Fatty acid acylation

Fatty acid acyl haHdes react with sulfamic acid (29). 

Transport of Fatty Acid Acyl Groups into the Mitochondrial Matrix 113... 

Mammalian proteins are the targets of a wide range of covalent modification processes. Modifications such as glycosylation, hydroxylation, and fatty acid acylation introduce new structural features into newly synthesized proteins that tend to persist for the lifetime of the protein. Among the covalent modifications that regulate protein function (eg, methylation, adenylylation), the most common by far is phosphorylation-dephos-phorylation. Protein kinases phosphorylate proteins by... 

Acetyl-CoA carboxylase is an allosteric enzyme and is activated by citrate, which increases in concentration in the well-fed state and is an indicator of a plentiful supply of acetyl-CoA. Citrate converts the enzyme from an inactive dimer to an active polymeric form, having a molecular mass of several milhon. Inactivation is promoted by phosphorylation of the enzyme and by long-chain acyl-CoA molecules, an example of negative feedback inhibition by a product of a reaction. Thus, if acyl-CoA accumulates because it is not esterified quickly enough or because of increased lipolysis or an influx of free fatty acids into the tissue, it will automatically reduce the synthesis of new fatty acid. Acyl-CoA may also inhibit the mitochondrial tricarboxylate transporter, thus preventing activation of the enzyme by egress of citrate from the mitochondria into the cytosol. 

Staudinger ligation techniques also can be used to detect post-translational modification of proteins in vivo. Hang et al. (2007) developed a method to monitor fatty acid acylation of proteins using azido-fatty acids fed to cells. The two major types of fatty acid acylation,... 

One major pathway leads from acetyl-CoA to the activated fatty acids (acyl-CoA for details, see p.l68). Fats, phospholipids, and glycolipids are synthesized from these, and fatty acid derivatives in particular are formed. Quantitatively, this is the most important pathway in animals and most plants. 

The elongation of the fatty acid by fatty acid synthase concludes at Cie, and the product, palmitate (16 0), is released. Unsaturated fatty acids and long-chain fatty acids can arise from palmitate in subsequent reactions. Fats are finally synthesized from activated fatty acids (acyl CoA) and glycerol 3-phosphate (see p. 170). To supply peripheral tissues, fats are packed by the hepatocytes into lipoprotein complexes of the VLDL type and released into the blood in this form (see p. 278). 

A simple approach for lipidation of peptides with di-fatty acid substituted glycerol moieties is based on the use of glyceric acid.119" For this purpose (2i )-glyceric acid is esterified at the two hydroxy groups with fatty acid acyl chlorides and the resulting lipophilic synthon (18) is used directly as an active ester, e.g. Pfp ester, to acylate selected amino groups of peptides, or is used to acylate suitably functionalized spacers. 

Fatty acids Acyl-CoA synthetase + Acyl-CoA oxidase... 

Heinemann L, Sinha K, Weyer C, Loftager M, Hirschberger S, Heise T. Time-action profile of the soluble, fatty acid acylated, long-acting insulin analogue NN304. Diabet Med 1999 16(4) 332-8. 

Lipid moieties can impart good stability to polymeric micelles since the presence of two fatty acid acyls increases the hydrophobic interactions between polymeric chains in the micelle core. Indeed, no dissociation into individual polymeric chain was observed upon the chromatography of serial dilutions of diacyllipid-PEO conjugates (Trubetskoy and Torchilin, 1995). 

Chekhonin, V., et al. 1991. Fatty acid acylated Fab-fragments of antibodies to neurospecific proteins as carriers for neuroleptic targeted delivery in brain. FEBS Lett 287 149. 

Slepnev, V., et al. 1995. Fatty acid acylated peroxidase as a model for the study of interactions of hydrophobically-modified proteins with mammalian cells. Bioconjug Chem 6 608. 

Fatty acid biosynthesis. Activated as its coenzyme A thioester, the growing fatty acid (acyl-CoA) acylates malonyl-CoA in a malonic ester synthesis. Two carbon atoms are added, with the third lost as C02. Enzymatic reduction, dehydration, and further reduction gives a fatty acid that has been lengthened by two carbon atoms. 

Question Which of the following lipids are amphiphilic fatty acids acylate ions TAGS cholesterol phosphoglycerides phosphosphingolipids glycosphingolipids ... 

COR = fatty acid acyl group -COR = arachidonoyl group... 

Fujiyama, A., Tsunasawa, S., Tamanoi, F., and Sakiyama, F. (1991). S-famesylation and methyl esterification of C-terminal domain of yeast RAS2 protein prior to fatty acid acylation. J Biol Chem 266 17926-17931. 

Membranes exhibit a common stmcture, with lipid molecules arranged in the form of one or more bilayers, or lamellae. Since lipids are generally nonfluo-rescent, lipid-bound fluorophores are an excellent tool to study this environment. These membrane probes are poorly soluble in water, and hence they partition readily into the hydrophobic regions of the membranes. The derivatives of anthroyloxy fatty acids (AF), with the fluorophore 9-anthroic acid esterfied to the 2, 6,9, 12, or 16 position along a fatty acid acyl chain (stearic acid or palmitic acid), are frequently used. The stmcture of an AF probe is shown schematically in Fig. 1... 

These same AF probes have been widely used to study the bilayer stmcture in a variety of lipid membranes [8-12]. Since the fluorophore is attached at a known position along a fatty acid acyl chain, AF probes have been used to evaluate bilayer stmctures as a function of depth. When partitioned into a membrane, the fluorophore is localized deeper in the bilayer as its attachment site to the fatty acid is moved further away from the carboxyl... 

Kabanov AV, Ovcharenko AV, Melik-Hubai ov NS, Bannikov AI, Alakliov V, Kiselev VI, Sveslmikov PG, Kiselev 01, Levashov AV, Seveiin ES (1989b) Fatty acid acylated antibodies against virus suppress its reproducdon in cells. FEBS Lett 250 238—240. 

I glycoprotein, glycoproteins Ib, IX and IV, P-selectin and alpha subunits of G proteins have been demonstrated unequivocally as S-fatty acid acylated platelet proteins (100). 

Robert S, Domurado D, Thomas D, Chopineau J (1993) Fatty acid acylation of RNase A using reversed micelles as microreactors. Biochem Biophys Res Commun 196 447 54. 

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