Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine
Abstract Enzyme‐catalyzed stereoselective esterification of OH groups in non‐aqueous media has been widely used for kinetic racemate resolution. However, rapid hydrolysis of the ester group was observed as a competing reaction if we attempted to resolve 3‐hydroxy octanoic acid methyl ester with Novo...
Published in: | ChemCatChem |
---|---|
Main Authors: | , , , , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2012
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/cctc.201200355 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcctc.201200355 http://onlinelibrary.wiley.com/wol1/doi/10.1002/cctc.201200355/fullpdf |
id |
crwiley:10.1002/cctc.201200355 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1002/cctc.201200355 2024-06-02T07:57:35+00:00 Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine Braner, Markus Zielonka, Stefan Grzeschik, Julius Krah, Simon Lieb, Sebastian Petras, Daniel Wagner, Xenia Ahmed, Imrana Hüttenhain, Stefan H. 2012 http://dx.doi.org/10.1002/cctc.201200355 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcctc.201200355 http://onlinelibrary.wiley.com/wol1/doi/10.1002/cctc.201200355/fullpdf en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor ChemCatChem volume 4, issue 12, page 2050-2054 ISSN 1867-3880 1867-3899 journal-article 2012 crwiley https://doi.org/10.1002/cctc.201200355 2024-05-03T11:20:09Z Abstract Enzyme‐catalyzed stereoselective esterification of OH groups in non‐aqueous media has been widely used for kinetic racemate resolution. However, rapid hydrolysis of the ester group was observed as a competing reaction if we attempted to resolve 3‐hydroxy octanoic acid methyl ester with Novozym 435 in a non‐aqueous medium with a catalytic amount of the base triethylamine. This hydrolysis away from the stereogenic carbon atom showed stereoselectivity, thus the preparative value of this reaction was inspected closer and it could be extended to higher homologues. 3‐Hydroxy decanoic acid methyl ester, 3‐hydroxy dodecanoic acid methyl ester and 3‐hydroxy tetradecanoic acid methyl ester were also hydrolyzed by Novozym 435 with enhanced reaction rates and moderate selectivities if dissolved in triethylamine. Ethyl mandelate and ethyl lactate were also converted under these conditions. The same phenomenon could also be observed with a 2 % DABCO solution in hexane, whereas secondary amines, for example piperidine, did not influence the reaction. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library ChemCatChem 4 12 2050 2054 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
Abstract Enzyme‐catalyzed stereoselective esterification of OH groups in non‐aqueous media has been widely used for kinetic racemate resolution. However, rapid hydrolysis of the ester group was observed as a competing reaction if we attempted to resolve 3‐hydroxy octanoic acid methyl ester with Novozym 435 in a non‐aqueous medium with a catalytic amount of the base triethylamine. This hydrolysis away from the stereogenic carbon atom showed stereoselectivity, thus the preparative value of this reaction was inspected closer and it could be extended to higher homologues. 3‐Hydroxy decanoic acid methyl ester, 3‐hydroxy dodecanoic acid methyl ester and 3‐hydroxy tetradecanoic acid methyl ester were also hydrolyzed by Novozym 435 with enhanced reaction rates and moderate selectivities if dissolved in triethylamine. Ethyl mandelate and ethyl lactate were also converted under these conditions. The same phenomenon could also be observed with a 2 % DABCO solution in hexane, whereas secondary amines, for example piperidine, did not influence the reaction. |
format |
Article in Journal/Newspaper |
author |
Braner, Markus Zielonka, Stefan Grzeschik, Julius Krah, Simon Lieb, Sebastian Petras, Daniel Wagner, Xenia Ahmed, Imrana Hüttenhain, Stefan H. |
spellingShingle |
Braner, Markus Zielonka, Stefan Grzeschik, Julius Krah, Simon Lieb, Sebastian Petras, Daniel Wagner, Xenia Ahmed, Imrana Hüttenhain, Stefan H. Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine |
author_facet |
Braner, Markus Zielonka, Stefan Grzeschik, Julius Krah, Simon Lieb, Sebastian Petras, Daniel Wagner, Xenia Ahmed, Imrana Hüttenhain, Stefan H. |
author_sort |
Braner, Markus |
title |
Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine |
title_short |
Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine |
title_full |
Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine |
title_fullStr |
Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine |
title_full_unstemmed |
Hydrolysis of Fatty Acid Esters by Candida Antarctica Lipase B (Novozym 435) Dissolved in Anhydrous Triethylamine |
title_sort |
hydrolysis of fatty acid esters by candida antarctica lipase b (novozym 435) dissolved in anhydrous triethylamine |
publisher |
Wiley |
publishDate |
2012 |
url |
http://dx.doi.org/10.1002/cctc.201200355 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcctc.201200355 http://onlinelibrary.wiley.com/wol1/doi/10.1002/cctc.201200355/fullpdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ChemCatChem volume 4, issue 12, page 2050-2054 ISSN 1867-3880 1867-3899 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/cctc.201200355 |
container_title |
ChemCatChem |
container_volume |
4 |
container_issue |
12 |
container_start_page |
2050 |
op_container_end_page |
2054 |
_version_ |
1800740752785932288 |