Stereoselective synthesis of unnatural (2S,3S)-6-hydroxy-4-sphingenine-containing sphingolipids.

Leichnitz D, Pflanze S, Beemelmanns C (2019) Stereoselective synthesis of unnatural (2S,3S)-6-hydroxy-4-sphingenine-containing sphingolipids. Org Biomol Chem 17(29), 6964-6969. PubMed

ILRS Authors

Daniel Leichnitz Sebastian Pflanze


Exploitation and total synthesis of new microbial sphingolipid-type signaling molecules

The Effect of Bacterial Natural Products on Multicellular Development


6-Hydroxy-(4E)-sphingenine-containing sphingolipids are found in mammalian and bacterial membranes and have multiple intra- and intercellular functions. Most sphingolipids contain a (2S,3R)-2-amino-1,3-diol core structure, but only limited examples of unnatural (2S,3S)-2-amino-1,3-diol derivates have so far been reported. Using an underexplored hydrozirconation-transmetalation reaction and an unusual three-step-one-pot deprotection sequence, we were able to synthesize several unnatural (2S,3S)-6-hydroxy-(4E)-sphingenine-containing sphingolipids in only three (protected) or four (deprotected) consecutive steps, respectively, including a fluoresence-labeled derivative suitable for future biological studies.


doi: 10.1039/c9ob00990f PMID: 31134244

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