Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre
Abstract The Biginelli synthesis is a classic tricomponent reaction known to result in polyfunctionalized dihydropyrimidinone (DHPM) derivatives. Herein, we described a chemo‐enzymatic strategy for obtaining enantiomerically enriched hydroxy‐DHPMs. These compounds were previously esterified with but...
Published in: | European Journal of Organic Chemistry |
---|---|
Main Authors: | , , , , |
Other Authors: | |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2022
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/ejoc.202200331 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.202200331 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejoc.202200331 |
id |
crwiley:10.1002/ejoc.202200331 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1002/ejoc.202200331 2024-03-17T08:54:01+00:00 Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre Zanin, Lucas Lima Brito Matos, Thiago Kelvin Leitão, Andrei Ellena, Javier Porto, André Luiz Meleiro Fundação de Amparo à Pesquisa do Estado de São Paulo 2022 http://dx.doi.org/10.1002/ejoc.202200331 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.202200331 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejoc.202200331 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Organic Chemistry volume 2022, issue 38 ISSN 1434-193X 1099-0690 Organic Chemistry Physical and Theoretical Chemistry journal-article 2022 crwiley https://doi.org/10.1002/ejoc.202200331 2024-02-22T01:52:10Z Abstract The Biginelli synthesis is a classic tricomponent reaction known to result in polyfunctionalized dihydropyrimidinone (DHPM) derivatives. Herein, we described a chemo‐enzymatic strategy for obtaining enantiomerically enriched hydroxy‐DHPMs. These compounds were previously esterified with butyric or acetic anhydride and were later submitted to hydrolysis reactions catalysed by lipase B from Candida antarctica . Although the stereogenic centre is far from the reaction site (4–5 bonds), moderate to excellent enantiomeric excess values were obtained (up to 99 %). Docking studies were performed in parallel to elucidate the binding modes of some molecules with the CALB active site, and were able to provide information on the enantiospecificity of these compounds in the hydrolysis reaction. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Organic Chemistry 2022 38 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
topic |
Organic Chemistry Physical and Theoretical Chemistry |
spellingShingle |
Organic Chemistry Physical and Theoretical Chemistry Zanin, Lucas Lima Brito Matos, Thiago Kelvin Leitão, Andrei Ellena, Javier Porto, André Luiz Meleiro Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre |
topic_facet |
Organic Chemistry Physical and Theoretical Chemistry |
description |
Abstract The Biginelli synthesis is a classic tricomponent reaction known to result in polyfunctionalized dihydropyrimidinone (DHPM) derivatives. Herein, we described a chemo‐enzymatic strategy for obtaining enantiomerically enriched hydroxy‐DHPMs. These compounds were previously esterified with butyric or acetic anhydride and were later submitted to hydrolysis reactions catalysed by lipase B from Candida antarctica . Although the stereogenic centre is far from the reaction site (4–5 bonds), moderate to excellent enantiomeric excess values were obtained (up to 99 %). Docking studies were performed in parallel to elucidate the binding modes of some molecules with the CALB active site, and were able to provide information on the enantiospecificity of these compounds in the hydrolysis reaction. |
author2 |
Fundação de Amparo à Pesquisa do Estado de São Paulo |
format |
Article in Journal/Newspaper |
author |
Zanin, Lucas Lima Brito Matos, Thiago Kelvin Leitão, Andrei Ellena, Javier Porto, André Luiz Meleiro |
author_facet |
Zanin, Lucas Lima Brito Matos, Thiago Kelvin Leitão, Andrei Ellena, Javier Porto, André Luiz Meleiro |
author_sort |
Zanin, Lucas Lima |
title |
Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre |
title_short |
Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre |
title_full |
Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre |
title_fullStr |
Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre |
title_full_unstemmed |
Biocatalytic Kinetic Resolution to Access Enantiomerically Enriched Dihydropyrimidinone/Thiones through Recognition of a Remote Stereocentre |
title_sort |
biocatalytic kinetic resolution to access enantiomerically enriched dihydropyrimidinone/thiones through recognition of a remote stereocentre |
publisher |
Wiley |
publishDate |
2022 |
url |
http://dx.doi.org/10.1002/ejoc.202200331 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.202200331 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejoc.202200331 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Organic Chemistry volume 2022, issue 38 ISSN 1434-193X 1099-0690 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejoc.202200331 |
container_title |
European Journal of Organic Chemistry |
container_volume |
2022 |
container_issue |
38 |
_version_ |
1793770176753172480 |