Lessons from 1,3-Hydride Shifts in Sesquiterpene Cyclizations

J. Rinkel, P. Rabe, P.V. Garbeva, Jeroen Dickschat

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Abstract

Stereospecifically labelled precursors were subjected to conversion by seven bacterial sesquiterpene cyclases to investigate the stereochemistry of their initial 1,10-cyclisation-1,3-hydride shift cascades. Enzymes with products of known absolute configuration showed a coherent stereochemical course, except for (−)-α-amorphene synthase, for which the obtained results are better explained by an initial 1,6-cyclisation. The link between the absolute configuration of the product and the stereochemical course of the 1,3-hydride shifts enabled assignment of the absolute configurations of three enzyme products, which were confirmed independently through the absolute configuration of the common byproduct germacrene D-4-ol.
Original languageEnglish
Pages (from-to)13593-13596
JournalAngewandte Chemie
Volume55
Issue number43
Early online date26 Sep 2016
DOIs
Publication statusPublished - 2016

Keywords

  • international

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