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Preparation of Epoxides03:00

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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
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Experimental and Theoretical Studies on Corvol Ether Biosynthesis.

Patrick Rabe1, Aron Janusko1, Bernd Goldfuss2

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Chembiochem : a European Journal of Chemical Biology
|December 5, 2015
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Summary

The biosynthesis of corvol ethers A and B involves hydride shifts. Quantum chemical calculations and labeling experiments confirm that two sequential 1,2-hydride shifts are the preferred pathway for these sesquiterpenes.

Keywords:
NMR spectroscopyisotopic labelingquantum chemical calculationsreaction mechanismsterpene biosynthesis

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Area of Science:

  • Natural Product Biosynthesis
  • Organic Chemistry
  • Biochemistry

Background:

  • Kitasatospora setae produces sesquiterpenes corvol ethers A and B.
  • Understanding the biosynthetic pathways of natural products is crucial for chemical biology.

Purpose of the Study:

  • To elucidate the biosynthetic pathway of corvol ethers A and B.
  • To determine the mechanism of hydride shifts in sesquiterpene biosynthesis.
  • To investigate the stereochemistry of a key reprotonation step.

Main Methods:

  • Quantum chemical calculations to assess energetic favorability of different reaction pathways.
  • Labeling experiments using isotopically labeled farnesyl diphosphate.
  • Incubation of labeled substrates in H2O and D2O to study stereochemical outcomes.

Main Results:

  • The biosynthesis involves either one 1,3- or two sequential 1,2-hydride shifts.
  • Quantum chemical calculations indicated that two sequential 1,2-hydride shifts are energetically favored.
  • Labeling experiments corroborated the computational findings.
  • The stereochemical course of a reprotonation step was analyzed.

Conclusions:

  • The biosynthesis of corvol ethers A and B proceeds via a pathway involving two sequential 1,2-hydride shifts.
  • Computational and experimental data support the proposed biosynthetic mechanism.
  • The study provides insights into the stereoselective nature of sesquiterpene biosynthesis.