D-erythro-C18-Dihydro-D-sphingosine

Description

Dihydrosphingosine (764-22-7) is a biosynthetic precursor of sphingosine. Inhibitor of protein kinase C1?and phospholipases A2 and D2.

Chemical Properties

White Powder

Uses

Sphinganine (d18:0) has been used:

• as a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides
• as a medium supplement to test its effect on growth of yeast cells
• in the preparation of bovine serum albumin lipid complex to investigate its effect on non-lysosomal - glucosylceramidase β2 (GBA2) inhibition

Uses

Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.

Definition

ChEBI: Sphinganine is a 2-aminooctadecane-1,3-diol having (2S,3R)-configuration. It has a role as an EC 2.7.11.13 (protein kinase C) inhibitor, a human metabolite and a mouse metabolite. It is a conjugate base of a sphinganine(1+).

General Description

Sphinganine (d18:0) is a substrate for the enzyme ceramide desaturase. It is synthesized indirectly due to the interconversion of supplemented glycine to serine. Sphinganine (d18:0) is catabolized to ceramide.

Biochem/physiol Actions

Sphinganine (d18:0) levels are not altered in hereditary sensory neuropathy type 1 cells. Accumulation of d18:0 is observed in tumor hypoxia. It is useful as a biomarker for studying microbial diversity.

References

1) Merrill?et al. (1989),?Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for cellular effects of these compounds; Biochemistry,?28?3138 2) Franson?et al. (1992),?Sphingolipid metabolism and signal transduction: inhibition of in vitro phospholipase activity by sphingosine, Biochim. Biophys. Acta?1136?169