Sphingosine
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | Sphingosine | ||||||||||||||||||
other names |
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Molecular formula | C 18 H 37 NO 2 | ||||||||||||||||||
Brief description |
white solid |
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properties | |||||||||||||||||||
Molar mass | 299.49 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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solubility |
poor in chloroform (20 g l −1 at 20 ° C) |
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safety instructions | |||||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Sphingosine is a monounsaturated amino alcohol whose molecules consist of 18 carbon atoms , one amino group and two hydroxyl groups . Sphingosine forms the backbone of sphingolipids , a class of membrane lipids in which the amino group of sphingosine is bound to a fatty acid with an amide bond .
Sphingolipids are divided into ceramides , sphingomyelins , cerebrosides , gangliosides and sulfatides . They are found in nerve tissue , they play an important role in signal transmission and the interaction of individual cells .
synthesis
Sphingosine is synthesized in the body from palmitoyl-CoA and serine .
First, palmitoyl-CoA and serine are condensed to 3-dehydrosphinganine . This is then reduced to dihydrosphingosine (sphinganine) with the help of NADPH , and then further oxidized to sphingosine with the help of FAD .
Web links
Individual evidence
- ↑ a b c data sheet D-Sphingosine from bovine brain from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).