Studies towards the synthetic applicability of biocatalytic allylic oxidations with the lyophilisate of Pleurotus sapidus

Weidmann, Verena; Kliewer, Serge; Sick, Marko; Bycinskij, Sergej; Kleczka, Margarethe; Rehbein, Julia; Griesbeck, Axel G.; Zorn, Holger; Maison, Wolfgang

doi:10.1016/j.molcatb.2015.07.008

Cited by 4 publications

(3 citation statements)

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“…These researches were based mainly on the fungi and bacteria-mediated chemical transformations whereas the exploitation of some specific oxido-reductases were described only recently. In particular, Aspergillus niger [13,14], Lasiodiplodia theobromae [15], Cunninghamella blakesleeana [16], Botrytis cinerea [17], Aspergillus awamori [18], Pleurotus sapidus [19], Mortierella isabellina [20] and different Streptomyces strains [21] have proved to be active biocatalysts for the transformation of these kind of compounds. Concerning the use of isolated enzymes or the exploitation of a specific enzymatic activities, both cytochrome P450 monooxygenases [22,23] and engineered whole cell biocatalysts expressing mutant P450 monooxygenases [24], were used for the oxidation of different ionone isomers.…”

Section: Introductionmentioning

confidence: 99%

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Serra

Simeis

2018

Molecules

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In this work, we describe a study on the biotransformation of seven natural occurring apocarotenoids by means of eleven selected fungal species. The substrates, namely ionone (α-, β- and γ-isomers), 3,4-dehydroionone, damascone (α- and β-isomers) and theaspirane are relevant flavour and fragrances components. We found that most of the investigated biotransformation reactions afforded oxidized products such as hydroxy- keto- or epoxy-derivatives. On the contrary, the reduction of the keto groups or the reduction of the double bond functional groups were observed only for few substrates, where the reduced products are however formed in minor amount. When starting apocarotenoids are isomers of the same chemical compound (e.g., ionone isomers) their biotransformation can give products very different from each other, depending both on the starting substrate and on the fungal species used. Since the majority of the starting apocarotenoids are often available in natural form and the described products are natural compounds, identified in flavours or fragrances, our biotransformation procedures can be regarded as prospective processes for the preparation of high value olfactory active compounds.

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Section: Introductionmentioning

confidence: 99%

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Serra

Simeis

2018

Molecules

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“…P. sapidus was also applied in the conversion of sesquiterpene, (+)-valencene to (+)-nootkatone, characterized with a grapefruit flavor even at a low odor threshold of about 1 µg/L in water [89]. The conversion was observed to be carried out through its enzyme valencene dioxygenase (ValOx) and through hydroperoxides derived from valencene, such as 6(R)-isopropenyl-4(R),4a(S)-dimethyl-2,3,4,4a,5,6,7,8octahydro-naphthalen-4(S)-yl-hydroperoxide and 6(R)-isopropenyl-4(R),4a(S)-dimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2(R)-yl-hydroperoxide, which were rapidly converted to enones [44,90]. The selective and efficient allylic oxidation of (+)-valencene to (+)nootkatone sesquiterpene was also achieved with the use of the basidiomycete, P. sapidus in its lyophilized form.…”

Section: Terpenesmentioning

confidence: 99%

Agro-Industrial Residues Used as Substrates for the Production of Bioaroma Compounds with Basidiomycetes: A Comprehensive Review

Sandes,

dos Santos,

de Jesus

et al. 2023

Fermentation

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Flavoring compounds are substances that directly influence the acceptance or rejection of a product. They are considered as essential components in the industrial sector due to their wide range of applications in different areas, such as food, cosmetics and pharmaceuticals. With the growing demand and concern of consumers for the acquisition of flavors from natural products, alternatives for the sustainable and low-cost production of such compounds becomes mandatory. Among these alternatives, biotechnological processes involving fungi are considered ecologically suitable and sustainable, as they tend to use conditions that are less harmful to the environment. The application of filamentous fungi such as basidiomycetes in biotechnological processes has been very promising, although it depends on the strain and growing conditions for obtaining bioaromas. The present review aims to compile reports on the potential of several basidiomycete fungi in the production of bioaromas using biotechnological methods. This review also includes the availability of nutrients and covers the new perspectives created with the application of agro-industrial residues as alternative cultivation substrates for these microorganisms. Thus, this is expected to consequently alleviate environmental pollution problems and enable the production of promising volatile compounds in a natural and sustainable way.

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“…For example, the biocatalytic oxidation with PSA has a relatively wide range of substrates including several functionalized terpenoids such as α -pinene (10) and theaspirane (11) ( Fraatz et al, 2009 ; Krugener et al, 2010 ; Rickert et al, 2012 ; Weidmann et al, 2015 ). In addition, PSA can also oxidize cyclohexene derivatives, but many reactions have limited regioselectivity, except that tert -butyl cyclohexene (14) was converted with good regioselectivity ( Figure 1F ).…”

Section: Whole Cell As a Catalystmentioning

confidence: 99%

Enzyme-catalyzed allylic oxidation reactions: A mini-review

et al. 2022

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Chiral allylic oxidized products play an increasingly important role in the pharmaceutical, agrochemical, and pharmaceutical industries. Biocatalytic C–H oxyfunctionalization to synthesize allylic oxidized products has attracted great attention in recent years, with the ability to simplify synthetic approaches toward complex compounds. As a result, scientists have found some new enzymes and mutants through techniques of gene mining and enzyme-directed evolution in recent years. This review summarizes the recent developments in biocatalytic selective oxidation of olefins by different kinds of biocatalysts.

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Studies towards the synthetic applicability of biocatalytic allylic oxidations with the lyophilisate of Pleurotus sapidus

Cited by 4 publications

References 50 publications

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Agro-Industrial Residues Used as Substrates for the Production of Bioaroma Compounds with Basidiomycetes: A Comprehensive Review

Enzyme-catalyzed allylic oxidation reactions: A mini-review

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