Effects of Carica papaya lipase pretreatments on enantioselective hydrolysis of (R,S)-arylpropionic thioesters

I. Son Ng, Shau Wei Tsai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The hydrolytic resolution of (R,S)-naproxen 2,2,2-trifluoroethyl thioester in water-saturated isooctane was employed as a model system to study the pretreatment effect of Carica papaya lipase on the enzyme performance. In comparison with the result of using deionized water in the pretreatment, improvements in lipase activity and enantioselectivity were achieved when polar organic solvents, pH 8 phosphate buffer, or aqueous solution containing methyl-β-cyclodextrin, but not NaCl or 18-crown-6, was employed. The lipase pretreated with isopropyl ether was selected as the best lipase and further employed to resolve 2,2,2-trifluroethyl thioesters of (R,S)-fenoprofen, (R,S)-flurbiprofen and (R,S)-ibuprofen.

Original languageEnglish
Pages (from-to)331-337
Number of pages7
JournalJournal of the Chinese Institute of Chemical Engineers
Volume36
Issue number4
Publication statusPublished - 2005 Jul

Fingerprint

Lipases
Lipase
Hydrolysis
Fenoprofen
Flurbiprofen
Deionized water
Enantioselectivity
Ibuprofen
Cyclodextrins
Organic solvents
Ethers
Buffers
Phosphates
Enzymes
Water

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

@article{89cc9ca0622443afa975f80422d3803e,
title = "Effects of Carica papaya lipase pretreatments on enantioselective hydrolysis of (R,S)-arylpropionic thioesters",
abstract = "The hydrolytic resolution of (R,S)-naproxen 2,2,2-trifluoroethyl thioester in water-saturated isooctane was employed as a model system to study the pretreatment effect of Carica papaya lipase on the enzyme performance. In comparison with the result of using deionized water in the pretreatment, improvements in lipase activity and enantioselectivity were achieved when polar organic solvents, pH 8 phosphate buffer, or aqueous solution containing methyl-β-cyclodextrin, but not NaCl or 18-crown-6, was employed. The lipase pretreated with isopropyl ether was selected as the best lipase and further employed to resolve 2,2,2-trifluroethyl thioesters of (R,S)-fenoprofen, (R,S)-flurbiprofen and (R,S)-ibuprofen.",
author = "Ng, {I. Son} and Tsai, {Shau Wei}",
year = "2005",
month = "7",
language = "English",
volume = "36",
pages = "331--337",
journal = "Journal of the Taiwan Institute of Chemical Engineers",
issn = "1876-1070",
publisher = "Taiwan Institute of Chemical Engineers",
number = "4",

}

TY - JOUR

T1 - Effects of Carica papaya lipase pretreatments on enantioselective hydrolysis of (R,S)-arylpropionic thioesters

AU - Ng, I. Son

AU - Tsai, Shau Wei

PY - 2005/7

Y1 - 2005/7

N2 - The hydrolytic resolution of (R,S)-naproxen 2,2,2-trifluoroethyl thioester in water-saturated isooctane was employed as a model system to study the pretreatment effect of Carica papaya lipase on the enzyme performance. In comparison with the result of using deionized water in the pretreatment, improvements in lipase activity and enantioselectivity were achieved when polar organic solvents, pH 8 phosphate buffer, or aqueous solution containing methyl-β-cyclodextrin, but not NaCl or 18-crown-6, was employed. The lipase pretreated with isopropyl ether was selected as the best lipase and further employed to resolve 2,2,2-trifluroethyl thioesters of (R,S)-fenoprofen, (R,S)-flurbiprofen and (R,S)-ibuprofen.

AB - The hydrolytic resolution of (R,S)-naproxen 2,2,2-trifluoroethyl thioester in water-saturated isooctane was employed as a model system to study the pretreatment effect of Carica papaya lipase on the enzyme performance. In comparison with the result of using deionized water in the pretreatment, improvements in lipase activity and enantioselectivity were achieved when polar organic solvents, pH 8 phosphate buffer, or aqueous solution containing methyl-β-cyclodextrin, but not NaCl or 18-crown-6, was employed. The lipase pretreated with isopropyl ether was selected as the best lipase and further employed to resolve 2,2,2-trifluroethyl thioesters of (R,S)-fenoprofen, (R,S)-flurbiprofen and (R,S)-ibuprofen.

UR - http://www.scopus.com/inward/record.url?scp=25144496065&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=25144496065&partnerID=8YFLogxK

M3 - Article

VL - 36

SP - 331

EP - 337

JO - Journal of the Taiwan Institute of Chemical Engineers

JF - Journal of the Taiwan Institute of Chemical Engineers

SN - 1876-1070

IS - 4

ER -