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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-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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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]

PMID: 30113748

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