Recent advances in biocatalyst discovery, development and applications

Yang, Guang; Ding, Yousong

doi:10.1016/j.bmc.2014.06.033

Cited by 32 publications

(28 citation statements)

References 126 publications

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“…In this review, however, we will discuss mainly the processes of oxygenation of carbon-hydrogen bonds to afford compounds with C-O bonds. All hydrocarbon oxidations occurring in living organisms [1,[20][21][22][23][24][25][26][27][28][29] from the mechanistic point of view are also of the second or third types. Some non-organometallic complexes, for example, metal derivatives of porphyrins can play the role of models of certain metal-containing enzyme centers.…”

Section: Scheme 2 Three Types Of Metal-mediated C-h Functionalizationmentioning

confidence: 99%

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

Shul’pin

2016

Catalysts

174

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This review describes new reactions catalyzed by recently discovered types of metal complexes and catalytic systems (catalyst + co-catalyst). Works of recent years (mainly 2010-2016) devoted to the oxygenations of saturated, aromatic hydrocarbons and other carbon-hydrogen compounds are surveyed. Both soluble metal complexes and solid metal compounds catalyze such transformations. Molecular oxygen, hydrogen peroxide, alkyl peroxides, and peroxy acids were used in these reactions as oxidants.

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Section: Scheme 2 Three Types Of Metal-mediated C-h Functionalizationmentioning

confidence: 99%

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

Shul’pin

2016

Catalysts

174

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“…Oxygenases, which catalyze the addition of oxygen atoms into many organic compounds, show a remarkable enantio- and regio-selectivity and broad substrate specificity [7,8,9,10]. These features make them valuable biocatalysts for the production of synthons relevant for pharmaceutical and chemical industries [4], and it has been suggested that the use of these enzymes will be as prominent as the well-established hydrolases and dehydrogenases [7].…”

Section: Introductionmentioning

confidence: 99%

“…These features make them valuable biocatalysts for the production of synthons relevant for pharmaceutical and chemical industries [4], and it has been suggested that the use of these enzymes will be as prominent as the well-established hydrolases and dehydrogenases [7]. Furthermore, their application in chemical synthesis can replace the use of potentially harmful chemicals (i.e., green chemistry) [8]. Among the most promising group of oxygenases are the Baeyer–Villiger Monooxygenases (BVMOs), well known for their biotechnological potential in the development of pharmaceuticals [11], as well as bacterial cytochrome P450 Monooxygenases (CYP153) [12], which are novel P450 and unique enzymes of the family being soluble and able to hydroxylate highly hydrophobic alkanes [13].…”

Section: Introductionmentioning

confidence: 99%

Prospecting Biotechnologically-Relevant Monooxygenases from Cold Sediment Metagenomes: An In Silico Approach

et al. 2017

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The goal of this work was to identify sequences encoding monooxygenase biocatalysts with novel features by in silico mining an assembled metagenomic dataset of polar and subpolar marine sediments. The targeted enzyme sequences were Baeyer–Villiger and bacterial cytochrome P450 monooxygenases (CYP153). These enzymes have wide-ranging applications, from the synthesis of steroids, antibiotics, mycotoxins and pheromones to the synthesis of monomers for polymerization and anticancer precursors, due to their extraordinary enantio-, regio-, and chemo- selectivity that are valuable features for organic synthesis. Phylogenetic analyses were used to select the most divergent sequences affiliated to these enzyme families among the 264 putative monooxygenases recovered from the ~14 million protein-coding sequences in the assembled metagenome dataset. Three-dimensional structure modeling and docking analysis suggested features useful in biotechnological applications in five metagenomic sequences, such as wide substrate range, novel substrate specificity or regioselectivity. Further analysis revealed structural features associated with psychrophilic enzymes, such as broader substrate accessibility, larger catalytic pockets or low domain interactions, suggesting that they could be applied in biooxidations at room or low temperatures, saving costs inherent to energy consumption. This work allowed the identification of putative enzyme candidates with promising features from metagenomes, providing a suitable starting point for further developments.

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“…They are particularly promising candidates for monoterpene biohydroxylations because of their relatively high activity and substrate specificity toward a number of monoterpenes (11,20). With the recent availability of extensive metagenomic data, the number of gene sequences potentially encoding P450s has increased substantially (22); however, many of the identified genes remain uncharacterized. The isolation and detailed characterization of enzymes is a prerequisite for optimization and use in biocatalytic reactions, paving the way for applications in synthetic biology.…”

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confidence: 99%

CYP101J2, CYP101J3, and CYP101J4, 1,8-Cineole-Hydroxylating Cytochrome P450 Monooxygenases from Sphingobium yanoikuyae Strain B2

Unterweger

Bulach

Scoble

et al. 2016

Appl Environ Microbiol

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We report the isolation and characterization of three new cytochrome P450 monooxygenases: CYP101J2, CYP101J3, and CYP101J4. These P450s were derived from Sphingobium yanoikuyae B2, a strain that was isolated from activated sludge based on its ability to fully mineralize 1, 8 T he bicyclic monoterpenoid 1,8-cineole (1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane) is a chemically stable saturated ditertiary ether (1) that is an abundant natural resource. It is a major component of many essential oils, in particular Eucalyptus oil (2). While 1,8-cineole has its main applications in pharmaceutical, fragrance, food, and cleaning industries, its oxidation provides a potential route to value-added chemicals. Hydroxylated 1,8-cineole derivatives are chiral compounds that can serve as building blocks and precursors with uses in organic chemistry (3). Hydroxylation of 1,8-cineole can be achieved chemically; however, these reactions often use a range of environmentally hazardous reagents and/or yield product mixtures (4-6). On the other hand, biooxygenation of 1,8-cineole using enzymes or whole cells can be performed under mild reaction conditions with the potential to yield products with high enantiopurity (6, 7).A potential route to bio-derived 1,8-cineole derivatives is the utilization of enzymes involved in bacterial 1,8-cineole metabolism. Bacterial 1,8-cineole metabolism was first examined in the late 1970s, when the isolation of a Pseudomonas flava strain capable of growing on 1,8-cineole as a sole source of carbon was reported (8). Subsequently, 1,8-cineole biohydroxylation has also been observed in several other bacterial species, including Rhodococcus sp. strain C1 (9), Bacillus cereus (10), Citrobacter braakii (11), Novosphingobium subterranea (12), and a Sphingomonas species (13). The first bacterial 1,8-cineole-hydroxylating enzyme which was isolated and characterized was isolated from C. braakii (11). The initial oxidation of 1,8-cineole by this Gram-negative bacterium is catalyzed by a P450 designated P450 cin (CYP176A1), and with the aid of suitable electron transport partners it yielded (1R)-6␤-hydroxy-1,8-cineole (7, 11). More recently, other P450s, including CYP101A1, CYP101B1, and the N252A P450 cin mutant,

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Recent advances in biocatalyst discovery, development and applications

Cited by 32 publications

References 126 publications

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

Prospecting Biotechnologically-Relevant Monooxygenases from Cold Sediment Metagenomes: An In Silico Approach

CYP101J2, CYP101J3, and CYP101J4, 1,8-Cineole-Hydroxylating Cytochrome P450 Monooxygenases from Sphingobium yanoikuyae Strain B2

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