Enantioselective hydrolysis of racemic 1-phenylethyl acetate by an enzymatic system from fresh vegetables

Vandenberghe, Alécia; Markó, István E.; Lucaccioni, Fabio; Lutts, Stanley

doi:10.1016/j.indcrop.2012.06.003

Cited by 25 publications

(9 citation statements)

References 21 publications

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“…SCSIO 15121 to obtain (R)-2 with the conversion rate 49%. Application of the enzymatic system of vegetables to the kinetic resolution of 1 was reported by Vanderberghe et al [37]. The highest ee of hydrolysis products was obtained by using beetroot as a biocatalyst (ee of (R)-2 66%, (S)-1 >99%).…”

Section: Kinetic Resolution Of 1-phenylethyl Acetate (1)mentioning

confidence: 89%

Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation

et al. 2018

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A novel microbial approach to the production of enantiomerically enriched and pure aroma compounds based on kinetic resolution via solid-state fermentation is proposed. Twenty-five filamentous fungi were screened for lipase activity and enantioselective hydrolysis of a volatile racemic ester (1-phenylethyl acetate (1)) and several racemic lactones (trans and cis whisky lactones (4, 5), γ-decalactone (7), δ-decalactone (8), (cis-3a,4,7,7a-tetrahydro-1(3H)-isobenzofuranone) (9)). Solid-state fermentation was conducted with linseed and rapeseed cakes. Kinetic resolution afforded enantiomerically enriched products with high enantiomeric excesses (ee = 82-99%). The results highlight the potential economic value of solid-state fermentation using agroindustrial side-stream feedstocks as an alternative to more expensive processes conducted in submerged fermentation.

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Section: Kinetic Resolution Of 1-phenylethyl Acetate (1)mentioning

confidence: 89%

Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation

et al. 2018

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“…A utilização de órgãos inteiros vegetais, sem qualquer preparação preliminar ou transformação, tem sido considerada (BRUNI et al, 2002;VANDENBERGHE et al, 2013). Esta metodologia oferece vantagens em termos de biodisponibilidade e economia de tempo, uma vez que não são necessárias etapas exigentes de preparação, extração, purificação e multiplicação do biocatalisador, promovendo assim a preservação de uma atividade catalítica máxima das enzimas (FONSECA et al, 2009;STRYJEWSKA et al, 2013).…”

Section: Introductionunclassified

Morus Nigra: Novo Biocatalisador Para Obtenção De Compostos De Interesse Industrial

Santos

Furlan

2020

BJD

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A síntese de compostos enantiomericamente puros é cada vez mais requisitada pelas indústrias farmacêutica, cosmética e agroalimentar, bem como está estabelecido a importância da quiralidade na atividade e propriedades biológicas de muitos compostos. Desta forma a biocatálise tornou-se uma alternativa viável na produção de compostos de interesse indústria. Assim o objetivo do presente estudo é avaliar as capacidades de biotransformação das folhas Morus nigra do terpenoide (+)-carvona, bem como determinar as condições biocatalíticas ideiais. Foram testadas as variáveis biomassa, concentração de substrato e pH do meio, sendo possível inferir que para todas as condições testadas as folhas de Morus nigra foram capazes de realizar hidrogenação do alceno ativado, bem como a redução da carbonila para álcool quiral. Estes resultados demonstram que a Morus nigra é uma potencial ferramenta biocatalítica para a obtenção de compostos de interesse industrial.

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“…Within the Green Chemistry methodologies, it's possible to emphasize the biocatalysis that can be defined in general as the use of enzymes, whole cells of microorganisms or plants (Vandenberghe et al, 2013). These enzymes sources are biocatalysts in organic synthesis, a very desirable use due to the attractive characteristics of biocatalysis, such as its high selectivity, which can be chemo, regio and stereoselective providing the reduction or elimination of the use of protective groups and simplifying separation processes that can be performed under mild conditions of temperature and pressure, with consequent reduction of costs and waste (Carvalho, 2011;Clouthier and Pelletier, 2012) Among the various biocatalytic reactions we can highlight the bioreductions of prochiral carbonyl groups, these reactions generate chiral alcohols, which are start materials widely used in the synthesis of drugs, flavorings, essences and agricultural products (Ni and Xu, 2012;Rowan, 2013).…”

Section: Introductionmentioning

confidence: 99%

Carrot Roots as Clean and Sustainable Biocatalyst for Obtaining Natural Menthol

2018

Aust. J. Basic & Appl. Sci.

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Bioreduction of Essential Oil of Mentha piperita L. (EOMP) After the determination of the ideal reaction conditions using the bioreduction of acetophenone as model, the reaction was anew performed following the parameters of test B. The EOMP, however, already presents menthol as the major compound, but with the reduction of the carbonyl monoterpenoids present in this essential oil it is possible to significantly raise the menthol content in the sample (Moghtader, 2013). Daucus carota used the ketone monoterpenoids as substrates and promoted the bioreduction of these selectively for the menthol compound. The data show that the bioreduction reaction mediated by carrot pieces is also effective in the presence of multiple molecules as in the case of EOMP. Essential oils represent value-added substances in the industrial sector due to their bioactive and technological potential, they also represent renewable sources to obtain molecules of interest. The molecular modification of these compounds by biocatalytic methods is an economically viable alternative that minimizes processes of purification and extraction. The data obtained in the present work show a further advantage of the use of Daucus carota as a source of biocatalyst with the ability to biotransform substrates directly from a matrix and the EOMP without prior purification in the medium of the unbuffered aqueous solution leading to a clean and sustainable of menthol. CONCLUSIONS In summary, this work proposes a modification in the traditional biocatalytic methodology, where the EOMP is used as a source of multiple substrates. Daucus carota was able to promote the bioreduction of the ketone monoterpenoids present in the EOMP leading to a menthol enrichment in the sample with high selectivity. Thus promoting a cleaner and more sustainable reaction to obtain a compound of great industrial interest.

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Enantioselective hydrolysis of racemic 1-phenylethyl acetate by an enzymatic system from fresh vegetables

Cited by 25 publications

References 21 publications

Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation

Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation

Morus Nigra: Novo Biocatalisador Para Obtenção De Compostos De Interesse Industrial

Carrot Roots as Clean and Sustainable Biocatalyst for Obtaining Natural Menthol

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