KOPS - The Institutional Repository of the University of Konstanz

Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by <sup>13</sup>C,<sup>13</sup>C COSY NMR Spectroscopy

Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy

Cite This

Files in this item

Files Size Format View

There are no files associated with this item.

BARRA, Lena, Kerstin IBROM, Jeroen S. DICKSCHAT, 2015. Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy. In: Angewandte Chemie International Edition. Wiley-Blackwell. 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765

@article{Barra2015-05-26Struc-57617, title={Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy}, year={2015}, doi={10.1002/anie.201501765}, number={22}, volume={54}, issn={1433-7851}, journal={Angewandte Chemie International Edition}, pages={6637--6640}, author={Barra, Lena and Ibrom, Kerstin and Dickschat, Jeroen S.} }

Barra, Lena Ibrom, Kerstin eng Ibrom, Kerstin 2022-05-23T08:12:43Z Barra, Lena 2022-05-23T08:12:43Z Dickschat, Jeroen S. Dickschat, Jeroen S. terms-of-use Feeding of (2,3,4,5,6-<sup>13</sup>C<sub>5</sub>)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a <sup>13</sup>C,<sup>13</sup>C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-<sup>13</sup>C)- and (4,6-<sup>13</sup>C<sub>2</sub>)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the <sup>13</sup>C,<sup>13</sup>C couplings. Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by <sup>13</sup>C,<sup>13</sup>C COSY NMR Spectroscopy 2015-05-26

This item appears in the following Collection(s)

Search KOPS


Browse

My Account