Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin

A concise and efficient total synthesis of the lignan natural product larreatricin as well as an unambiguous assignment of configuration of its enantiomers are reported, resolving a long‐held controversy. Enzyme kinetic studies revealed that different polyphenol oxidases show high and remarkably div...

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Autores principales: Martin, Harry J., Kampatsikas, Ioannis, Oost, Rik, Pretzler, Matthias, Al‐Sayed, Emir, Roller, Alexander, Giester, Gerald, Rompel, Annette, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6220842/
https://www.ncbi.nlm.nih.gov/pubmed/30113748
http://dx.doi.org/10.1002/chem.201803785
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author Martin, Harry J.
Kampatsikas, Ioannis
Oost, Rik
Pretzler, Matthias
Al‐Sayed, Emir
Roller, Alexander
Giester, Gerald
Rompel, Annette
Maulide, Nuno
author_facet Martin, Harry J.
Kampatsikas, Ioannis
Oost, Rik
Pretzler, Matthias
Al‐Sayed, Emir
Roller, Alexander
Giester, Gerald
Rompel, Annette
Maulide, Nuno
author_sort Martin, Harry J.
collection PubMed
description A concise and efficient total synthesis of the lignan natural product larreatricin as well as an unambiguous assignment of configuration of its enantiomers are reported, resolving a long‐held controversy. Enzyme kinetic studies revealed that different polyphenol oxidases show high and remarkably divergent enantioselective recognition of this secondary metabolite.
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spelling pubmed-62208422018-11-13 Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin Martin, Harry J. Kampatsikas, Ioannis Oost, Rik Pretzler, Matthias Al‐Sayed, Emir Roller, Alexander Giester, Gerald Rompel, Annette Maulide, Nuno Chemistry Communications A concise and efficient total synthesis of the lignan natural product larreatricin as well as an unambiguous assignment of configuration of its enantiomers are reported, resolving a long‐held controversy. Enzyme kinetic studies revealed that different polyphenol oxidases show high and remarkably divergent enantioselective recognition of this secondary metabolite. John Wiley and Sons Inc. 2018-10-01 2018-10-22 /pmc/articles/PMC6220842/ /pubmed/30113748 http://dx.doi.org/10.1002/chem.201803785 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Martin, Harry J.
Kampatsikas, Ioannis
Oost, Rik
Pretzler, Matthias
Al‐Sayed, Emir
Roller, Alexander
Giester, Gerald
Rompel, Annette
Maulide, Nuno
Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
title Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
title_full Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
title_fullStr Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
title_full_unstemmed Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
title_short Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
title_sort total synthesis, stereochemical assignment, and divergent enantioselective enzymatic recognition of larreatricin
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6220842/
https://www.ncbi.nlm.nih.gov/pubmed/30113748
http://dx.doi.org/10.1002/chem.201803785
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