Microwave-Assisted Resolution of α-Lipoic Acid Catalyzed by  an Ionic Liquid Co-Lyophilized Lipase

Liu, Ning; Wang, Lei; Wang, Zhi; Jiang, Liyan; Wu, Zhuofu; Yang, Hong; Xie, Xiaoguang

doi:10.3390/molecules20069949

Cited by 9 publications

(5 citation statements)

References 41 publications

(52 reference statements)

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“…The reaction mixture consisted of isopropanol and n-heptane (6:4) to which 100 µl of racemic sotalol solution (2.5 mg/ml in methanol) was added. Then 10 mg/ml of lipase AP6 was added to the reaction mixture to start the reaction [28][29][30] . The flask containing this reaction mixture was sealed and incubated at 25° for 36 h in a refrigerated shaker incubator at 120 rpm.…”

Section: Free-lipase Ap6 Enzyme Catalysed Enantioselective Resolution Of Sotalolmentioning

confidence: 99%

Enantioselective Conversion of Racemic Sotalol to R(-)-Sotalol by Lipase AP6

Swetha¹,

Vijitha²,

Veeresham³

2018

pharmaceutical-sciences

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Most pharmaceutical compounds have asymmetric nature and are optically active. Compounds with one asymmetric centre (chiral centre) would exhibit two enantiomeric forms and among them one is pharmacologically active (eutomer) while the other one contributed side effects or toxic effects or totally inert (distomer) [1] . Hence, current interest is towards development and administration of eutomer instead of its racemic mixture to improve therapeutic efficacy and reduce the unwanted effects due to the distomer [2] . Biocatalysts have excellent selectivity under mild reaction conditions [2] and hence in this study various whole-cell microorganisms like Bacillus subtilis [3] , Escherichia coli [4] , Pseudomonas putida [5] , Sphingomonas paucimobilis [6] , Rhodococcus erythropolis [7] , Streptomyces halstedii [8] , Aspergillus niger [9] , Candida parapsilosis [10] , Geotrichum candida [11] , Rhizopus oryzae [12] , Cunninghamella elegans [13] and Cunninghamella blakesleeana [14] were employed as biocatalysts for the stereo inversion of racemic sotalol to its active enantiomer. However, a limitation for using whole-cell microorganisms as biocatalysts is reduced stereo selectivity due to competition between multiple enzymes of the microorganism for the same substrate [15] . The use of isolated pure enzymes with suitable cofactors as biocatalysts would help overcome this limitation of using whole-cell microorganisms [16] and the reactions catalysed by pure enzymes also serves some other advantages like they are highly selective under mild conditions, more catalytic in nature and environmentally benign [2] . Lipases have great versatility in catalysing different reactions like aminolysis, esterification, transesterification and interesterification. The means followed by lipases to catalyse these reactions can be described as a ping-pong bi-bi mechanism. Accordingly, first step involves nucleophilic attack on the carbonyl group of a drug, which results in acyl-

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Section: Free-lipase Ap6 Enzyme Catalysed Enantioselective Resolution Of Sotalolmentioning

confidence: 99%

Enantioselective Conversion of Racemic Sotalol to R(-)-Sotalol by Lipase AP6

Swetha¹,

Vijitha²,

Veeresham³

2018

pharmaceutical-sciences

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“…The material absorbed microwave energy to facilitate the destruction of the cellular structure and release of active substance out of plant cell. In addition, microwave irradiation could improve enzyme performance, which was detailed in reference [32]. Therefore, microwave irradiation at 500 W for 10 min was selected as the optimal pretreatment method in four alternative offers.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Hydrolysis and Simultaneous Extraction for Preparation of Genipin from Bark of Eucommia ulmoides after Ultrasound, Microwave Pretreatment

Guo

Zhao

et al. 2015

Molecules

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A continuous process based on the combination of ultrasounds and/or microwaves pretreatments followed by enzymatic hydrolysis and simultaneous extraction (EHSE) has been proposed to recover genipin from Eucommia ulmoides bark. At first, in the pretreatment step, the mixture of 1.0 g dried bark powder and 10 mL deionized water were irradiated by microwave under 500 W for 10 min. Then, in hydrolysis step, the optimal conditions were as follows: 0.5 mg/mL of cellulase concentration, 4.0 pH of enzyme solution, 24 h of incubation time and 40 °C of incubation temperature. After incubation, 10 mL ethanol was added to extract genipin for 30 min by ultrasound. After EHSE treatment, the yield of genipin could reach 1.71 μmol/g. Moreover, scanning electron micrographs illustrated that severe structural disruption of plant was obtained by EHSE. The results indicated that the EHSE method provided a good alternative for the preparation of genipin from Eucommia ulmoides bark as well as other herbs.

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“…32 In 2015, Liu et al combined an ionic liquid co-lyophilized lipase with microwave irradiation to improve enzyme performance in the enantioselective esterification of ALA . 33 Under optimal reaction conditions, the ionic liquid co-lyophilized lipase exhibited satisfactory enzyme performance ( E value, 41.2; enzyme activity, 178.1 μmol h −1 mg −1 ).…”

Section: Synthesis Of R-alamentioning

confidence: 94%

“… 31 The enzyme shows enantioselectivity towards the S -ALA (72% ee). In 2009, Yan et al reported that the lipase from Aspergillus oryzae WZ007 is another potential candidate for enzymatic resolution of ALA. 32 In 2015, Liu et al combined an ionic liquid co-lyophilized lipase with microwave irradiation to improve enzyme performance in the enantioselective esterification of ALA. 33 Under optimal reaction conditions, the ionic liquid co-lyophilized lipase exhibited satisfactory enzyme performance ( E value, 41.2; enzyme activity, 178.1 μmol h −1 mg −1 ).…”

Section: Synthesis Of R -Alamentioning

confidence: 94%