Publikation: 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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2015
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Rabe, Patrick
Rinkel, Jan
Riclea, Ramona
Citron, Christian A.
Klapschinski, Tim A.
Janusko, Aron
Dickschat, Jeroen S.
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Angewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(45), pp. 13448-13451. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201507615
Zusammenfassung
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 (13C1)FPP isotopomers (FPP=farnesyl diphosphate) and (13C15)FPP were synthesized and enzymatically converted. The products were analyzed using various NMR techniques, including 13C, 13C COSY experiments. The (13C)FPP isotopomers were also used to investigate the thermal rearrangement and EI fragmentation of the enzyme product.
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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. 2015, 54(45), pp. 13448-13451. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201507615BibTex
@article{Rabe2015-11-02Confo-57708,
year={2015},
doi={10.1002/anie.201507615},
title={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},
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.}
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