Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base

[Image: see text] Artemisinin is an important drug to fight malaria. It is produced either by extraction or via a semisynthetic route involving enzyme engineering. A key intermediate to produce artemisinin by the enzymatic route is dihydroartemisinic aldehyde (DHAAl). However, control of the absolut...

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Autores principales: Zanetti, Andrea, Chaumont-Olive, Pauline, Schwertz, Geoffrey, Nascimento de Oliveira, Marllon, Gomez Fernandez, Mario Andrés, Amara, Zacharias, Cossy, Janine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237042/
https://www.ncbi.nlm.nih.gov/pubmed/32454580
http://dx.doi.org/10.1021/acs.oprd.9b00481
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author Zanetti, Andrea
Chaumont-Olive, Pauline
Schwertz, Geoffrey
Nascimento de Oliveira, Marllon
Gomez Fernandez, Mario Andrés
Amara, Zacharias
Cossy, Janine
author_facet Zanetti, Andrea
Chaumont-Olive, Pauline
Schwertz, Geoffrey
Nascimento de Oliveira, Marllon
Gomez Fernandez, Mario Andrés
Amara, Zacharias
Cossy, Janine
author_sort Zanetti, Andrea
collection PubMed
description [Image: see text] Artemisinin is an important drug to fight malaria. It is produced either by extraction or via a semisynthetic route involving enzyme engineering. A key intermediate to produce artemisinin by the enzymatic route is dihydroartemisinic aldehyde (DHAAl). However, control of the absolute configuration of the stereocenter α to the aldehyde is highly challenging. Herein we report a protocol that allows the diastereomeric enrichment of a mixture of (11R)/(11S)-DHAAl to the desired (11R)-DHAAl by utilizing a crystallization-induced diastereomer transformation induced by the Betti base. In addition, the Betti base can be quantitatively recovered and reused after the reaction.
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spelling pubmed-72370422020-05-20 Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base Zanetti, Andrea Chaumont-Olive, Pauline Schwertz, Geoffrey Nascimento de Oliveira, Marllon Gomez Fernandez, Mario Andrés Amara, Zacharias Cossy, Janine Org Process Res Dev [Image: see text] Artemisinin is an important drug to fight malaria. It is produced either by extraction or via a semisynthetic route involving enzyme engineering. A key intermediate to produce artemisinin by the enzymatic route is dihydroartemisinic aldehyde (DHAAl). However, control of the absolute configuration of the stereocenter α to the aldehyde is highly challenging. Herein we report a protocol that allows the diastereomeric enrichment of a mixture of (11R)/(11S)-DHAAl to the desired (11R)-DHAAl by utilizing a crystallization-induced diastereomer transformation induced by the Betti base. In addition, the Betti base can be quantitatively recovered and reused after the reaction. American Chemical Society 2020-01-14 2020-05-15 /pmc/articles/PMC7237042/ /pubmed/32454580 http://dx.doi.org/10.1021/acs.oprd.9b00481 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Zanetti, Andrea
Chaumont-Olive, Pauline
Schwertz, Geoffrey
Nascimento de Oliveira, Marllon
Gomez Fernandez, Mario Andrés
Amara, Zacharias
Cossy, Janine
Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
title Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
title_full Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
title_fullStr Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
title_full_unstemmed Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
title_short Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base
title_sort crystallization-induced diastereoisomer transformation of dihydroartemisinic aldehyde with the betti base
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237042/
https://www.ncbi.nlm.nih.gov/pubmed/32454580
http://dx.doi.org/10.1021/acs.oprd.9b00481
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