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Chapter 9: Problem 7

Draw the structures of the following membrane lipids: (a) 1-stearoyl-2-oleoyl-3-phosphatidylethanolamine (b) palmitoylsphingomyelin (c) myristoyl- \(\beta\)-D-glucocerebroside.

Short Answer

Expert verified
The drawn structures of the three lipids, namely 1-stearoyl-2-oleoyl-3-phosphatidylethanolamine, palmitoylsphingomyelin, and myristoyl-\(\beta\)-D-glucocerebroside, involve various complexities due to the presence of different functional groups attached to different base structures.

Step by step solution

01

Draw 1-stearoyl-2-oleoyl-3-phosphatidylethanolamine

1. Begin with the glycerol backbone, which consists of three carbon atoms. 2. At the first carbon, attach the stearoyl group. This is a long chain fatty acid with 18 carbon atoms.3. At the second carbon, attach the oleoyl group, another fatty acid with 18 carbon atoms and one cis double bond.4. At the third carbon, attach the phosphate group (\(PO_4\)) linked to an ethanolamine group.
02

Draw palmitoylsphingomyelin

1. Start with a sphingosine backbone, which includes a long chain base with two hydroxyl (\(OH\)) groups, an amino (\(NH_2\)) group, and a double bond. 2. Join a palmitoyl group (a 16-carbon fatty acid) to the amino group. 3. Connect a phosphorylcholine group to the first \(OH\) group of the sphingosine.
03

Draw myristoyl-\(\beta\)-D-glucocerebroside

1. Start with a ceramide base (a sphingosine backbone with a fatty acid attached to the amino group). In this case, attach a myristoyl group, a 14-carbon fatty acid.2. Attach a glucose molecule (in \(\beta\) configuration) to the first \(OH\) group of the sphingosine. This glucose is attached through an oxygen bridge, forming a glycosidic bond.

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Most popular questions from this chapter

In the inositol signaling pathway, both \(\mathrm{IP}_{3}\) and diacylglycerol (DAG) are hormonal second messengers. If certain protein kinases in cells are activated by binding \(\mathrm{Ca}\), how do \(\mathrm{IP}_{3}\) and \(\mathrm{DAG}\) act in a complementary fashion to elicit cellular responses inside cells?

Write the molecular formulas for the following fatty acids: (a) nervonic acid (cis- \(\Delta^{15}\)-tetracosenoate; 24 carbons); (b) vaccenic acid (cis- \(\Delta^{11}\)-octadecenoate); and (c) EPA (all cis- \(\Delta^{5,8,11,14,17}\)-eicosapentaenoate).

Many snake venoms contain phospholipase \(\mathrm{A}_{2}\) that catalyzes the degradation of glycerophospholipids into a fatty acid and a "lysolecithin." The amphipathic nature of lysolecithins allows them to act as detergents in disrupting the membrane structure of red blood cells, causing them to rupture. Draw the structures of phosphatidyl serine (PS) and the products (including a lysolecithin) that result from the reaction of PS with phospholipase \(A_{2}\).

Mammalian platelet activating factor (PAF), a messenger in signal transduction, is a glycerophospholipid with an ether linkage at \(C-1\). PAF is a potent mediator of allergic responses, inflammation, and the toxic-shock syndrome. Draw the structure of PAF (1-alkyl-2-acetylphosphatidyl-choline), where the 1 -alkyl group is a \(\mathrm{C}_{16}\) chain.

Docosahexaenoic acid, \(22: 6 \Delta^{4,7,10,13,16,19}\), is the predominate fatty acyl group in the C-2 position of glycerol-3-phosphate in phosphatidylethanolamine and phosphatidylcholine in many types of fish. (a) Draw the structure of docosahexaenoic acid (all double bonds are cis). (b) Classify docosahexaenoic acid as an omega-3, omega-6, or omega-9 fatty acid.
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