The reducing capacities of cyanobacteria for aldehydes and ketones

Jüttner, Friedrich; Hans, Robert T.

doi:10.1007/bf00252512

Cited by 18 publications

(16 citation statements)

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“…2 However, phototrophic prokaryotes such as cyanobacteria have also been identified as a source of reductive activities, but in contrast to other extensively studied bacteria and fungi, this field is still poorly investigated. 3,4 Biocatalysis is an effective and, in many cases, preferable alternative to the standard synthesis of optically active isomers of valuable chemicals, including phosphonates of a defined structure and absolute configuration. 5 Hydroxyphosphonates are a class of organophosphorus compounds with possible biological activity -they represent a synthetic platform for further applications (e.g.…”

Section: Introductionmentioning

confidence: 99%

Application of cyanobacteria for chiral phosphonate synthesis

Górak

Żymańczyk–Duda

2015

Green Chem.

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This is the first report on morphologically different strains of cyanobacteria: Arthrospira maxima, Nostoc cf-muscorum and Nodularia sphaerocarpa used for enantioselective bioreduction of selected, structurally different diethyl esters of oxophosphonic acids. The efficiency of the asymmetric hydrogen transfer was strongly dependent on the chemical structure of the substrates. Arthrospira maxima was active only toward diethyl (S)-2-oxopropylphosphonate (20% of yield, 99% of ee), whereas the application of Nostoc cf-muscorum as a biocatalyst allowed diethyl (S)-2-hydroxy-2-phenylethylphosphonate with a high enantiomeric excess (99%) and with 26% conversion degree to be obtained. Employing Nodularia sphaerocarpa led to the most spectacular result -diethyl (S)-2-hydroxy-2-phenylethylphosphonate with a degree of conversion of 99% and an optical purity of 92%. Enantioselective bioconversion of oxophosphonate with an aromatic side group located in the immediate vicinity of the carbonyl functionality was achieved for the first time. Additionally, flow cytometry showed excellent resistance of the cells of Nodularia sphaerocarpa against the examined xenobiotic -2-oxo-2-phenylethylphosphonate, these cells remain viable at the concentration of 10 mM of the bioconversion substrate compared to the 1 mM described previously for a fungal biocatalyst. The effect of cultivation medium, light source and light cycle (light : dark) on the effectiveness of the biotransformation process was examined.

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Section: Introductionmentioning

confidence: 99%

Application of cyanobacteria for chiral phosphonate synthesis

Górak

Żymańczyk–Duda

2015

Green Chem.

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“…25 Alcohol dehydrogenase is thought to exist in cyanobacteria. 26 A further reduction to 2,3-hexandiol was also found in the biotransformation experiments. However, the reduction can not be catalysed by either of the two enzymes mentioned above.…”

Section: Discussionmentioning

confidence: 65%

Off-flavours in water: hydroxyketones andβ-ionone derivatives as new odour compounds of freshwater cyanobacteria

Höckelmann

Jüttner

2005

Flavour Fragr. J.

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Cyanobacteria essentially contribute to the off-flavours of drinking water and freshwater fish. They are primary nuisance microorganisms and their control in lakes and ponds used for the production of drinking water and fish farming is expensive. We describe new odour compounds of freshwater cyanobacteria that are fermentation products and norcarotenoids. These may contribute to the off-flavours frequently observed with cyanobacteria. The fermentation products were represented by 2,3-pentandione, 2,3-hexandione, 2-hydroxy-3-pentanone, 3-hydroxy-2-pentanone, 2-hydroxy-3-hexanone, 3-hydroxy-2-hexanone and 2,3-hexandiol. These compounds are important for odour quality in microbially-processed dairy food, caused by the metabolism of fungi and heterotrophic bacteria. Their cyanobacterial synthesis was shown by 13 C-labelling, growth kinetics and biotransformation experiments. The labelled mass spectra of the hydroxyketones showed unequivocally the cyanobacterial rather than bacterial origin of the compounds. Norcarotenoids of the β β β β β-ionone-type (β β β β β-ionol, β β β β β-ionone-5,6-epoxide, dihydro-β β β β β-ionone, dihydro-β β β β β-ionol, tetrahydroionone, 4-oxo-β β β β β-ionone and 2,4,4-trimethyl-3-(3-oxobutyl)-2-cyclohexen-1-one) were another important group of compounds that were found in axenic cyanobacterial cultures and a monoxenic culture of Phormidium sp. The results implicate the presence of further oxygenases in cyanobacteria. Except for tetrahydroionone, the syntheses of the β β β β β-ionone derivatives were established by biotransformation experiments applying the precursor β β β β β-ionone. The norcarotenoid 6-methyl-5-hepten-2-one, which is regarded as a precursor compound of 1,3,3-trimethyl-2,7-dioxabicylo(2,2,1)heptane (TDH), was 13 C-labelled, while TDH did not show any labelling. There is evidence that TDH arises from the analytical procedure and is an artefact rather than a biogenic compound produced by the cyanobacteria.

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“…Literature data show the ability of cyanobacteria Synechococcus PCC 6911 to reduce geranial ( 1 ) to geraniol ( 2 ) after 7 days of incubation (Jϋttner and Hans ). Geranial is E ‐isomer of citral and is used as an aroma fragrant component in perfumery due to its citrus scent.…”

Section: Biotransformation Of Monoterpenes By Cyanobacteriamentioning

confidence: 99%

“…These two molecules differ only in the presence or absence of a double bond in the side chain extending from the C‐2 ring atom. Unfortunately, authors did not provide the absolute configuration of products of biotransformations (Jϋttner and Hans ).…”

Section: Biotransformation Of Monoterpenes By Cyanobacteriamentioning

confidence: 99%

Biotransformations of monoterpenes by photoautotrophic micro-organisms

et al. 2014

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Summary Monoterpenes are widely used in food technology, cosmetic and pharmaceutical industries and as compounds of agricultural importance. It is known that compounds comprising this class can be transformed by a variety of organisms, namely by: bacteria, fungi, yeasts, plants or isolated enzymes. Biotransformations, as one of the most important tools of green chemistry, allow obtaining new products using whole cells of micro‐organisms or isolated enzymes in mild reaction conditions. Therefore, biotransformations of monoterpenes, by different type of reaction such as: epoxidation, oxidation and stereoselective hydroxylation, resulted in the production of so desired, enantiomerically defined compounds that can be advised as natural seem to be interesting. Bearing in mind that such processes are carried out also by easy to maintain, photoautotrophic micro‐organisms cultivated at large scale, this paper is focused on biotransformations of acyclic, monocyclic and bicyclic monoterpenes by freshwater or haliphylic cyanobacteria and microalgae on the way of mainly stereoselective hydroxylation. Moreover, aspects of potential industrial application of obtained products in medicine, perfume, cosmetics and food industry are discussed.

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The reducing capacities of cyanobacteria for aldehydes and ketones

Cited by 18 publications

References 1 publication

Application of cyanobacteria for chiral phosphonate synthesis

Application of cyanobacteria for chiral phosphonate synthesis

Off-flavours in water: hydroxyketones andβ-ionone derivatives as new odour compounds of freshwater cyanobacteria

Biotransformations of monoterpenes by photoautotrophic micro-organisms

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