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Conformational Analysis, Thermal Rearrangement, and EI‐MS Fragmentation Mechanism of (1(10) E ,4 E ,6 S ,7 R )‐Germacradien‐6‐ol by 13 C‐Labeling Experiments
Author(s) -
Rabe Patrick,
Barra Lena,
Rinkel Jan,
Riclea Ramona,
Citron Christian A.,
Klapschinski Tim A.,
Janusko Aron,
Dickschat Jeroen S.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507615
Subject(s) - isotopomers , chemistry , conformational isomerism , fragmentation (computing) , stereochemistry , nuclear magnetic resonance spectroscopy , enzyme , organic chemistry , molecule , biology , ecology
An uncharacterized terpene cyclase from Streptomyces pratensis was identified as (+)‐(1(10) E ,4 E ,6 S ,7 R )‐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 ( 13 C 1 )FPP isotopomers (FPP=farnesyl diphosphate) and ( 13 C 15 )FPP were synthesized and enzymatically converted. The products were analyzed using various NMR techniques, including 13 C, 13 C COSY experiments. The ( 13 C)FPP isotopomers were also used to investigate the thermal rearrangement and EI fragmentation of the enzyme product.