Ionic liquids: efficient additives for Candida rugosa lipase-catalysed enantioselective hydrolysis of butyl 2-(4-chlorophenoxy)propionate

Mohile, Swapnil S; Potdar, Mahesh Kamalakar; Harjani, Jitendra R.; Nara, Susheel J.; Salunkhe, Manikrao M.

doi:10.1016/j.molcatb.2004.05.002

Cited by 41 publications

(15 citation statements)

References 25 publications

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“…With increased substrate concentration from 10 mmol L −1 to 60 mmol L −1 STY was increased by a factor of 1.7. Enantioselectivity of the hydrolysis of butyl 2-(4-chlorophenoxy) propionate catalysed by the Candida rugosa lipase could be increased by the addition of IL to an aqueous buffer solution (Mohile et al 2004). Increasing the IL to 50% (v/v) raised the ee from 47% to >99%.…”

Section: Introductionmentioning

confidence: 99%

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Ionic liquids in biotechnology: applications and perspectives for biotransformations

Roosen

Müller

Greiner

2008

Appl Microbiol Biotechnol

163

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Ionic liquids are considered as an alternative to organic solvents for catalysis. The literature in this field is reviewed with focus on advantageous use of ionic liquids in biocatalysis and biotransformations. The overview reveals that the exploration and mapping of ionic liquids with respect to biocatalysis is still sketchy. It is apparent that advantages can be gained in view of activity, stability and selectivity. Furthermore, integration of reaction and separation has a high potential in the field. The review presents quantitative data on the productivities, space-time yields, as well as stability as far as they can be extracted from the literature.

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Section: Introductionmentioning

confidence: 99%

“…The hydrolysis of 3,4,6-tri-O-acetyl-D-glucal catalysed by celite-supported Pseudomonas cepacia lipase was compared for the biphasic mixtures of buffer and [BMIM] [PF 6 ] or [BMIM] [BF 4 ] and monophasic THF/buffer (Mohile et al 2004). The regioselectivity was improved to 98% from 62% with comparable productivities for THF and…”

Section: Introductionmentioning

confidence: 99%

Ionic liquids in biotechnology: applications and perspectives for biotransformations

Roosen

Müller

Greiner

2008

Appl Microbiol Biotechnol

163

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“…Our group investigated CRL catalyzed enantioselective hydrolysis of butyl-2-(4-chlorophenoxy)propionate in an aqueous buffer with IL as a co-solvent (Scheme 4) [27]. The markedly enhanced enantioselectivity towards the R-enantiomer of the substrate was observed under the optimal additive conditions (1:1, IL and buffer 4 ].…”

Section: Enzyme Mediated Enantioselective Reactions In Ionic Liquidsmentioning

confidence: 99%

Enzyme Mediated Reactions in Ionic Liquids

Harjani¹,

Naik²,

Nara³

et al. 2007

COS

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“…In general, low enantioselectivity for crude Candida rugosa lipases (CRL), moderate to high enantioselectivity but with low reactivity for Carica papaya lipase (CPL) were reported. [10][11][12] Many efforts have been made to improve CRL activity and enantioselectivity, for example, use of purified or isopropanol (IPA)-treated lipase, [13][14][15][16][17][18] addition of dimethyl sulfoxide (DMSO), carbon tetrachloride, or benzene, 17,[19][20][21] ionic liquids as the reaction medium, 22 and organosilicon alcohols as the acyl acceptor. 11,12,23 Nevertheless, considerations of solvent toxicity, biocatalyst recycle and downstream separation capability, and cost effective-ness because of low reactivity have hindered such methods practicably used in industry.…”

Section: Introductionmentioning

confidence: 99%

(R,S)‐2‐chlorophenoxyl pyrazolides as novel substrates for improving lipase‐catalyzed hydrolytic resolution

Kao

et al. 2011

Chirality

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The best reaction condition of Candida antartica lipase B as biocatalyst, 3-(2-pyridyl)pyrazole as leaving azole, and water-saturated methyl t-butyl ether as reaction medium at 45°C were first selected for performing the hydrolytic resolution of (R,S)-2-(4-chlorophenoxyl) azolides (1-4). In comparison with the kinetic resolution of (R,S)-2-phenylpropionyl 3-(2-pyridyl)pyrazolide or (R,S)-α-methoxyphenylacetyl 3-(2-pyridyl)pyrazolide at the same reaction condition, excellent enantioselectivity with more than two order-of-magnitudes higher activity for each enantiomer was obtained. The resolution was then extended to other (R,S)-3-(2-pyridyl)pyrazolides (5-7) containing 2-chloro, 3-chloro, or 2,4-dichloro substituent, giving good (E > 48) to excellent (E > 100) enantioselectivity. The thermodynamic analysis for 1, 2, and 4-7 demonstrates profound effects of the acyl or leaving moiety on varying enthalpic and entropic contributions to the difference of Gibbs free energies. A thorough kinetic analysis further indicates that on the basis of 6, the excellent enantiomeric ratio for 4 and 7 is due to the higher reactivity of (S)-4 and lower reactivity of (R)-7, respectively.

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Ionic liquids: efficient additives for Candida rugosa lipase-catalysed enantioselective hydrolysis of butyl 2-(4-chlorophenoxy)propionate

Cited by 41 publications

References 25 publications

Ionic liquids in biotechnology: applications and perspectives for biotransformations

Ionic liquids in biotechnology: applications and perspectives for biotransformations

Enzyme Mediated Reactions in Ionic Liquids

(R,S)‐2‐chlorophenoxyl pyrazolides as novel substrates for improving lipase‐catalyzed hydrolytic resolution

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