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Characterization of a Delta(8)-sphingolipid desaturase from higher plants: A stereochemical and mechanistic study on the origin of E,Z isomers

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Beckmann,  C.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Rattke,  J.
Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society;

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Oldham,  N. J.
Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society;

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Boland,  W.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Citation

Beckmann, C., Rattke, J., Oldham, N. J., Sperling, P., Heinz, E., & Boland, W. (2002). Characterization of a Delta(8)-sphingolipid desaturase from higher plants: A stereochemical and mechanistic study on the origin of E,Z isomers. Angewandte Chemie, International Edition in English, 41(13), 2298-2300. doi:10.1002/1521-3773(20020703)41:13<2298:AID-ANIE2298>3.0.CO;2-G.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0012-9E99-8
Abstract
The simultaneous formation of E and Z double bonds results from the syn elimination of H and/or D atoms from different conformations of 4‐hydroxysphinganine [D4]1. Δ8‐Sphingolipid desaturase from Helianthus annuus is heterologously expressed in yeast and catalyzes the transformation to E olefin 2 (88%) and Z olefin 3 (12%).