Sphingosine degradation

The results of these experiments have been recalculated from the data of Zabin and Mead (1953, 1954) and Sprinson and Coulon (1954) and are presented in Table 1. It is immediately apparent from this data that acetate labelled in either the one or two positions gives rise exclusively to the hydrocarbon portion of the sphingosine. Degradation of the palmitic acid derived from the sphingosine labelled with acetate-2-shows that carbon 4 is 3 to 5 times richer in than carbons 3 or 5. This is consistent with the pattern observed during fatty acid synthesis... 

SIP is formed from sphingosine by sphingosine kinases (SphKs). Degradation of SIP occurs either reversibly by lipid phosphate phosphohydrolases (LPPs) and SIP phosphatases (SPPs), or irreversibly by SIP lyase (SPL) (Fig. 1). The localization of SIP production is highly important since SIP plays a role both as extracellular mediator and as intracellular... 

Bergstrom, J., Kurtz, M.B. and Spiegel, S., 2000, Molecular cloning and characterization of a novel lipid phosphohydrolase that degrades sphingosine 1-phosphate and induces cell death, Proc. Nat. Acad. Sci U.S.A. 97 7859-7864. 

Structural studies of glycosphingolipids involves determination of the structure of the oligosaccharide chain and of the lipid moiety. For the oligosaccharide chain, it is necessary to determine the composition, molar ratio, and sequence of the monosaccharides, their pyranose or furanose nature, and the position of glycosidic bonds and their configuration for the lipid moiety, the composition of the fatty acids and sphingosine bases must be determined. Used for these purposes are the classical, chemical methods, conventionally accepted in the chemistry of carbohydrates and lipids and based on the degradation of compounds, enzymic, and physicochemical methods, primarily mass spectrometry and n.m.r. spectroscopy. 

California Institute of Technology, 1940-1942. Ph.D., May 1942. Thesis I. Synthesis of Fluorinated Analogs of Thyroxine. II. Oxidative Degradation of Sphingosine Analogs. III. Inhibition in the Slow Muscle of Pecten. Professional Experience... 

Oleamide, a lipid originally named cerebrodiene, was first iso lated from partially sleep-deprived cats (Lerner et al 1994). The molecule, with the chemical formula C18H35NO, is a long-chain base structurally related to sphingosine and sphinganine (Lerner et al 1994). Oleamide, or cerebrodiene, is chemically characterized as cis-9,10-octadecenoamide (Cravatt et al 1995). Oleamide is degraded by the brain enzyme fatty acid amide hydrolase (FAAH), which also degrades anandamide (Cravatt et al. Nature 1996). 

Ceramide can be generated through several different pathways, such as synthesis within the cell, hydrolysis of SHM by SHM-ase, and breakdown of glycosphingolipids. The degradation of ceramide by acid ceramidase hberates sphingosine, a free fatty acid in the lysosomal compartment... 

The geometry of the double bond of sphingosine and of some natural sphingosine derivatives has been elucidated.9-11 The dia-stereoisomeric relationship of the amino and 3-hydroxyl groups is erythro this was proved by degradation and synthesis.12... 

The degradation of N-acetyl-di-0-acetyl-CI8-sphingosine (4) with ozone gives13,14 3-amino-2-hydroxybutyrolactone (5) and tetra-decanal (6). 

The absolute configuration of C-2 in the sphingosine molecule was also proved, because oxidation with hydrogen perioxide (following the degradation with ozone) led to L-serine. 

The mono-unsaturated aminotriol, namely, the dehydrophyto-sphingosine (11), was similarly obtained from soya-bean and flax phosphatides. On catalytic hydrogenation, compound 11 gives phytosphingosine, and, by degradation with ozone, 7-amino-5,6,8-tri-hydroxyoctanal (12) and decanal (13). 

The anomeric configuration of the D-galactopyranosyl group on the sphingosine moiety was determined by the degradation method of... 

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