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

Beckmann, C.; Rattke, J.; Oldham, N. J.; Sperling, P.; Heinz, E.; Boland, W.

doi:10.1002/1521-3773(20020703)41:13<2298::AID-ANIE2298>3.0.CO;2-G

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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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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: https://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%).