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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Bibliographic Details
Published in:Chemistry : a European journal 2018-10, Vol.24 (59), p.15756-15760
Main Authors: Martin, Harry J., Kampatsikas, Ioannis, Oost, Rik, Pretzler, Matthias, Al‐Sayed, Emir, Roller, Alexander, Giester, Gerald, Rompel, Annette, Maulide, Nuno
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Catechol Oxidase - chemistry
Chemistry
Communication
Communications
Enantiomers
enantiospecific
Enzyme Activation
Enzyme kinetics
Furans - chemical synthesis
Kinetics
larreatricin
Lignans - chemistry
Molecular Structure
Natural products
polyphenol oxidase
Polyphenols - chemical synthesis
Recognition
Stereoisomerism
Structure-Activity Relationship
Synthesis
total synthesis
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Summary: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. Recognize your mirror image: We report an efficient total synthesis of the lignan natural product larreatricin as well as an unambiguous assignment of configuration of its enantiomers. Enzyme kinetic studies reveal that different families of polyphenol oxidases show high and remarkably divergent enantioselectivity in their recognition of this secondary metabolite.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201803785