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

ABSTRACT: 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.

SUBMITTER: Martin HJ 

PROVIDER: S-EPMC6220842 | biostudies-other | 2018 Oct

REPOSITORIES: biostudies-other

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

Martin Harry J HJ   Kampatsikas Ioannis I   Oost Rik R   Pretzler Matthias M   Al-Sayed Emir E   Roller Alexander A   Giester Gerald G   Rompel Annette A   Maulide Nuno N  

Chemistry (Weinheim an der Bergstrasse, Germany) 20181001 59

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. ...[more]

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