development for the production of bulk and fine chemicals are discussed.

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Highly chemoselective and efficient production of 2,6-difluorobenzamide using Rhodococcus ruber CGMCC3090 resting cells

Cited by 4 publications

References 23 publications

Recent Advances and Promises in Nitrile Hydratase: From Mechanism to Industrial Applications

Recent Advances and Promises in Nitrile Hydratase: From Mechanism to Industrial Applications

Rhodococcus as a Versatile Biocatalyst in Organic Synthesis

Nitrile Metabolizing Enzymes in Biocatalysis and Biotransformation

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