Kinetic Resolution of Enantiomers in Racemic and Enantiomerically Enriched 2-Alkanols by &lt;i&gt;Pseudomonas cepacia&lt;/i&gt; Lipase Catalyzed Transesterification with Isopropenyl Acetate in Organic Solvent

Kanamori, Yoshimi; Watanabe, Michitoshi; Kawauchi, Keiyo; Chen, Yun-Gang; Yanagishita, Hiroshi; Hirata, Hirofumi

doi:10.5650/jos.54.21

J. Oleo Sci.

2005

DOI: 10.5650/jos.54.21

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Kinetic Resolution of Enantiomers in Racemic and Enantiomerically Enriched 2-Alkanols by <i>Pseudomonas cepacia</i> Lipase Catalyzed Transesterification with Isopropenyl Acetate in Organic Solvent

Yoshimi Kanamori

Michitoshi Watanabe

Keiyo Kawauchi

et al.

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Cited by 5 publications

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“… a See ref . b The reaction was run at 0 °C in chloroform. c Reactions were concentrated by rotary evaporator to remove excess methanol, and solvent was added prior to the kinetic resolution. …”

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Obtaining Enriched Compounds via a Tandem Enantioselective Reaction and Kinetic Resolution Polishing Sequence

2012

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Herein we describe a tandem method of coupling an enantioselective reaction with a nonenzymatic kinetic resolution to prepare highly enantioenriched compounds. The procedure employs a moderately selective enantioselective reaction on a ketone or aldehyde to form an enriched alcohol followed by a kinetic resolution of the alcohol to generate ee's of >99% in yields greater than what is possible with a kinetic resolution. This method highlights an avenue to quickly acquire highly enriched compounds without developing and optimizing a new methodology.

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Obtaining Enriched Compounds via a Tandem Enantioselective Reaction and Kinetic Resolution Polishing Sequence

2012

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“…Enantiomerically pure 2-alkanols [(R)-(1) (ee 99%) and (S)-(1) (ee 99%); 2-heptanol (72-OH), 2-octanol (82-OH), 2-nonanol (92-OH), 2-decanol (102-OH), 2-undecanol (112-OH) and 2-dodecanol (122-OH)] were the stocked samples prepared by repeating the acetylation (transesterification) with VA or isopropenyl acetate (IPA) in 1,2-dichloroethane 10,11) . Organic solvents [hexane (Hex), cyclohexane (c-Hex), toluene (Tol), benzene (PhH), diisopropyl ether (IPE), tetrahydrofuran (THF), acetone (DMK), acetonitrile (MCN), 1,4-dioxane (DO) and 1,2-dichloroethane (DCE)] were purified by the ordinary method 12) .…”

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Kinetic Studies on Lipase-Catalyzed Acetylation of 2-Alkanol with Vinyl Acetate in Organic Solvent

et al. 2007

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OH], and different organic solvents ( ) in order to clarify the second order rate constants for (R)-(1) and (S)-(1), and the enantioselectivity which are affected by solvent 309Correspondence to: Hirofumi Hirata, Department of Bioscience and Technology, School of Engineering, Hokkaido Tokai University, 5-1 Minamisawa, Minami-ku, Sapporo 005-8601, JAPAN E-mail: hirata@db.htokai.ac.jp Accepted February 26, 2007 (received for review December 7, 2006 Journal of Oleo Science Copyright ©2007 by Japan Oil Chemists ' Society J. Oleo Sci. 56,(6) 309-317 (2007) Abstract: Lipase-catalyzed acetylation of 2-alkanol with vinyl acetate has been studied kinetically using Burkholderia cepacia lipase (BCL), enantiomerically pure (R)-and (S)-2-alkanols and different organic solvents. The rate equation was derived by the steady state method for the simplified mechanism. The second order rate constants (k R and k S ) for (R)-and (S)-2-alkanols were evaluated from the slopes of the double reciprocal plots, v -1 vs. [2-alkanol] -1 , where v is the initial rate of the reaction. The log k R value increased with the solvent hydrophobicity log P, where P is a partition coefficient of a given solvent between octanol and water. The log k S value also increased with log P except the bulky solvents such as 1,4-dioxane and cyclohexane, in which the rates were faster than those expected from the log k S vs. log P plot. The slope of log k S vs. log P plot was larger than that for (R)-2-alkanol. Thus, log E (E=k R /k S : enantioselectivity) decreased with log P except the bulky solvents. The rate constants and the enantioselectivity were different depending on the structure (carbon number CN) of 2-alkanol. The log E vs. CN plot was minimized at CN=8 and 10 and the log k S vs. CN plot maximized at CN=8 and 10. In contrast the log k R vs. CN plot showed a different feature from the log E vs. CN plot. These facts suggest that dependence of E on CN is more strongly affected by the reactivity of (S)-2-alkanol than that of (R) isomer in this acetylation. Kinetic Studies on Lipase-Catalyzed Acetylation of 2-Alkanol with Vinyl Acetate in Organic Solvent

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Identification of a novel esterase from the thermophilic bacterium Geobacillus thermodenitrificans NG80-2

et al. 2019

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Kinetic Resolution of Enantiomers in Racemic and Enantiomerically Enriched 2-Alkanols by <i>Pseudomonas cepacia</i> Lipase Catalyzed Transesterification with Isopropenyl Acetate in Organic Solvent

Cited by 5 publications

References 28 publications

Obtaining Enriched Compounds via a Tandem Enantioselective Reaction and Kinetic Resolution Polishing Sequence

Obtaining Enriched Compounds via a Tandem Enantioselective Reaction and Kinetic Resolution Polishing Sequence

Kinetic Studies on Lipase-Catalyzed Acetylation of 2-Alkanol with Vinyl Acetate in Organic Solvent

Identification of a novel esterase from the thermophilic bacterium Geobacillus thermodenitrificans NG80-2

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