Fatty acid characterization

Kurtzhals P, Havelund S, Jonassen I, Kiehr B, Larsen UD, Ribel U et al. Albumin binding of insulins acylated with fatty acids characterization of the ligand-protein interaction and correlation between binding affinity and timing of the insulin effect in vivo. Biochem J 1995 312(Pt 3) 725-731. 

There are many unsaturated fatty acids, characterized by having an alk-ene unit or diene or polyene units in the long carbon chain rather than the alkane chain found in 92-95. Common unsaturated fatty acids are palmitoleic acid (96 C16), oleic acid (97 C18), linolenic acid (98 C18), a-linolenic acid (99 C18), and y-linolenic acid (100 C18). Other examples include arachidonic acid (101 C20), erucic acid (102 C22— found in mustard seed), and nervonic acid (103 C24— important for the biosynthesis of nerve cell myelin). 

Transmission electron microscopy (TEM) can resolve features down to about 1 nm and allows the use of electron diffraction to characterize the structure. Since electrons must pass through the sample however, the technique is limited to thin films. One cryoelectron microscopic study of fatty-acid Langmuir films on vitrified water [13] showed faceted crystals. The application of TEM to Langmuir-Blodgett films is discussed in Chapter XV. 

Animal fats and vegetable oils are triacylglycerols, or triesters, formed from the reaction of glycerol (1,2, 3-propanetriol) with three long-chain fatty acids. One of the methods used to characterize a fat or an oil is a determination of its saponification number. When treated with boiling aqueous KOH, an ester is saponified into the parent alcohol and fatty acids (as carboxylate ions). The saponification number is the number of milligrams of KOH required to saponify 1.000 g of the fat or oil. In a typical analysis, a 2.085-g sample of butter is added to 25.00 ml of 0.5131 M KOH. After saponification is complete, the excess KOH is back titrated with 10.26 ml of0.5000 M HCl. What is the saponification number for this sample of butter ... 

Three generations of latices as characterized by the type of surfactant used in manufacture have been defined (53). The first generation includes latices made with conventional (/) anionic surfactants like fatty acid soaps, alkyl carboxylates, alkyl sulfates, and alkyl sulfonates (54) (2) nonionic surfactants like poly(ethylene oxide) or poly(vinyl alcohol) used to improve freeze—thaw and shear stabiUty and (J) cationic surfactants like amines, nitriles, and other nitrogen bases, rarely used because of incompatibiUty problems. Portiand cement latex modifiers are one example where cationic surfactants are used. Anionic surfactants yield smaller particles than nonionic surfactants (55). Often a combination of anionic surfactants or anionic and nonionic surfactants are used to provide improved stabiUty. The stabilizing abiUty of anionic fatty acid soaps diminishes at lower pH as the soaps revert to their acids. First-generation latices also suffer from the presence of soap on the polymer particles at the end of the polymerization. Steam and vacuum stripping methods are often used to remove the soap and unreacted monomer from the final product (56). 

Amides can be titrated direcdy by perchloric acid ia a nonaqueous solvent (60,61) and by potentiometric titration (62), which gives the sum of amide and amine salts. Infrared spectroscopy has been used to characterize fatty acid amides (63). Mass spectroscopy has been able to iadicate the position of the unsaturation ia unsaturated fatty amides (64). Typical specifications of some primary fatty acid amides and properties of bisamides are shown ia Tables 5 and 6. 

Although vegetable oils and animals fats were commonly used in ancient times, most higher acids were not known until the beginning of the nineteenth century. Then the nature of the naturally occurring 18-carbon fatty acids was estabHshed, and hundreds of long-chain fatty acids have been isolated from natural sources and characterized. 

Oils are mixtures of mixed esters with different fatty acids distributed among the ester molecules. Generally, identification of specific esters is not attempted instead the oils are characterized by analysis of the fatty acid composition (8,9). The principal methods have been gas—Hquid and high performance Hquid chromatographic separation of the methyl esters of the fatty acids obtained by transesterification of the oils. Mass spectrometry and nmr are used to identify the individual esters. It has been reported that the free fatty acids obtained by hydrolysis can be separated with equal accuracy by high performance Hquid chromatography (10). A review of the identification and deterrnination of the various mixed triglycerides is available (11). 

Atherosclerosis is a degenerative disease which is characterized by cholesterol-containing thickening of arterial walls. Saturated fatty acids, high levels of cholesterol, elevated blood pressure, and elevated serum lipoprotein are well-knowm risk... 

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. 

FATP5 KO mice have been characterized in two studies focusing on the role of FATP5 in hepatic lipid and bile metabolism. LCFA uptake in primary hepato-cytes isolated from FATP5 KO mice was reduced by 50% and hepatic lipid content in the KO mice was significantly reduced despite an increased fatty acid de novo biosynthesis. Detailed analysis of the hepatic lipidome of FATP5 KO mice revealed significant... 

Most of these enzymes have steroids or fatty acids as their substrates (Table 1). Many P450s in endogenous biotransformation pathways are characterized by usually very narrow substrate and product specificity and by tight regulatory systems, especially those involved in steroid hormone biosynthesis. 

Guidon, P.T. Hightower, L.E. (1986). Purification and initial characterization of the 71-kilodalton rat heat-shock protein and its cognate as fatty acid binding proteins. Biochemistry, 25, 3231-9. 

Interest in import of proteins into peroxisomes has been stimulated by studies on Zellweger syndrome. This condition is apparent at birth and is characterized by profound neurologic impairment, victims often dying within a year. The number of peroxisomes can vary from being almost normal to being virtually absent in some patients. Biochemical findings include an accumulation of very long chain fatty acids, abnormalities of... 

Pedrotta V, B Witholt (1999) Isolation and characterization of the cw/fra 5-unsaturated fatty acid isomerase of Pseudomonas oleovorans Gpol2. J Bacteriol 181 3256-3261. 

Craft DL, KM Madduri, M Eshoo, CR Wilson (2003) Identification and characterization of the CYP52 family of Candida tropicalis ATCC 20336, important for the conversion of fatty acids and alkanes to a,(o-dicarboxylic acids. Appl Environ Microbiol 69 5983-5991. 

Essential fatty acid deficiency Deficiency of linoleic acid, linolenic acid, and/or arachidonic acid, characterized by hair loss, thinning of skin, and skin desquamation. Long-chain fatty acids include trienes (containing three double-bonds [e.g., 5,8,11-eicosatrienoic acid, or Mead acid trienoic acids) and tetraenes (containing four doublebonds [e.g., arachidonic acid]). Biochemical evidence of essential fatty acid deficiency includes a trieneitetraene ratio greater than 0.4 and low linoleic or arachidonic acid plasma concentrations. 

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