Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media
ABSTRACT S‐1‐(2‐Furyl) ethanol serves as an important chiral building block for the preparation of various natural products, fine chemicals, and is widely used in the chemical and pharmaceutical industries. In this work, lipase‐catalyzed kinetic resolution of (R/S)‐1‐(2‐furyl) ethanol using differen...
Published in: | Chirality |
---|---|
Main Authors: | , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2014
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/chir.22317 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.22317 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.22317 |
id |
crwiley:10.1002/chir.22317 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1002/chir.22317 2024-09-09T19:08:54+00:00 Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media Devendran, Saravanan Yadav, Ganapati D. 2014 http://dx.doi.org/10.1002/chir.22317 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.22317 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.22317 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chirality volume 26, issue 6, page 286-292 ISSN 0899-0042 1520-636X journal-article 2014 crwiley https://doi.org/10.1002/chir.22317 2024-06-25T04:12:53Z ABSTRACT S‐1‐(2‐Furyl) ethanol serves as an important chiral building block for the preparation of various natural products, fine chemicals, and is widely used in the chemical and pharmaceutical industries. In this work, lipase‐catalyzed kinetic resolution of (R/S)‐1‐(2‐furyl) ethanol using different acyl donors was investigated. Vinyl esters are good acyl donors vis‐à‐vis alkyl esters for kinetic resolution. Among them, vinyl acetate was found to be the best acyl donor. Different immobilized lipases such as Rhizomucor miehei lipase, Thermomyces lanuginosus lipase, and Candida antarctica lipase B were evaluated for this reaction, among which C . antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n‐heptane as solvent. The effect of various parameters was studied in a systematic manner. Maximum conversion of 47% and enantiomeric excess of the substrate (ee s ) of 89% were obtained in 2 h using 5 mg of enzyme loading with an equimolar ratio of alcohol to vinyl acetate at 60°C at a speed of 300 rpm in a batch reactor. From the analysis of progress curve and initial rate data, it was concluded that the reaction followed the ordered bi–bi mechanism with dead‐end ester inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is more economical, green, and easily scalable than the chemical processes. Chirality 26:286–292, 2014 . © 2014 Wiley Periodicals, Inc. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Chirality 26 6 286 292 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
ABSTRACT S‐1‐(2‐Furyl) ethanol serves as an important chiral building block for the preparation of various natural products, fine chemicals, and is widely used in the chemical and pharmaceutical industries. In this work, lipase‐catalyzed kinetic resolution of (R/S)‐1‐(2‐furyl) ethanol using different acyl donors was investigated. Vinyl esters are good acyl donors vis‐à‐vis alkyl esters for kinetic resolution. Among them, vinyl acetate was found to be the best acyl donor. Different immobilized lipases such as Rhizomucor miehei lipase, Thermomyces lanuginosus lipase, and Candida antarctica lipase B were evaluated for this reaction, among which C . antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n‐heptane as solvent. The effect of various parameters was studied in a systematic manner. Maximum conversion of 47% and enantiomeric excess of the substrate (ee s ) of 89% were obtained in 2 h using 5 mg of enzyme loading with an equimolar ratio of alcohol to vinyl acetate at 60°C at a speed of 300 rpm in a batch reactor. From the analysis of progress curve and initial rate data, it was concluded that the reaction followed the ordered bi–bi mechanism with dead‐end ester inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is more economical, green, and easily scalable than the chemical processes. Chirality 26:286–292, 2014 . © 2014 Wiley Periodicals, Inc. |
format |
Article in Journal/Newspaper |
author |
Devendran, Saravanan Yadav, Ganapati D. |
spellingShingle |
Devendran, Saravanan Yadav, Ganapati D. Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media |
author_facet |
Devendran, Saravanan Yadav, Ganapati D. |
author_sort |
Devendran, Saravanan |
title |
Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media |
title_short |
Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media |
title_full |
Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media |
title_fullStr |
Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media |
title_full_unstemmed |
Lipase‐Catalyzed Kinetic Resolution of (±)‐1‐(2‐Furyl) Ethanol in Nonaqueous Media |
title_sort |
lipase‐catalyzed kinetic resolution of (±)‐1‐(2‐furyl) ethanol in nonaqueous media |
publisher |
Wiley |
publishDate |
2014 |
url |
http://dx.doi.org/10.1002/chir.22317 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.22317 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.22317 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Chirality volume 26, issue 6, page 286-292 ISSN 0899-0042 1520-636X |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chir.22317 |
container_title |
Chirality |
container_volume |
26 |
container_issue |
6 |
container_start_page |
286 |
op_container_end_page |
292 |
_version_ |
1809823169481015296 |