Potential application of native lipases in the resolution of (RS) - phenylethylamine

Abstract

O desempenho de duas lipases nativas (lipase de Aspergillus niger e Rhizopus oligosporus), e a influência da temperatura, doador acila (acetato de etila, acetato de vinila, acetato de iso-propenila e anidrido acético) e do meio orgânico foi avaliado na resolução da (RS)-feniletilamina (1). O efeito de anions em uma série de líquidos iônicos (LIs) baseados em derivados do imidazol [BMIm][X], onde X = BF 4 , PF 6 , SCN e Cl em n-heptano e acetato de vinila, também foi verificado com a lipase nativa de A. niger. Com esta lipase, a amida R-2b foi obtida com conversões de 6 até > 99% e valores de E de 2 até > 200, em n-heptano ou n-hexano. Os maiores valores de E obtidos, usando sistema bifásico formado por n-heptano e [BMIm][ PF 6 ] ou [BMIm][ BF 4 ] 9:1 (v/v), foram de 9 e 7, respectivamente, quando comparado com o solvente puro (E = 2). A influência dos ânions segue a seguinte ordem: PF 6->BF 4-> SCN-> Cl-. The performance of two native lipases (lipase from Aspergillus niger and Rhizoupus oligosporus) in the resolution of (RS)-phenylethylamine (1), varying the temperature, acyl donor type (ethyl acetate, vinyl acetate, iso-propenyl acetate and acetic anhydride) and organic medium, was studied. The effect of the nature of the anion using native A. niger lipase in n-heptane with a series of imidazolium-based ILs [BMIm][X], where X = BF 4 , PF 6 , SCN and Cl, was also evaluated. Using the lipase from A. niger, the R-2b amide was obtained with conversions from 6 to > 99% and E-values from 2 to > 200, with n-heptane or n-hexane. This lipase showed better E-values in a two-phase system using n-heptane and [BMIm][PF 6 ] or [BMIm][BF 4 ] 9:1 (v/v), obtaining values of 9 and 7, respectively, when vinyl acetate was used as the acyl donor, compared to the use of pure n-heptane (E = 2). The series for the anions in terms of decreasing performance was as follows: PF 6->BF 4-> SCN-> Cl- .

The influence of conventional heating and microwave irradiation on the resolution of (RS)-sec-butylamine catalyzed by free or immobilized lipases

“…This lipase has previously been used for the resolution of ibuprofen 29 and (RS)-phenylethylamine. 39 The potential of this biocatalyst for industrial use has also been described recently. 5 Thus, In the next study, the type and relative amount of acyl donor were evaluated for the resolution of (RS)-1 using free A. niger lipase as the biocatalyst.…”

The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases

“…Basically, the interest in using ionic liquids in biocatalysis is the desire to replace volatile organic solvents by non-volatile ionic liquids. 33,34 To 6 ] can be explained considering that this ionic liquid is considered more apolar, and thus, more suitable for use in enzymatic catalysis. 23,34,35 A comparison of the use of the ILs as co-solvents with the use of toluene showed that the reactions presented higher degrees of conversion and ee s values in the presence of the pure organic solvent.…”

Chemo-enzymatic epoxidation of -caryophyllene mediated lipases and by mycelium-bound lipases

“…1,2 In this study, twelve commercial lipases from different sources, that is, Candida antarctica B (CAL-B, 10,000 PLU/g); Burkholderia cepacia (PS-C Amano ® I, 1.638 U/g); PS Amano ® SD; 30,000 U/g; PS Amano ® , 30,000 U/g; PS Amano ® IM, 500u/g; PS-C Amano ® II, 1,000 U/g; Rhizopus oryzae (150 u/mg); Candida rugosa (30,000 u/g); Pseudomonas fluorescens (26,600 U/g); Aspergillus niger (120,000 u/g); Rhizomucor miehei (5-6 BAUN/g); and Mucor miehei (5-6 BAUN/g), were used in the chemoenzymatic epoxidation of caryophyllene (0.6 mL, 2.5 mmol) using aqueous hydrogen peroxide (1.2 mL, 30%) as the oxidant agent and octanoic acid (0.16 mL, 1 mmol) as the acyl donor in dichloromethane at ~25°C. Also, two native lipases from A. niger (LAN 18.2 U/mL) and Rhizopus oligosporus, (LRO 14.9 U/mL) isolated from microorganisms of a soil from the Bueno Brandão region (MG, Brazil) 3 , and nine mycelium-bound lipases from Amazon region fungi (UEA_01, UEA_06, UEA_07, UEA_23, UEA_27, UEA_28, UEA_41, UEA_53 and UEA_115) 4 , were screened in this study (Scheme 1). Scheme 1 Chemo-enzymatic epoxidation of caryophyllene…”