Enantioselectivity of carbonic anhydrase catalyzed hydrolysis of mandelic methyl esters

1990 ◽  
Vol 68 (2) ◽  
pp. 314-316 ◽  
Author(s):  
Robert Chênevert ◽  
Martin Létourneau
Keyword(s):  
Carbonic Anhydrase ◽  
Methyl Esters ◽  
Enantiomeric Excess ◽  
Enantioselective Hydrolysis ◽  
Hydrolysis Of Esters ◽  
Hydrolysis Of

We report the first enantioselective hydrolysis of esters catalyzed by carbonic anhydrase. We found that mandelic methyl esters are good substrates for carbonic anhydrase. The R enantiomers are better substrates and enantiomeric excess values are moderate (40–51%). Keywords: carbonic anhydrase, mandelic esters, enantioselectivity, hydrolysis.

Isolation of an esterase-producing Trichosporon brassicae and its catalytic performance in kinetic resolution of ketoprofen

2001 ◽  
Vol 47 (12) ◽  
pp. 1101-1106 ◽  
Author(s):  
Duan Shen ◽  
Jian-He Xu ◽  
Peng-Fei Gong ◽  
Hui-Yuan Wu ◽  
You-Yan Liu
Keyword(s):  
Ethyl Ester ◽  
Sole Carbon Source ◽  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Catalytic Performance ◽  
Soil Samples ◽  
Enantioselective Hydrolysis ◽  
Resting Cells ◽  
Enantiomeric Ratio ◽  
Hydrolysis Of

A yeast strain CGMCC 0574, identified as Trichosporon brassicae, was selected from 92 strains for its high (S) selectivity in the hydrolysis of ketoprofen ethyl ester. The effective strains of the microorganisms were isolated from soil samples with the ester as the sole carbon source. The ethyl ester proved to be the best substrate for resolution of ketoprofen among several ketoprofen esters examined. The resting cells of CGMCC 0574 could catalyze the hydrolysis of ketoprofen ethyl ester with an enantiomeric ratio of 44.9, giving (S)-ketoprofen an enantiomeric excess of 91.5% at 42% conversion.Key words: ketoprofen, biocatalytic resolution, enantioselective hydrolysis, microbial esterase, Trichosporon brassicae.

Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters ofN-Protected Unusual Amino Acids

1989 ◽  
Vol 18 (12) ◽  
pp. 2219-2222 ◽  
Author(s):  
Toshifumi Miyazawa ◽  
Hitoshi Iwanaga ◽  
Shinichi Ueji ◽  
Takashi Yamada ◽  
Shigeru Kuwata
Keyword(s):  
Amino Acids ◽  
Pancreatic Lipase ◽  
Enantioselective Hydrolysis ◽  
Porcine Pancreatic Lipase ◽  
Unusual Amino Acids ◽  
Hydrolysis Of Esters ◽  
Hydrolysis Of

scholarly journals Cloning and Characterization of a Novel Esterase from Rhodococcus sp. for Highly Enantioselective Synthesis of a Chiral Cilastatin Precursor

2014 ◽  
Vol 80 (23) ◽  
pp. 7348-7355 ◽  
Author(s):  
Yan Zhang ◽  
Jiang Pan ◽  
Zheng-Jiao Luan ◽  
Guo-Chao Xu ◽  
Sunghoon Park ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Green Manufacturing ◽  
Enantioselective Hydrolysis ◽  
Content Type ◽  
Chiral Building Block ◽  
Chain Acyl ◽  
Novel Esterase ◽  
Optically Pure ◽  
Hydrolysis Of

ABSTRACTA novel nonheme chloroperoxidase (RhEst1), with promiscuous esterase activity for enantioselective hydrolysis of ethyl (S)-2,2-dimethylcyclopropanecarboxylate, was identified from a shotgun library ofRhodococcussp. strain ECU1013.RhEst1 was overexpressed inEscherichia coliBL21(DE3), purified to homogeneity, and functionally characterized. Fingerprinting analysis revealed thatRhEst1 preferspara-nitrophenyl (pNP) esters of short-chain acyl groups.pNP esters with a cyclic acyl moiety, especially that with a cyclobutanyl group, were also substrates forRhEst1. TheKmvalues for methyl 2,2-dimethylcyclopropanecarboxylate (DmCpCm) and ethyl 2,2-dimethylcyclopropane carboxylate (DmCpCe) were 0.25 and 0.43 mM, respectively.RhEst1 could serve as an efficient hydrolase for the bioproduction of optically pure (S)-2,2-dimethyl cyclopropane carboxylic acid (DmCpCa), which is an important chiral building block for cilastatin. As much as 0.5 M DmCpCe was enantioselectively hydrolyzed into (S)-DmCpCa, with a molar yield of 47.8% and an enantiomeric excess (ee) of 97.5%, indicating an extremely high enantioselectivity (E= 240) of this novel and unique biocatalyst for green manufacturing of highly valuable chiral chemicals.

Enantioselective hydrolysis of esters of secondary alcohols using lyophilized Bakers' yeast

1988 ◽  
Vol 10 (12) ◽  
pp. 744-749 ◽  
Author(s):  
B.I. Glänzer ◽  
K. Faber ◽  
H. Griengl ◽  
M. Röhr ◽  
W. Wöhrer
Keyword(s):  
Enantioselective Hydrolysis ◽  
Secondary Alcohols ◽  
Hydrolysis Of Esters ◽  
Hydrolysis Of

ChemInform Abstract: Selectivity in Carbonic Anhydrase Catalyzed Hydrolysis of Standard N- Acetyl-DL-amino Acid Methyl Esters.

ChemInform ◽  
2010 ◽  
Vol 24 (41) ◽  
pp. no-no
Author(s):  
R. CHENEVERT ◽  
R. BEL RHLID ◽  
M. LETOURNEAU ◽  
R. GAGNON ◽  
L. D'ASTOUS
Keyword(s):  
Amino Acid ◽  
Carbonic Anhydrase ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Hydrolysis Of ◽  
Amino Acid Methyl Esters

Hydrolysis of esters of oxy acids: pKa values for strong acids; Brønsted relationship for attack of water at methyl; free energies of hydrolysis of esters of oxy acids; and a linear relationship between free energy of hydrolysis and pKa holding over a range of 20 pK units

1978 ◽  
Vol 56 (17) ◽  
pp. 2342-2354 ◽  
Author(s):  
J. Peter Guthrie
Keyword(s):  
Rate Constants ◽  
Methyl Esters ◽  
Dimethyl Sulfate ◽  
Tetraethyl Orthosilicate ◽  
Free Energies ◽  
Dilute Aqueous Solution ◽  
Hydrolysis Of Esters ◽  
Strong Acids ◽  
Hydrolysis Of ◽  
Good Agreement

By combining various kinds of evidence from the literature it is possible to derive an internally consistent set of pKa values for the strong mineral acids and the arenesulfonic acids; the values are referred to dilute aqueous solution as standard state and are expected to be correct within 0.5 log unit. Using these pKa values and literature data for hydrolysis of methyl esters of acids of the type Y—XO3Men, where Y is O, OH, OMe, alkyl, or aryl and X is Cl, S, or P, a Brønsted plot can be constructed with slope equal to 1.02 ± 0.04. From the free energies of hydrolysis for dimethyl sulfate and the methyl phosphates it is possible to calculate rate constants for the microscopic reverse reaction. These define a Brønsted line of slope 0.27 ± 0.3, from which rate constants for the formation of the esters of perchloric and various sulfonic acids may be estimated. This permits calculation of free energies of hydrolysis for these esters.Thermochemical data in the literature permit calculation of the free energies of hydrolysis of dimethyl sulfate, trimethyl arsenite, and tetraethyl orthosilicate. In the case of dimethyl sulfate the calculation (using the previously reported eq. [1]) leads to a pKa value in close agreement with theoretical expectation, confirming that eq. [1] is valid for acids of pKa ≥ −3. For tetraethyl orthosilicate the thermochemical data are less precise but are in satisfactory agreement with the predictions of eq. [1]. The free energies of hydrolysis derived from the Brønsted correlations are also in good agreement with expectation based on eq. [1].For acids where resonance phenomena are important either in the acid itself (boric acid) or in the anion (nitric acid, nitrous acid, carboxylic acids) the experimental free energies of formation fall far from the line defined by eq. [1]. It is concluded that eq. [1] is limited to species where there is no n delocalization involving the reacting oxygen, but where this condition is satisfied, the equation holds over the entire accessible range of oxy acid pKa values, i.e., from −6.4 to 16.

scholarly journals Application of Lecitase® Ultra-Catalyzed Hydrolysis to the Kinetic Resolution of (E)-4-phenylbut-3-en-2-yl Esters

Catalysts ◽  
2018 ◽  
Vol 8 (10) ◽  
pp. 423 ◽  
Author(s):  
Aleksandra Leśniarek ◽  
Anna Chojnacka ◽  
Witold Gładkowski
Keyword(s):  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Optical Purity ◽  
Enantioselective Hydrolysis ◽  
Hydrolysis Of ◽  
Allyl Esters

The possibility of using Lecitase® Ultra as a novel alternative biocatalyst for the kinetic resolution of model racemic allyl esters of (E)-4-phenylbut-3-en-3-ol: Acetate (4a) and propionate (4b) through their enantioselective hydrolysis was investigated. Reaction afforded (+)-(R)-alcohol (3) and unreacted (−)-(S)-ester (4a or 4b). Hydrolysis of propionate 4b proceeded with higher enantioselectivity than acetate 4a. (R)-Alcohol (3) with highest enantiomeric excess (93–99%) was obtained at 20–30 °C by hydrolysis of propionate 4b, while the highest optical purity of unreacted substrate was observed for (S)-acetate 4a (ee = 34–56%). The highest enantioselectivity was found for the hydrolysis of propionate 4b catalyzed at 30 °C (E = 38). Reaction carried out at 40 °C significantly lowered enantiomeric excess of produced alcohol 3 and enantioselectivity in resolution. Lecitase® Ultra catalyzed the enantioselective hydrolysis of allyl esters 4a,b according to Kazlauskas’ rule to produce (R)-alcohol 3 and can find application as a novel biocatalyst in the processes of kinetic resolution of racemic allyl esters.

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