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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Authors: | Patrick Rabe Lena Barra Jan Rinkel Dr Ramona Riclea Dr Christian A Citron Tim A Klapschinski Aron Janusko Prof?Dr Jeroen S Dickschat |
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Institution: | Kekulé‐Institut für Organische Chemie und Biochemie, Rheinische Friedrich‐Wilhelms‐Universit?t Bonn, Gerhard‐Domagk‐Strasse 1, 53121 Bonn (Germany) |
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Abstract: | 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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Keywords: | conformation analysis isotopic labeling mass spectrometry NMR spectroscopy terpenoids |
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