Dimethyl sulfoxide as a co-solvent dramatically enhances the enantioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives

Watanabe, Keita; Ueji, Shinichi

doi:10.1039/b100182p

Cited by 38 publications

(23 citation statements)

References 32 publications

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“…[33] It is a complex phenomenon and has been attributed to conformational changes in the biocatalyst but also to an improved solubility of the substrate [33] and hence the effect is difficult to predict. In some cases, adding [23,30] or changing a cosolvent [34] could lead to dramatic changes (even inversion) in the enantioselectivity.…”

Section: Activity Of the Enzymesmentioning

confidence: 98%

“…This phenomenon has also been observed before with lipases in the kinetic resolution of secondary alcohols. [29,30] Furthermore, the effect could arise from differences in the interaction of the nitrogen atom of the pyridine ring with residues or water molecules in the active site of enzymes. Zhu et al [31] observed this kind of effect in the reduction of aryl ketones with ketoreductases.…”

Section: Activity Of the Enzymesmentioning

confidence: 99%

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An Enzymatic Toolbox for the Kinetic Resolution of 2‐(Pyridin‐x‐yl)but‐3‐yn‐2‐ols and Tertiary Cyanohydrins

et al. 2010

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The kinetic resolution of a series of acetates of tertiary alcohols bearing a nitrogen substituent has been studied by using several recombinant carboxyl esterases and variants thereof expressed in E. coli. Most of the enzymes were active in the conversion of these tertiary alcohols and excellent enantioselectivities were achieved in the synthesis of three 2-(pyridin-x-yl)but-3-yn-2-ols with the nitrogen atom in the pyridine ring in the 2Ј-, 3Ј-, and 4Ј-positions. The resolution

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Section: Activity Of the Enzymesmentioning

confidence: 98%

Section: Activity Of the Enzymesmentioning

confidence: 99%

An Enzymatic Toolbox for the Kinetic Resolution of 2‐(Pyridin‐x‐yl)but‐3‐yn‐2‐ols and Tertiary Cyanohydrins

et al. 2010

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“…Owing to the preliminary nature of this study, we began our work selecting DMSO and IPA according to published data regarding enzyme activation. 13,14 In particular, we directed our attention to the influence that the substituent at the stereogenic centre could exert upon the different enzymatic chiral recognition in the different media employed.…”

Section: Introductionmentioning

confidence: 99%

Candida rugosa lipase‐catalysed kinetic resolution of 2‐substituted‐aryloxyacetic esters with dimethylsulfoxide and isopropanol as additives

Ammazzalorso¹,

Amoroso²,

Bettoni³

et al. 2007

Chirality

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Candida rugosa lipase-catalysed hydrolysis of three different 2-substituted-aryloxyacetic esters was performed in aqueous buffer containing dimethyl sulphoxide and isopropanol from 0 to 80% v/v as additives, in order to obtain an enhancement of the enantioselectivity. For 2-(p-chlorophenoxy)acetic acid and 2-n-butyl-2-(p-chlorophenoxy)acetic acid ethyl esters, DMSO enhanced enzyme enantioselectivity more than IPA with an opposite enzymatic enantiopreference. The cosolvents moderately improved Candida rugosa lipase enantioselectivity for 2-phenyl-2-(p-chlorophenoxy)acetic acid ethyl ester.

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“…[20,24] The lipase has a rather wide active site and the ability to tolerate high concentrations of organic co-solvents. [25][26][27] The hydrolysis of glucose pentaacetate has been investigated at different pH by several authors. [20,23,24] Reactions at pH 4-5 using CRL led to high regioselectivity favouring hydrolysis at C-6, whereas at methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside substrate inhibition were observed, which in part could be overcome by increasing the reaction volume.…”

Section: Introductionmentioning

confidence: 99%

Regioselective C‐6 Hydrolysis of MethylO‐Benzoyl‐pyranosides Catalysed byCandida RugosaLipase

Esmurziev

Sundby²,

Hoff

2009

Eur J Org Chem

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Hydrolysis of six methyl O‐benzoyl‐pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C‐6. The rate of reaction was dependent on pyranoside structure, reaction temperature and scale, dioxane concentration and agitation speed. Starting from their C‐6 O‐benzoyl precursors, the methyl 2,3,4‐tri‐O‐benzoyl‐pyranosides of α‐D‐galactose, β‐D‐galactose, α‐D‐glucose, and methyl 2,3‐di‐O‐benzoyl‐α‐D‐galactopyranoside could be isolated in 85–96 % yield. In hydrolysis of methyl 2,3,4,6‐tetra‐O‐benzoyl‐α‐D‐glucopyranoside and methyl 2,3,4,6‐tetra‐O‐benzoyl‐β‐D‐galactopyranoside substrate inhibition were observed, which in part could be overcome by increasing the reaction volume. Methyl 2,3,4,6‐tetra‐O‐benzoyl‐β‐D‐glucopyranoside and methyl 2,3,4,6‐tetra‐O‐benzoyl‐α‐D‐mannopyranoside were poor substrates for Candida rugosa lipase and low degree of conversion towards products were obtained under all conditions. No acyl migration was detected in any of the products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Dimethyl sulfoxide as a co-solvent dramatically enhances the enantioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives

Cited by 38 publications

References 32 publications

An Enzymatic Toolbox for the Kinetic Resolution of 2‐(Pyridin‐x‐yl)but‐3‐yn‐2‐ols and Tertiary Cyanohydrins

An Enzymatic Toolbox for the Kinetic Resolution of 2‐(Pyridin‐x‐yl)but‐3‐yn‐2‐ols and Tertiary Cyanohydrins

Candida rugosa lipase‐catalysed kinetic resolution of 2‐substituted‐aryloxyacetic esters with dimethylsulfoxide and isopropanol as additives

Regioselective C‐6 Hydrolysis of MethylO‐Benzoyl‐pyranosides Catalysed byCandida RugosaLipase

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