Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy

Cara E. Humphrey; Nicholas J. Turner; Morag A M Easson; Sabine L. Flitsch; Rein V. Ulijn

doi:10.1021/ja037922x

Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy

Cara E. Humphrey, Nicholas J. Turner, Morag A M Easson, Sabine L. Flitsch, Rein V. Ulijn

Research output: Contribution to journal › Article › peer-review

Abstract

The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright © 2003 American Chemical Society.

Original language	English
Pages (from-to)	13952-13953
Number of pages	1
Journal	Journal of the American Chemical Society
Volume	125
Issue number	46
DOIs	https://doi.org/10.1021/ja037922x
Publication status	Published - 19 Nov 2003

Keywords

Carboxylic acids Role: BPN (Biosynthetic preparation), PUR (Purification or recovery), RCT (Reactant), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (chiral; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \"capture and release\" strategy using polyethyleneglycol-supported cyclohexanedione); Hydrolysis (enzymic, stereoselective; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \"capture and release\" strategy using polyethyleneglycol-supported cyclohexanedione); Resolution (kinetic; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \"capture and release\" strategy using polyethyleneglycol-supported cyclohexanedione); Solid phase synthesis (lipase-catalyzed kinetic resoln. of phenylbutyric acid via \"capture and release\" strategy using polyethyleneglycol-supported cyclohexanedione)

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10.1021/ja037922x

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@article{dbb8779b05024d50859909fdb5adbceb,

title = "Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a {"}Capture and Release{"} Strategy",

abstract = "The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright {\textcopyright} 2003 American Chemical Society.",

keywords = "Carboxylic acids Role: BPN (Biosynthetic preparation), PUR (Purification or recovery), RCT (Reactant), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (chiral; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \{"}capture and release\{"} strategy using polyethyleneglycol-supported cyclohexanedione); Hydrolysis (enzymic, stereoselective; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \{"}capture and release\{"} strategy using polyethyleneglycol-supported cyclohexanedione); Resolution (kinetic; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \{"}capture and release\{"} strategy using polyethyleneglycol-supported cyclohexanedione); Solid phase synthesis (lipase-catalyzed kinetic resoln. of phenylbutyric acid via \{"}capture and release\{"} strategy using polyethyleneglycol-supported cyclohexanedione)",

author = "Humphrey, {Cara E.} and Turner, {Nicholas J.} and Easson, {Morag A M} and Flitsch, {Sabine L.} and Ulijn, {Rein V.}",

year = "2003",

month = nov,

day = "19",

doi = "10.1021/ja037922x",

language = "English",

volume = "125",

pages = "13952--13953",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "46",

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TY - JOUR

T1 - Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy

AU - Humphrey, Cara E.

AU - Turner, Nicholas J.

AU - Easson, Morag A M

AU - Flitsch, Sabine L.

AU - Ulijn, Rein V.

PY - 2003/11/19

Y1 - 2003/11/19

N2 - The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright © 2003 American Chemical Society.

AB - The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright © 2003 American Chemical Society.

KW - Carboxylic acids Role: BPN (Biosynthetic preparation), PUR (Purification or recovery), RCT (Reactant), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (chiral; lipase-catalyzed kinetic resoln. of phenylbutyric acid via \"capture an

U2 - 10.1021/ja037922x

DO - 10.1021/ja037922x

M3 - Article

SN - 0002-7863

VL - 125

SP - 13952

EP - 13953

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 46

ER -

Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy

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Keywords

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