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Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by <sup>13</sup>C-Labeling Experiments

Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by 13C-Labeling Experiments

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RABE, Patrick, Lena BARRA, Jan RINKEL, Ramona RICLEA, Christian A. CITRON, Tim A. KLAPSCHINSKI, Aron JANUSKO, Jeroen S. DICKSCHAT, 2015. Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by 13C-Labeling Experiments. In: Angewandte Chemie International Edition. Wiley-Blackwell. 54(45), pp. 13448-13451. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201507615

@article{Rabe2015-11-02Confo-57708, title={Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by 13C-Labeling Experiments}, year={2015}, doi={10.1002/anie.201507615}, number={45}, volume={54}, issn={1433-7851}, journal={Angewandte Chemie International Edition}, pages={13448--13451}, author={Rabe, Patrick and Barra, Lena and Rinkel, Jan and Riclea, Ramona and Citron, Christian A. and Klapschinski, Tim A. and Janusko, Aron and Dickschat, Jeroen S.} }

terms-of-use Citron, Christian A. Rabe, Patrick Dickschat, Jeroen S. An uncharacterized terpene cyclase from Streptomyces pratensis was identified as (+)-(1(10)E,4E,6S,7R)-germacradien-6-ol synthase. The enzyme product exists as two interconvertible conformers, resulting in complex NMR spectra. For the complete assignment of NMR data, all fifteen (<sup>13</sup>C<sub>1</sub>)FPP isotopomers (FPP=farnesyl diphosphate) and (<sup>13</sup>C<sub>15</sub>)FPP were synthesized and enzymatically converted. The products were analyzed using various NMR techniques, including <sup>13</sup>C, <sup>13</sup>C COSY experiments. The (<sup>13</sup>C)FPP isotopomers were also used to investigate the thermal rearrangement and EI fragmentation of the enzyme product. eng Klapschinski, Tim A. 2015-11-02 Klapschinski, Tim A. Rabe, Patrick Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by <sup>13</sup>C-Labeling Experiments Janusko, Aron 2022-05-31T12:59:51Z Janusko, Aron Citron, Christian A. Dickschat, Jeroen S. Barra, Lena 2022-05-31T12:59:51Z Barra, Lena Riclea, Ramona Rinkel, Jan Riclea, Ramona Rinkel, Jan

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