Application Notes:
This non-natural L-threo-ceramide contains an acetyl group which allows it to enter easily into cells where it demonstrates
activity different from natural D-erythro-ceramides. N-Acetyl-threo-sphingosine can be converted to the N-acetyl-threosphingosylphosphorylcholine
in the presence of Mn2+ and CDP-choline.1 Glucosyl-N-acetyl-L-threo-sphingosine was found
to be a poorer substrate for beta-glucosidase than the D-erythro isomer but was able to undergo cleavage.2 N-Acetyl-Derythro-
sphingosine demonstrates many of the biological activities associated with ceramides that contain long-chain fatty
acids. However, it has also been found that this N-acetyl-sphingosine may inhibit neutrophil superoxide release,3 stimulation
of DNA synthesis, and phospholipase D activity. N-acetyl-D-erythro-sphingosine is different from sphingosine as seen by its
inability to inhibit protein kinase C or cause calcium release. Ceramide is a fatty acid amide of sphingosine that has many
important biological functions and is the precursor for many complex glycosphingolipids. Ceramide functions as a precursor
in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. Ceramide has been
investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.4
References:
1. M. Ullman and N. Radin “The Enzymatic Formation of Sphingomyelin from Ceramide and Lecithin in Mouse Liver” The Journal of Biological
Chemistry, vol. 249 pp. 1506-1512, 1974
2. K. Sandhoff et al. “Specificity of human glucosylceramide -glucosidase towards synthetic glucosylsphingolipids inserted into liposomes” European
Journal of Biochemistry, vol. 160 pp. 527-535, 1986
3. K. Wong, X. Li, N. Hunchuk “N-Acetylsphingosine (C -ceramide) Inhibited Neutrophil Superoxide Formation and Calcium Influx” Journal of Biological
Chemistry, Vol. 270 pp. 3056-3052, 1995
4. N. S. Radin, “Designing anticancer drugs via the achilles heel: ceramide, allylic ketones, and mitochondria” Bioorganic and Medicinal Chemistry, Vol.
11(10) pp. 2123-2142, 2003