Publikation: Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases
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2014
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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
Zusammenfassung
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 13C-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 [14-2H]geranylgeranyl diphosphate is reported. The material was used for a stereochemical analysis of the cyclisation reaction catalysed by tuberculosinyl diphosphate synthase from Mycobacterium tuberculosis.
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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.201403002BibTex
@article{Citron2014Synth-57614,
year={2014},
doi={10.1002/ejoc.201403002},
title={Synthesis of Isotopically Labelled Oligoprenyl Diphosphates and Their Application in Mechanistic Investigations of Terpene Cyclases},
number={34},
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.}
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<dcterms:abstract xml:lang="eng">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.</dcterms:abstract>
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