Chapter 17 Lipids 17 6 Sphingolipids General Organic

Sphingosine is an 18 -carbon unsaturated amino alcohol. Sphingosine General, Organic, and Biological Chemistry

Ceramides In a ceramide, § the NH 2 group in sphingosine is attached by

Sphingolipids § are similar to glycerophospholipids § contain sphingosine, a fatty acid, phosphate, and

Sphingomyelin § is a sphingolipid found in nerve cells § bonds the —OH of

Glycosphingolipids are § sphingolipids that contain monosaccharides attached by a -glycosidic bond to the

Cerebrosides § contain galactose or glucose attached by a -glycosidic bond to the —OH

Gangliosides Ganglia: Nerve tussues at CNS/PNS Gangliosides § are sphingolipids that contain chains of

Gangliosides (continued) GM 2 is a ganglioside § that accumulates in Tay-Sachs disease when

Lipid Diseases (Lipidoses) In many lipid diseases, § the deficiency of an enzyme causes

Learning Check Identify each as a 1) fatty acid 3) amino alcohol 5) glycosphingolipid

Solution Identify each as a 1) fatty acid 3) amino alcohol 5) glycosphingolipid 2)

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Sphingolipids § are similar to glycerophospholipids § contain sphingosine, a fatty acid, phosphate, and an amino alcohol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 4

Sphingomyelin § is a sphingolipid found in nerve cells § bonds the —OH of a ceramide to a phosphate ester of choline General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 5

Glycosphingolipids are § sphingolipids that contain monosaccharides attached by a -glycosidic bond to the —OH group of ceramide General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 6

Cerebrosides § contain galactose or glucose attached by a -glycosidic bond to the —OH group of ceramide § are found in the brain and the myelin sheath § are important in cellular recognition and tissue immunity General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 7

Gangliosides Ganglia: Nerve tussues at CNS/PNS Gangliosides § are sphingolipids that contain chains of two to seven monosaccharides § are important in neurons § are found on cell membrane surfaces § act as receptors for hormones, viruses, and drugs § can cause genetic diseases if they accumulate General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 8

Gangliosides (continued) GM 2 is a ganglioside § that accumulates in Tay-Sachs disease when hexoamidase A is defective General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 9

Lipid Diseases (Lipidoses) In many lipid diseases, § the deficiency of an enzyme causes the accumulation of glycolipids General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 10

Learning Check Identify each as a 1) fatty acid 3) amino alcohol 5) glycosphingolipid A. Glyceryl trioleate B. Cephalin C. Choline D. Galactocerebroside E. Palmitic acid 2) triacylglycerol 4) glycerophospholipid General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 11

Solution Identify each as a 1) fatty acid 3) amino alcohol 5) glycosphingolipid 2) triacylglycerol 4) glycerophospholipid A. Glyceryl trioleate B. Cephalin C. Choline D. Galactocerebroside E. Palmitic acid 2) triacylglycerol 4) glycerophospholipid 3) amino alcohol 5) glycosphingolipid 1) fatty acid General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 12