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Usage

Uses

Used in Biochemical Research:
N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine is used as a stable isotope-labeled internal standard for the accurate quantification of sphingolipids in biological samples. This application is crucial for ensuring the reliability of mass spectrometry measurements, which are vital in understanding the role of sphingolipids in various cellular processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine serves as a valuable tool for the development of drugs targeting sphingolipid metabolism and signaling pathways. Its use as a standard allows for the precise measurement of drug effects on sphingolipid levels, aiding in the discovery of potential therapeutic agents and their mechanisms of action.
Used in Mass Spectrometry Analysis:
N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine is utilized as a reference compound in mass spectrometry analysis to ensure the accuracy and reproducibility of results. This is particularly important in studies investigating the role of sphingolipids in disease mechanisms and the development of diagnostic markers.
Used in Cell Biology Studies:
In cell biology, N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine is employed to investigate the function and regulation of sphingolipids in cell membranes. Its use as a stable isotope-labeled compound allows researchers to track and quantify changes in sphingolipid levels under various experimental conditions, providing insights into their role in cell signaling and recognition.

Upstream product

• 1670-26-4 sphingosylphosphorylcholine 

Relevant academic research and scientific papers

Raftlike mixtures of sphingomyelin and cholesterol investigated by solid-state 2H NMR spectroscopy

Sphingomyelin is a lipid that is abundant in the nervous systems of mammals, where it is associated with putative microdomains in cellular membranes and undergoes alterations due to aging or neurodegeneration. We investigated the effect of varying the concentration of cholesterol in binary and ternary mixtures with N-palmitoylsphingomyelin (PSM) and 1-palmitoyl-2-oleoyl-sn- glycero-3-phosphocholine (POPC) using deuterium nuclear magnetic resonance (2H NMR) spectroscopy in both macroscopically aligned and unoriented multilamellar dispersions. In our experiments, we used PSM and POPC perdeuterated on the N-acyl and sn-1 acyl chains, respectively. By measuring solid-state 2H NMR spectra of the two lipids separately in mixtures with the same compositions as a function of cholesterol mole fraction and temperature, we obtained clear evidence for the coexistence of two liquid-crystalline domains in distinct regions of the phase diagram. According to our analysis of the first moments M1 and the observed 2H NMR spectra, one of the domains appears to be a liquid-ordered phase. We applied a mean-torque potential model as an additional tool to calculate the average hydrocarbon thickness, the area per lipid, and structural parameters such as chain extension and thermal expansion coefficient in order to further define the two coexisting phases. Our data imply that phase separation takes place in raftlike ternary PSM/POPC/cholesterol mixtures over a broad temperature range but vanishes at cholesterol concentrations equal to or greater than a mole fraction of 0.33. Cholesterol interacts preferentially with sphingomyelin only at smaller mole fractions, above which a homogeneous liquid-ordered phase is present. The reasons for these phase separation phenomena seem to be differences in the effects of cholesterol on the configurational order of the palmitoyl chains in PSM-d31 and POPC-d31 and a difference in the affinity of cholesterol for sphingomyelin observed at low temperatures. Hydrophobic matching explains the occurrence of raftlike domains in cellular membranes at intermediate cholesterol concentrations but not saturating amounts of cholesterol.