Hydrophobic groups fatty acids

Vesicles are usually derived from hydrophobic oligomeric chains that are terminated by a hydrophilic end group. Fatty acids are the prototypical molecules that form double... 

Lipid bilayer Ordered double layer of phospholipid molecules arranged so that the hydrophilic heads (phosphate groups) are on the outside and the hydrophobic tails (fatty-acid chains) are on the inside facing each other. 

Certain fatty acids (primarily myristic and palmitic acids) are covalently attached to a wide variety of eukaryotic proteins. Such proteins are referred to as acylated proteins. Fatty acid groups (called acyl groups) clearly facilitate the interactions between membrane proteins and their hydrophobic environment. Fatty acids are transported from fat cells to body cells esterified to serum proteins and enter cells via acyl transfer reactions. Some of the acylated proteins in cells... 

Biosurfactants are classified based on their chemical composition and microbial origin. The chemical structure of biosurfactants contains hydrophilic and hydrophobic groups. Amino acids, peptides and polysaccharides can be present as hydrophilic moieties and saturated or unsaturated fatty acids can be present as hydrophobic moieties in the structure. Structure based classification has following major classes of biosurfactants (Guerra-Santos et al., 1987 Kooper and Goldenberg, 1987) (i) Glycolipids (Rhamnolipids, Trehalolipids and Sophorolipids) (ii) Lipopeptide and lipoprotein (iii) Fatty acids, phospholipids and neutral lipids (iv) Pol5mieric biosurfactants, and (v) Particulate biosurfactants. 

Figure C2.4.1. Schematic diagram of a fatty acid witir a hydrophiiic (COO ) and a hydrophobic end group (CH ) (ieft) and of an amphiphiie in generai (right).

A typical biomembrane consists largely of amphiphilic lipids with small hydrophilic head groups and long hydrophobic fatty acid tails. These amphiphiles are insoluble in water (<10 ° mol L ) and capable of self-organization into uitrathin bilaycr lipid membranes (BLMs). Until 1977 only natural lipids, in particular phospholipids like lecithins, were believed to form spherical and related vesicular membrane structures. Intricate interactions of the head groups were supposed to be necessary for the self-organization of several ten thousands of... 

A Acylsarcosinates. Sodium A/-lautoylsarcosinate [7631-98-3] is a good soap-like surfactant. Table 4 gives trade names and properties. The amido group in the hydrophobe chain lessens the interaction with hardness ions. A/-Acylosarcosinates have been used in dentifrices (qv) where they ate claimed to inactivate enzymes that convert glucose to lactic acid in the mouth (57). They ate prepared from a fatty acid chloride and satcosine ... 

Carboxylic Acid Esters. In the carboxyflc acid ester series of surfactants, the hydrophobe, a naturally occurring fatty acid, is solubilized with the hydroxyl groups of polyols or the ether and terminal hydroxyl groups of ethylene oxide chains. 

The hydrophilic nature of the carboxyl group balanced against the hydrophobic nature of the hydrocarbon chain allows long-chain fatty acids to form monomolecular films at aqueous Hquid-gas, Hquid—Hquid, or Hquid—soHd interfaces (18). 

Amphipathic lipids spontaneously form a variety of structures when added to aqueous solution. All these structures form in ways that minimize contact between the hydrophobic lipid chains and the aqueous milieu. For example, when small amounts of a fatty acid are added to an aqueous solution, a mono-layer is formed at the air-water interface, with the polar head groups in contact with the water surface and the hydrophobic tails in contact with the air (Figure 9.2). Few lipid molecules are found as monomers in solution. 

Further addition of fatty acid eventually results in the formation of micelles. Micelles formed from an amphipathic lipid in water position the hydrophobic tails in the center of the lipid aggregation with the polar head groups facing outward. Amphipathic molecules that form micelles are characterized by a unique critical micelle concentration, or CMC. Below the CMC, individual lipid molecules predominate. Nearly all the lipid added above the CMC, however, spontaneously forms micelles. Micelles are the preferred form of aggregation in water for detergents and soaps. Some typical CMC values are listed in Figure 9.3. 

Bistline and Stirton compared the CMC values of ester sulfonates with cyclic ester groups [54]. The phenyl esters have higher values than benzyl and cyclohexyl esters. The influence of the structure of the ester group decreases with increasing chain length of the hydrophobic fatty acid group. The cyclic esters of a-sulfostearic acid, for example, have nearly the same CMC values. 

The alkaline product from the wood ash was a crude solution of sodium and potassium carbonates called "lye". On boiling the vegetable oil with the lye, the soap (sodium and potassium salts of long chained fatty acids) separated from the lye due to the dispersive interactions between the of the fatty acid alkane chains and were thus, called "lyophobic". It follows that "lyophobic", from a physical chemical point of view, would be the same as "hydrophobic", and interactions between hydrophobic and lyophobic materials are dominantly dispersive. The other product of the soap making industry was glycerol which remained in the lye and was consequently, termed "lyophilic". Thus, glycerol mixes with water because of its many hydroxyl groups and is very polar and hence a "hydrophilic" or "lyophilic" substance. 

Figure 41-3. Diagrammatic representation of a phospholipid or other membrane lipid. The polar head group is hydrophilic, and the hydrocarbon tails are hydrophobic or lipophilic. The fatty acids in the tails are saturated (S) or unsaturated (U) the former are usually attached to carbon 1 of glycerol and the latter to carbon 2. Note the kink in the tail of the unsaturated fatty acid (U), which is important in conferring increased membrane fluidity.

Step 2 - A patch pipet is removed from the solution, the polar head groups of the monolayer lipids are adsorbed to the interface while the fatty acid hydrophobic tails are exposed to the air ... 

Micelles are the simplest possible structures. These are spherical entities in which the hydrophobic groups are directed towards the interior. Micelle formation occurs preferentially when the head groups are larger than the hydrophobic groups, as in fatty acids. 

Phospholipids are the most important of these liposomal constituents. Being the major component of cell membranes, phospholipids are composed of a hydrophobic, fatty acid tail, and a hydrophilic head group. The amphipathic nature of these molecules is the primary force that drives the spontaneous formation of bilayers in aqueous solution and holds the vesicles together. 

Figure 22.3 The basic construction of phosphodiglyceride molecules within lipid bilayers. The fatty acid chains are embedded in the hydrophobic inner region of the membrane, oriented at an angle to the plane of the membrane surface. The hydrophilic head group, including the phosphate portion, points out toward the hydrophilic aqueous environment.

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