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#phosphoglycerides

2 public questions tagged with this topic.

Which of the following forms mixed bilayers with phosphoglycerides?

Phosphoglycerides and sphingomyelin can co-assemble into stable mixed bilayers because both possess two hydrophobic tails and cylindrical geometry compatible with lamellar phase, unlike lysophospholipids that form micelles or cardiolipin that favors hexagonal inverted phases due to small headgroup. Sphingomyelin's fatty acid amidated to sphingosine resembles phosphatidylcholine's diacylglycerol moiety in hydrophobic thickness, allowing van der Waals matching and hydrophobic mismatch avoidance, enabling fluid mosaic continuity. Moreover sphingomyelin synthesis itself links the two classes: sphingomyelin synthase SMS1 and SMS2 in Golgi and plasma membrane transfer phosphocholine from phosphatidylcholine onto ceramide producing diacylglycerol signaling lipid activating protein kinase D. In model membranes, sphingomyelin-phosphatidylcholine mixtures exhibit miscibility with cholesterol-induced phase separation into liquid-ordered rafts, explaining outer leaflet enrichment and organization of GPI-anchored proteins. Cholesterol alone is too small with single hydroxyl to form bilayer alone, requiring phospholipid matrix, while phosphatidylinositol prefers inner leaflet due to polyphosphate negative charge. Thus sphingomyelin uniquely partners with phosphoglycerides to build heterogeneous mosaic bilayer with domains.

Ref: Alberts et al., Molecular Biology of the Cell, 7th ed., Chapter 10: Mixed Bilayers of Sphingomyelin.

Which of the following linkages is found in sphingomyelin but not in phosphoglycerides?

Phosphoglycerides use glycerol backbone where fatty acids are linked to sn-1 and sn-2 hydroxyls via O-ester bonds, susceptible to phospholipase A1 and A2 hydrolysis generating lysophospholipids and free fatty acids like arachidonic acid. Sphingomyelin architecture departs: its backbone is sphingosine, containing long-chain amino alcohol with double bond, where fatty acid attaches at amino group at C2 through N-amide bond formed by ceramide synthase in ER, producing ceramide intermediate. This amide bond affords additional hydrogen bond donor and acceptor, raising melting temperature and strengthening interaction with cholesterol's hydroxyl through hydrogen bonding network, favoring liquid-ordered domains resistant to detergent extraction. After ceramide formation, phosphocholine is transferred from phosphatidylcholine to ceramide's C1 hydroxyl by sphingomyelin synthase, creating phosphodiester linkage shared with phosphoglycerides but distinct acyl linkage. Therefore presence of amide bond fundamentally distinguishes sphingomyelin, influencing its metabolic stability, raft partitioning, and role as source for bioactive ceramide upon sphingomyelinase action during stress signaling.

Ref: Lodish et al., Molecular Cell Biology, 9th ed., Chapter 10: Sphingomyelin Structure, Amide Linkage.