193222-34-3

Usage

Chemical class

sphingoid bases

Structural similarity

similar to sphingosine, but lacks a hydroxyl group on the C1 position of the sphingoid base

Role

key intermediate in the sphingolipid biosynthesis pathway, involved in the formation of complex sphingolipids

Importance

plays important roles in cell membrane structure and cellular signaling

Potential involvement

in various physiological and pathological processes, including cellular apoptosis, inflammation, and cancer

Therapeutic target

considered a potential target for therapeutic interventions in diseases related to sphingolipid metabolism.

Upstream product

• 1284251-22-4 (4S,5R)-4-methyl-5-[(E)-pentadec-1-en-1-yl]oxazolidin-2-one 
• 1284251-20-2 (E,2S,3R)-2-tert-butyloxycarbonylamino-3-hydroxy-octadec-4-ene 
• 1186628-26-1 (-)-(Rs)-N-[(1S,2R,E)-2-(methoxymethoxy)-1-(methylheptadec-3-enyl)]-2-methylpropane-2-sulfinamide 

Downstream Products

• 97014-46-5 spisulosine 
• 1294447-15-6 N-((2S,3R,E)-3-hydroxyoctadec-4-en-2-yl)-2-phenylacetamide 

Relevant academic research and scientific papers

Straightforward access to spisulosine and 4,5-dehydrospisulosine stereoisomers: Probes for profiling ceramide synthase activities in intact cells

A stereoselective synthesis of spisulosine (ES285) and 4,5- dehydrospisulosine stereoisomers is described. Hydrozirconation of 1-pentadecyne with Schwartz reagent, followed by diastereocontrolled addition to l- or d-alaninal afforded the required 2-amino-1,3-diol framework. The resulting sphingoid bases revealed as excellent probes for the profiling of ceramide synthase activity in intact cells. Among the sphingoid bases described in this work, spisulosine (ES285), RBM1-77, and RBM1-73 were the most suitable ones because of their highest acylation rates. These molecules should prove useful to study the role of the different ceramide synthases and the resulting N-acyl (dihydro)ceramides in cell fate.

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

High-yielding synthesis of sphingoid-type bases

(Chemical Equation Presented) An efficient methodology for the synthesis of sphingoid-type bases is reported. It involves the stereoselective addition of a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl imines and a cross-metathesis reac