Partially purifiedCarica papayalipase: a versatile biocatalyst for the hydrolytic resolution of (R,S)-2-arylpropionic thioesters in water-saturated organic solvents

Ng, I-Son; Tsai, Shau Wei

doi:10.1002/bit.20492

Cited by 26 publications

(15 citation statements)

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“…Changing the chiral center substitution from an ethyl group to a pentyl group leads to an improved chiral recognition using CPL. Ng and Tsai (2005) proposed an active site model in which CPL has three enantioselective enzyme pockets with large, medium, and small pockets that can accommodate Profen's aryl, methyl, and hydrogen moieties, respectively. Thus, CPL enantioselectivity increases as the length of alkyl chain attached to the chiral carbon of (R,S)-2-methylalkanoic acids increases.…”

Section: Resultsmentioning

confidence: 99%

“…Excellent enantioselectivity was observed in water-saturated isooctane at 60°C (Cheng and Tsai 2004;Chen and Tsai 2005). The hydrolytic resolution of (R,S)-arylpropionic thioesters with CPL, was also investigated in water-saturated organic solvents (Ng and Tsai 2005). CPL-catalyzed transesterification between the 2,2,2-trifluoroethyl esters of N-benzyloxycarbonylated DL-amino acids carrying aliphatic side chains, and methanol, in cyclohexane produced an enantioselectivity in excess of 200 (Miyazawa et al 2005).…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective esterification of (R,S)-2-methylalkanoic acid with Carica papaya lipase in organic solvents

Chang

2011

Biotechnol Lett

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Isooctane was the best reaction medium for the enantioselective esterification of (R,S)-2-methylalkanoic acid with n-butanol using Carica papaya lipase as catalyst. Increasing linear alkyl-chain length of racemic 2-methylalkanoic acids from ethyl to hexyl increased the enantioselectivity (E) from 2.1 to 98.2 for the esterification of racemic 2-methylalkanoic acids with n-butanol at 35°C. Decreasing reaction temperature from 40 to 20°C increased the enantioselectivity (E) from 14 to 33 for the esterification of racemic 2-methylhexanoic acids with n-butanol. We obtained a maximum enantioselectivity, of E = 24.3, for the enantioselective esterification of racemic 2-methylhexanoic acids with n-butanol in isooctane at water activity 0.33, and at 35°C.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective esterification of (R,S)-2-methylalkanoic acid with Carica papaya lipase in organic solvents

Chang

2011

Biotechnol Lett

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“…A good potential of these microorganisms for producing chiral compounds was observed. 58 Thus, following these studies on enantioselective screening, the isolates selected in the synthetic reactions were used to mediate the resolution of the (R,S)-2-octanol reaction via transesterification with vinyl acetate (acyl donor). The values for the conversion percentages (%c), substrate and product enantiomeric excess (ee s and ee p ), and enantiomeric ratio (E) can be seen in Table 3.…”

Section: Resolution Of (Rs)-2-octanolmentioning

confidence: 99%

Potential application in biocatalysis of mycelium-bound lipases from Amazonian fungi

Zanotto¹,

Romano

Duvoisin

et al. 2009

J. Braz. Chem. Soc.

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Neste trabalho foram avaliados 212 fungos isolados de plantas da Região Amazônica quanto ao potencial de aplicação em biocatálise como fornecedores de lipases ligadas ao micélio. Estes isolados foram submetidos a ensaios de atividade hidrolítica e sintética. Quando submetidos ao ensaio com o substrato tributirina, 87% dos isolados apresentaram atividade hidrolítica. Destes, 30% mostraram bom crescimento em meio líquido indutor de lipase, e foram submetidos à avaliação sintética em reações de esterificação e transesterificação em solvente orgânico. Os nove fungos que apresentaram os melhores desempenhos sintéticos foram avaliados quanto a sua enantiosseletividade na reação de resolução do (R,S)-2-octanol. O isolado UEA_115 foi o biocatalisador mais versátil, apresentando bom desempenho nas reações de esterificação (conversão > 90%) e boa capacidade para a resolução do (R,S)-2-octanol (ee s 29%; ee p 99%; c 22%; E > 200). Com este estudo foi possível demonstrar o grande potencial dos fungos amazônicos como fornecedores de lipases para biocatálise.In this study, 212 fungi were isolated from Amazon region plants, aiming to obtain mycelium bound-lipase-producing biocatalysts. These isolates were submitted to hydrolytic and synthetic activity assays. When submitted to the tributyrine substrate test, 87% of the isolates showed hydrolytic activity. Of these, 30% showed good growth in lipase inducing liquid media and were submitted to evaluation of synthetic activity in esterification and transesterification reactions in organic solvents. The nine fungi which had the best synthetic activity were evaluated in the (R,S)-2-octanol resolution reaction, in order to verify the enantioselectivity of mycelium-bound lipases. The isolate UEA_115 was the most versatile biocatalyst, showing good performance in esterification reactions (conversion > 90%) and good ability for the resolution of (R,S)-2-octanol (ee s 29%; ee p 99%; c 22%; E > 200). Thus, this study has demonstrated the great potential of the Amazonian fungi as lipase suppliers for biocatalysts. Keywords: fungi, Amazon region, mycelium-bound lipase, biocatalyst screening, biocatalysis IntroductionIn recent years, global concern regarding the impact of human actions on the environment has been growing. The implementation of the concept of sustainable development in several productive activities has become an urgent issue. Fortunately, biotechnology also offers an increasing potential to meet the global demands for processes and products in greater harmony with the sustainability concept. 1,2 In this regard, one of the most promising tools in biotechnology is the field of applied biocatalysis, also referred to by some authors as biotransformation or enzymatic technology. 2,3 The advantages of using enzymes as biocatalysts in industrial processes have been shown to be ever more evident. Great versatility of catalyzed reactions, mild reaction conditions, and regio, chemo and enantioselective natures are those most frequently mentioned in the literature. 4 Such characteristic...

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“…La mayoría de los esfuerzos para llevar a cabo la purificación de estas proteínas se centran en la eliminación de las enzimas solubles en agua (principalmente proteasas), mediante diversos lavados con agua (Ng and Tsai, 2005;Rivera et al, 2012) y el empleo de detergentes como el NLS y CHAPS permite el aislamiento de una fracción de la actividad lipolítica presente en el látex de Carica papaya (Abdelkafi et al, 2009;Rivera et al, 2012).…”

Section: Introductionunclassified

Caracterización de diversas fracciones del látex Carica papaya como biocatalizadores en la hidrólisis de triglicéridos

Rivera¹,

Sandoval²

2014

Grasas y Aceites

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SUMMARY:Characterization of different lipolytic fractions in Carica papaya. Carica papaya latex contains interesting enzymes; the best known is papain, but lipolytic activity is also present. Due to the complexity of the latex polymeric matrix, it has not been possible to completely isolate enzymes responsible of lipolytic activity. The aim of this work was to characterize the lipolytic activity in the raw latex (CPLtx) and two partially purified fractions of papaya latex (without protease, CPL-p and without esterase CPL-e). Thermostability, optimal temperature and pH in the hydrolysis of two model triglycerides (tributyrin and triolein) and the selectivity towards triglycerides with different chain lengths were determined. The lipolytic activity of these biocatalysts in the hydrolysis of tributyrin and olive oil was similar to other commercially available immobilized microbial lipases (RM IM and Novozyme 435).KEYWORDS: Carica papaya; hydrolysis; latex; lipase; triglycerides RESUMEN: El látex de Carica papaya es fuente de interesantes enzimas, la más conocida es la papaína, pero la actividad lipolítica también está presente. No obstante, debido a la complejidad de la matriz polimérica del látex, hasta la fecha no ha sido posible aislar las enzimas responsables de la actividad lipolítica del látex. Este trabajo está dedicado a la caracterización de la actividad lipolítica en el látex crudo (CPLtx) y dos fracciones parcialmente purificadas de látex de papaya (sin proteasas, CPL-p y sin esterasas, CPL-e), a las cuales se determinaron la termostabilidad, temperatura y pH óptimos en la hidrólisis de dos triglicéridos modelo (tributirina y trioleina), así como la selectividad hacia triglicéridos con diferentes longitudes de cadena. Los tres presentaron actividades lipolíticas en hidrólisis de tributirina y aceite de oliva comparables con otras lipasas microbianas inmovilizadas disponibles comercialmente (RM IM y Novozyme 435). PALABRAS CLAVE: Carica papaya; hidrólisis; látex; lipasa; triglicéridosCitation/Cómo citar este artículo: Rivera I, Sandoval G. 2014. Caracterización de diversas fracciones del látex Carica papaya como biocatalizadores en la hidrólisis de triglicéridos. Grasas Aceites 65 (1): e003. doi: http://dx

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Partially purifiedCarica papayalipase: a versatile biocatalyst for the hydrolytic resolution of (R,S)-2-arylpropionic thioesters in water-saturated organic solvents

Cited by 26 publications

References 24 publications

Enantioselective esterification of (R,S)-2-methylalkanoic acid with Carica papaya lipase in organic solvents

Enantioselective esterification of (R,S)-2-methylalkanoic acid with Carica papaya lipase in organic solvents

Potential application in biocatalysis of mycelium-bound lipases from Amazonian fungi

Caracterización de diversas fracciones del látex <em>Carica papaya</em> como biocatalizadores en la hidrólisis de triglicéridos

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