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S6879 Sigma

D-Sphingosine

from bovine brain, ~99% (TLC)

Synonym: (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol, 4-Sphingenine, trans-D-erythro-2-Amino-4-octadecene-1,3-diol

  • CAS Number 123-78-4

  • Empirical Formula (Hill Notation) C18H37NO2

  • Molecular Weight 299.49

  •  Beilstein Registry Number 1727294

  •  EC Number 204-651-3

  •  MDL number MFCD00036751

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Properties

Related Categories Cell Biology, Cell Signaling and Neuroscience, Lipid, Lipids in Cell Signaling, Metabolic Pathways,
biological source   from bovine brain
InChI Key   WWUZIQQURGPMPG-KRWOKUGFSA-N
assay   ~99% (TLC)
storage temp.   −20°C
Gene Information   human ... PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584)

Description

Biochem/physiol Actions

A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.

Preparation Note

Prepared from sphingomyelin.

Quality

May contain small amounts of structural analogues.

Application

D-Sphingosine from bovine brain was tested for effects on distribution of clathrin/AP-2 in cultured fibroblasts.8 It was used to prepare vesicles and study the interactions of DNA with bilayers of cationic liposomes.9

Price and Availability


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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles
Peer-Reviewed Papers
15

References

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S7049 D-Sphingosine, synthetic

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