Saturated fatty acid amides

The natural fatty acid amides are mixtures of saturated fatty acid amides and unsaturated fatty acid amides. The present invention is based on the fact that the unsaturated fatty acid amides can be isolated very easily from a mixture of fatty acid amides by treating the fatty acid amides with urea or thiourea. The unsaturated fatty acid amides have more effective biological activity. 

Based on the above background, a new full saturated fatty acid amide (having a very low iodine number) was introduced as slip agent, which allows avoidance of the above mentioned problems with ozone, UV, or thermal degradation. ... 

Release agents erucamide, N,N -dioleoylediylenediamine, oleyl palmitamide, poly(vinyl acetate/vinyl N-octadecylcarbamate), rice bran w, saturated fatty acid amides, stearyl erucamide... 

Saturated hydrocarbons (waxes), fatty acids, metal soaps, fatty acid amides and esters (primarily Cig-Cis) act as internal lubricants, fluoro elastomers as external lubricants. Many other polymer additives, e.g. antistatic agents, antifogs, antioxidants, UV stabilisers, etc., act as lubricants in the barrel of the extruder once they are in the liquid form. 

Fig. 4.2. The effect of chain length (li) on the degree of hydrolysis [%] of primary amides by rat liver preparations (5 h at pH 7.4). Black bars amides of normal saturated fatty acids hatched bar isohexanamide unshaded bars amides of m-phenyl-substituted saturated fatty...

Gly-Asn-Glu-Ala-Ser-Tyr-Pro-Leu-Glu-Hsl Assuming that the blocking group X is linked to the NH -terminal glycine by the usual amide bond, then hydrolysis should yield a carboxylic acid = 228. This corresponds to the of a C saturated fatty acid, the mass spectra are consistent with the supposition that X is C H CO-. This possibility was confirmed by... 

The UV absorption of the peptide bond, —NH—CO—, is centered around 210 nm. Its molar absorption coefficient, approx. 3 x 10, is much higher than that of the amide group of saturated fatty acids at the same wave length, a consequence of the mesomeric electron-distribution (partial double bond character) of the —NH—CO— moiety. 

Slip agents such as saturated and unsaturated fatty acid amides can overcome film surface friction. These agents migrate to the film surface dining processing and upon aging at elevated temperatures (see Release Agents). 

The slip additives employed in most commercial films are relatively high molecular weight fatty acid amides. The most widely used fatty acid amides are erucamide, an unsaturated 22 carbon amide (13-docosenamide), and behenamide (docosanamide), the saturated analogue of emcamide. Both of these compounds are readily available, naturally occurring materials. They are normally provided as mixtures containing a small amount of other amides having about 18 to 20 carbons. ... 

A number of amide- and ester-linked fatty acids and (/ )-3-hydroxy acids are components of the lipid A part in the LPS from Gram-negative bacteria. The acids have been tabulatedand the chemistry of lipid A summarized. The most common acids in lipid A from Enterobacteriaceae are the saturated 12 0,14 0, and 16 0, and the (/ )-3-hydroxy-14 0, The last is linked to N-2 and 0-3 of the 2-amino-2-deoxy-D-glucopyranosyl residues, and the others are ester-linked to the hydroxy acid, as in the lipid A (44) of Salmonella minnesota. Other linear and branched fatty acids, unsaturated acids, S)-2- and (/ )-3-hydroxy acids, and 3-oxotetradecanoic acid are components of lipid A from certain different species. In the lipid A from Rhizobium trifolii, 2,7-dihydroxyoctanoic acid is linked as amide to a 2-amino-2-deoxy-D-gl ucopy ranosy 1 residue. ... 

N-Myristoylation is achieved by the covalent attachment of the 14-carbon saturated myristic acid (C14 0) to the N-terminal glycine residue of various proteins with formation of an irreversible amide bond (Table l). 10 This process is cotranslational and is catalyzed by a monomeric enzyme called jV-myri s toy 11ransferase. 24 Several proteins of diverse families, including tyrosine kinases of the Src family, the alanine-rich C kinase substrate (MARKS), the HIV Nef phosphoprotein, and the a-subunit of heterotrimeric G protein, carry a myr-istoylated N-terminal glycine residue which in some cases is in close proximity to a site that can be S-acylated with a fatty acid. Functional studies of these proteins have shown an important structural role for the myristoyl chain not only in terms of enhanced membrane affinity of the proteins, but also of stabilization of their three-dimensional structure in the cytosolic form. Once exposed, the myristoyl chain promotes membrane association of the protein. 5 The myristoyl moiety however, is not sufficiently hydrophobic to anchor the protein to the membrane permanently, 25,26 and in vivo this interaction is further modulated by a variety of switches that operate through covalent or noncovalent modifications of the protein. 4,5,27 In MARKS, for example, multiple phosphorylation of a positively charged domain moves the protein back to the cytosolic compartment due to the mutated electrostatic properties of the protein, a so-called myristoyl-electrostatic switch. 28 ... 

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