Expression, purification and functional characterization of a recombinant 2,3-dihydroxybiphenyl-1,2-dioxygenase from Rhodococcus rhodochrous

Xiong, Fei; Shuai, Jian-Jun; Peng, Ri‐He; Tian, Yong‐Sheng; Wang, Zhao; Yao, Qizheng; Xiong, Ai‐Sheng

doi:10.1007/s11033-010-0554-8

Cited by 9 publications

(5 citation statements)

References 34 publications

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“…After evaporation of 30 ml of pyridine (50°C and reduced pressure), 50 ml of ethanol is added to the resulting residue at 55°C which is kept at 0–5°C overnight and crystalline carmofur is obtained (Ozaki, 1996; Ozaki et al, 1977). Method 2 involves N‐formylation of 5‐FU in presence of aqueous formaldehyde, which follows oxidation by potassium bromate and condensation with hexyl‐amine to form carmofur (Shelton et al, 2016; Xiong et al, 2011). The details of the two routes are shown in Scheme 1.…”

Section: Chemistry and Synthesis Of Carmofurmentioning

confidence: 99%

Versatile use of Carmofur: A comprehensive review of its chemistry and pharmacology

Islam

Mirza

2022

Drug Development Research

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Carmofur, 1-hexylcarbamoyl-5-fluorouracil (HCFU) is an antineoplastic drug, which has been in clinics in Japan since 1981 for the treatment of colorectal cancer.Subsequently, it was also introduced in China, Korea, and Finland. Besides colorectal cancer, it has also shown antitumor activity in other cancers such as breast, head and neck, pancreatic, gastrointestinal, and solid brain tumors. A prodrug of 5-fluorouracil(5-FU), carmofur has shown better gastrointestinal stability and superior antiproliferative activity compared to its active counterpart 5-FU. Recently, carmofur has gained attention as an acid ceramidase inhibitor and as a potential lead compound against several noncancerous diseases such as coronavirus disease 2019, Krabbe disease, acute lung injury, Parkinson's disease, dementia, childhood ependymoma etc. Carmofur has also been reported to have antifungal, and antimicrobial properties. Nevertheless, no comprehensive review is available on this drug. Herein, we summarized the chemistry, pharmacokinetics, and pharmacology of carmofur based on the literature published between January 1976 and March 2022 as identified from PubMed and Google Scholar search engines.

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Section: Chemistry and Synthesis Of Carmofurmentioning

confidence: 99%

Versatile use of Carmofur: A comprehensive review of its chemistry and pharmacology

Islam

Mirza

2022

Drug Development Research

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“…For example, the conversion of benzoate was catalyzed by a benzoate dioxygenase with a narrow substrate scope from R. opacus 1CP [87]. 2,3-dihydroxybiphenyl-1,2-dioxygenases from Rhodococcus have been recombinantly expressed, showing activity toward a number of catechols with 2,3-dihydroxybiphenyl being the best accepted substrate [88,89] and several catechol-1,2-dioxygenases were shown to cleave (alkyl-substituted and halogenated) catechols [90,91].…”

Section: Promiscuous Redox-reactions In Rhodococcusmentioning

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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“…Although it is unclear which oxygenases in R. rhodochrous ATCC BAA-870 are catabolic and which are involved in secondary metabolism, their abundance is consistent with a potential ability to degrade an exceptional range of aromatic compounds (oxygenases catalyse the hydroxylation and cleavage of these compounds). Rhodococci are well known to have the capacity to catabolise hydrophobic compounds, including hydrocarbons and polychlorinated biphenyls (PCBs), mediated by a cytochrome P450 system [90][91][92][93]. Cytochrome P450 oxygenase is often found fused with a reductase, as in Rhodococcus sp.…”

Section: Fundamental and Applicable Biocatalytic Properties Of Rhodocmentioning

confidence: 99%

The complete genome sequence of the nitrile biocatalyst Rhodocccus rhodochrous ATCC BAA-870

Frederick

Hennessy

Horn

et al. 2019

Preprint

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Background Rhodococci are industrially important soil-dwelling Gram-positive bacteria that are well known for both nitrile hydrolysis and oxidative metabolism of aromatics. Rhodococcus rhodochrous ATCC BAA-870 is capable of metabolising a wide range of aliphatic and aromatic nitriles and amides. The genome of the organism was sequenced and analysed in order to better understand this whole cell biocatalyst. Results The genome of R. rhodochrous ATCC BAA-870 is the first Rhodococcus genome fully sequenced using Nanopore sequencing. The circular genome contains 5.9 megabase pairs (Mbp) and includes a 0.53 Mbp linear plasmid, that together encode 7548 predicted protein sequences according to BASys annotation, and 5535 predicted protein sequences according to RAST annotation. The genome contains numerous oxidoreductases, 15 identified antibiotic and secondary metabolite gene clusters, several terpene and nonribosomal peptide synthetase clusters, as well as 6 putative clusters of unknown type. The 0.53 Mbp plasmid encodes 677 predicted genes and contains the nitrile converting gene cluster, including a nitrilase, a low molecular weight nitrile hydratase, and an enantioselective amidase. Although there are fewer biotechnologically relevant enzymes compared to those found in rhodococci with larger genomes, such as the well-known Rhodococcus jostii RHA1, the abundance of transporters in combination with the myriad of enzymes found in strain BAA-870 might make it more suitable for use in industrially relevant processes than other rhodococci. Conclusions The sequence and comprehensive description of the R. rhodochrous ATCC BAA-870 genome will facilitate the additional exploitation of rhodococci for biotechnological applications, as well as enable further characterisation of this model organism. The genome encodes a wide range of enzymes, many with unknown substrate specificities supporting potential applications in biotechnology, including nitrilases, nitrile hydratase, monooxygenases, cytochrome P450s, reductases, proteases, lipases, and transaminases.

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Expression, purification and functional characterization of a recombinant 2,3-dihydroxybiphenyl-1,2-dioxygenase from Rhodococcus rhodochrous

Cited by 9 publications

References 34 publications

Versatile use of Carmofur: A comprehensive review of its chemistry and pharmacology

Versatile use of Carmofur: A comprehensive review of its chemistry and pharmacology

Rhodococcus as A Versatile Biocatalyst in Organic Synthesis

The complete genome sequence of the nitrile biocatalyst Rhodocccus rhodochrous ATCC BAA-870

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