Syntheses of 3‐C‐Methylceramides

Abstract

We report on the synthesis of a series of 3-C- methylceramide derivatives 2a,b, 12a,b, 13a,b, and 14a,b.

Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts)

“…Figure 1 shows the structures of the ceramide analogues studied. Compounds 1 and 4 and compounds 7-11 were synthesized as described in references [24][25][26][27]. The 3-C-methylceramides 2 and 3 were prepared as described previously [27].…”

“…Compounds 1 and 4 and compounds 7-11 were synthesized as described in references [24][25][26][27]. The 3-C-methylceramides 2 and 3 were prepared as described previously [27]. Compound 5 (rac-(2'-tridecylcyclopropyl)-(3R)-3-hydroxy-(2S)-2-(dodecanamido)propanol) was prepared by cyclopropanation of N-lauroyl-sphingosine according to a modification of the Simmons-Smith reaction [28,29]; compound 6 (rac-1-(5', 5'-dimethyl1',3'-dioxaN-2'-yl)-1-(dodecanoylamino)-(E)-pentadec-3-en-2-ol; was prepared by nitro aldol addition [30] of 2,2-dimethyl-5-(nitromethyl)-1,3-dioxane to tetradecanal, followed by catalytic hydrogenation and N-acylation (P. Sawatzki, Ph.D. Thesis, University of Bonn, 2003).…”

Synthetic α-Mannosyl Ceramide as a Potent Stimulant for an NKT Cell Repertoire Bearing the Invariant Vα19-Jα26 TCR α Chain

“…Several approaches have been reported for the synthebe reactive to certain glycosphingolipids (GSLs) such sis of azidosphingosine, which is particularly useful as as α-galactosyl ceramide (α-GalCer) in the context of a glycosylation acceptor [23][24][25][26][27][28]. However, these meth-CD1d [10].…”

An Efficient and General Enantioselective Synthesis of Sphingosine, Phythosphingosine, and 4-Substituted Derivatives

“…The most important sphingolipids are sphingosine and phytosphingosine, which when acylated with a fatty acid and glycosylated with galactose produce galactosylceramide (GalCer) and α-GalCer (KRN7000), respectively (Figure ). Recently, structurally modified sphingosines and phytosphingosines , have attracted more attention because some of their analogues have been observed to introduce morphological changes in neuronal cells and behave as enzyme inhibitors …”