Stereoselective reduction of ketones by Daucus carota hairy root cultures

Caron, Dave; Coughlan, Andrew P.; Simard, Mathieu; Bernier, Jonathan; Piché, Yves; Chênevert, Robert

doi:10.1007/s10529-005-5187-y

Cited by 34 publications

(14 citation statements)

References 13 publications

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“…The present observations substantiate earlier findings related to ketone biotransformation mediated through Daucas carota [19] and Raphanus sativus [20] hairy root cultures along with that through several fungi (viz. Penicillium miczynskii Gc5, Trichoderma sp.…”

Section: Resultssupporting

confidence: 92%

Atropa belladonna Hairy Roots: Orchestration of Concurrent Oxidation and Reduction Reactions for Biotransformation of Carbonyl Compounds

Srivastava

Negi

Ajayakumar

et al. 2012

Appl Biochem Biotechnol

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The biotransformation potential of a selected Atropa belladonna hairy root clone (AB-09) had been evaluated with regard to three different aromatic carbonyl compounds, i.e., 3,4,5-trimethoxybenzaldehyde (1), 3,4,5-trimethoxyacetophenone (2), and 3,4,5-trimethoxy benzoic acid (3). The results demonstrated for the first time the untapped potentials of the selected hairy root clone to perform simultaneous oxidation (34.49%) and reduction (32.68%) of 3,4,5-trimethoxy benzaldehyde (1) into 3,4,5-trimethoxy benzoic acid (3), and 3,4,5-trimethoxy benzyl alcohol (4), respectively, without any intermediate separation or addition of reagents. The same hairy root clone also demonstrated reduction (<5%) of a 3,4,5-trimethoxyacetophenone (2) into a secondary alcohol, i.e., 1-(3,4,5-trimethoxyphenyl) ethanol (5), while in the case of aromatic carboxylic acid substrate (3), no biotransformation could be obtained under the similar conditions. The current observations revealed oxidation and reduction of the formyl group of the aromatic ring, and only reduction of the carbonyl group of acetophenone through the specific hairy root clone. The concurrent oxidation and reduction reactions by the selected hairy root clone highlight the importance of this study, which, as per our observations, is the first of its kind relating the hairy root culture of A. belladonna.

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Section: Resultssupporting

confidence: 92%

Atropa belladonna Hairy Roots: Orchestration of Concurrent Oxidation and Reduction Reactions for Biotransformation of Carbonyl Compounds

Srivastava

Negi

Ajayakumar

et al. 2012

Appl Biochem Biotechnol

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“…For instance, in hairy root cultures of Daucus carota (carrot), the supplemented prochiral ketone acetophenone was reduced to 1-phenylethanol, consisting of more than 98% of the S-isomer. 51…”

Section: Biotransformationmentioning

confidence: 99%

Combinatorial biosynthesis in plants: A (p)review on its potential and future exploitation

2011

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“…13 C-NMR d: 72.1, 50.8, 38.1, 34.9, 26.4, 8.5, 7.7 ppm. GCMS: 129 (7), 126 (6), 115(42), 97 (12), 73(53), 72 (19), 58 (5), 57(100), 55 (14), 43(49).…”

Section: -Hydroxy-5-methyl-3-heptanone (3)mentioning

confidence: 99%

“…liquid crystals), flavours and fragrances. 8,9,11, 12 Cell cultures as well as wild tissue have been used, not only for reduction of aldehydes and ketones, but also in other reactions e.g. hydrolysis of enol acetates 3 and certain other acetate esters, 13-16 reduction of carboxylic acids 17 and oxidation of alcohols.…”

Section: Introductionmentioning

confidence: 99%

Vegetables as biocatalysts in stereoselective hydrolysis of labile organic compounds

Bohman¹,

Cavonius²,

Unelius

2009

Green Chem.

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Hydrolysis of labile esters of b-hydroxyketones has been performed with whole plant tissue from various vegetables. The pheromone 5-hydroxy-4-methyl-3-heptanone (1) was used as the model compound. Hydrolysis of acetates and benzoates of 1 was unsuccessful using normal conditions of ester hydrolysis, both by chemical hydrolysis and by the means of commercial lipases. When, however, whole cells of carrot, celery root, eggplant, parsley root, parsnip and potato were used as reagents, hydrolysis of the acetates was successful. At low conversion the hydrolysis was stereoselective and at total conversion virtually no formation of by-products was observed. The selectivity varied among the eight vegetables that were evaluated. Methods of preparation and substrate-to-plant ratio were examined. Furthermore, acetates and benzoates of three analogous compounds [5-hydroxy-3-heptanone (2), 5-hydroxy-5-methyl-3-heptanone (3) and 5-ethyl-6-hydroxy-4-octanone (4)] were hydrolyzed by potato and sweet potato to various degrees, indicating that the method is general for the mild and stereoselective hydrolysis of secondary b-alkoxy-and b-aryloxyketones.

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Stereoselective reduction of ketones by Daucus carota hairy root cultures

Cited by 34 publications

References 13 publications

Atropa belladonna Hairy Roots: Orchestration of Concurrent Oxidation and Reduction Reactions for Biotransformation of Carbonyl Compounds

Atropa belladonna Hairy Roots: Orchestration of Concurrent Oxidation and Reduction Reactions for Biotransformation of Carbonyl Compounds

Combinatorial biosynthesis in plants: A (p)review on its potential and future exploitation

Vegetables as biocatalysts in stereoselective hydrolysis of labile organic compounds

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