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Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases

Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases

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CITRON, Christian A., Patrick RABE, Lena BARRA, Chiaki NAKANO, Tsutomu HOSHINO, Jeroen S. DICKSCHAT, 2014. Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases. In: European Journal of Organic Chemistry. Wiley-Blackwell. 2014(34), pp. 7684-7691. ISSN 1434-243X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201403002

@article{Citron2014Synth-57614, title={Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases}, year={2014}, doi={10.1002/ejoc.201403002}, number={34}, volume={2014}, issn={1434-243X}, journal={European Journal of Organic Chemistry}, pages={7684--7691}, author={Citron, Christian A. and Rabe, Patrick and Barra, Lena and Nakano, Chiaki and Hoshino, Tsutomu and Dickschat, Jeroen S.} }

eng Hoshino, Tsutomu 2022-05-23T08:07:51Z Rabe, Patrick 2022-05-23T08:07:51Z Hoshino, Tsutomu Nakano, Chiaki Dickschat, Jeroen S. Rabe, Patrick Dickschat, Jeroen S. Barra, Lena Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases A flexible, efficient and robust method for the synthesis of isotopically labelled oligoprenyl diphosphates was developed. The method makes use of just a few building blocks (acetone, triethyl phosphonoacetate, and ethyl acetoacetate) from which several isotopomers with deuterium or <sup>13</sup>C-labelling are commercially available or can be easily obtained by synthesis. Besides these building blocks, a few deuterated reagents were used for the introduction of deuterium labelling. Furthermore, the synthesis of [14-<sup>2</sup>H]geranylgeranyl diphosphate is reported. The material was used for a stereochemical analysis of the cyclisation reaction catalysed by tuberculosinyl diphosphate synthase from Mycobacterium tuberculosis. Barra, Lena Nakano, Chiaki Citron, Christian A. terms-of-use Citron, Christian A. 2014

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