Characterization of a Δ8-Sphingolipid Desaturase from Higher Plants: A Stereochemical and Mechanistic Study on the Origin of E,Z Isomers†
Christoph Beckmann Dipl.-Chem.
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorJanine Rattke
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorNeil J. Oldham Dr.
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorPetra Sperling Dr.
Institut für Allgemeine Botanik, Universität Hamburg Ohnhorststr. 18, 22609 Hamburg (Germany)
Search for more papers by this authorErnst Heinz Prof. Dr.
Institut für Allgemeine Botanik, Universität Hamburg Ohnhorststr. 18, 22609 Hamburg (Germany)
Search for more papers by this authorWilhelm Boland Prof. Dr.
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorChristoph Beckmann Dipl.-Chem.
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorJanine Rattke
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorNeil J. Oldham Dr.
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorPetra Sperling Dr.
Institut für Allgemeine Botanik, Universität Hamburg Ohnhorststr. 18, 22609 Hamburg (Germany)
Search for more papers by this authorErnst Heinz Prof. Dr.
Institut für Allgemeine Botanik, Universität Hamburg Ohnhorststr. 18, 22609 Hamburg (Germany)
Search for more papers by this authorWilhelm Boland Prof. Dr.
Max-Planck-Institut für Chemische Ökologie Winzerlaer Str. 10, 07745 Jena (Germany) Fax: (+49) 3641-571-202
Search for more papers by this authorWe thank the Deutsche Forschungsgemeinschaft (SFB 436) and the Fonds der Chemischen Industrie for financial support.
Graphical 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%).
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