Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy

C E Humphrey, N J Turner, M A M Easson, S L Flitsch, R V Ulijn

Research output: Contribution to journalArticle

23 Citations (Scopus)

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.
LanguageEnglish
Pages13952-13953
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number46
Early online date25 Oct 2003
DOIs
Publication statusPublished - 19 Nov 2003

Fingerprint

Enzyme kinetics
Enantiomers
Lipases
Lipase
Hydrolysis
Resins
Kinetics
Acylation
Acids
Cyclohexane
3-phenylbutyric acid
Chromobacterium viscosum lipase

Keywords

  • lipase-catalyzed kinetic resolution
  • solid-phase
  • capture and release strategy

Cite this

Humphrey, C E ; Turner, N J ; Easson, M A M ; Flitsch, S L ; Ulijn, R V . / Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 46. pp. 13952-13953.
@article{cf7de33da54344728bce1424536aefcb,
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.",
keywords = "lipase-catalyzed kinetic resolution, solid-phase, capture and release strategy",
author = "Humphrey, {C E} and Turner, {N J} and Easson, {M A M} and Flitsch, {S L} and Ulijn, {R V}",
year = "2003",
month = "11",
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",

}

Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy. / Humphrey, C E ; Turner, N J ; Easson, M A M ; Flitsch, S L ; Ulijn, R V .

In: Journal of the American Chemical Society, Vol. 125, No. 46, 19.11.2003, p. 13952-13953.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy

AU - Humphrey, C E

AU - Turner, N J

AU - Easson, M A M

AU - Flitsch, S L

AU - Ulijn, R 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.

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.

KW - lipase-catalyzed kinetic resolution

KW - solid-phase

KW - capture and release strategy

U2 - 10.1021/ja037922x

DO - 10.1021/ja037922x

M3 - Article

VL - 125

SP - 13952

EP - 13953

JO - Journal of the American Chemical Society

T2 - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 46

ER -