Carbohydrate fatty acid ester

The selective enzyme-catalyzed acylation of carbohydrates is of great interest, as of carbohydrates fatty acid esters of carbohydrates have important applications in detergents, cosmetics, foodstuff, and pharmaceuticals because of their surface-active properties. Monoacylated sugars have been synthesized by lipase-catalyzed transesterifications of activated esters in pyridine and by protease-catalyzed esterifications in DMF. A most remarkable new development... 

Activity and Selectivity of Proteases in Synthesis of Carbohydrate Fatty Acid Esters... 

In the pharmaceutical field, oleic acid is used in several circumstances, being widely used for the production of monoolein (Wang et al., 2013), carbohydrate fatty acid esters (Abdulmalek et al., 2012), phytosteryl esters of fatty acids (Pan et al., 2012) and fatty acid esters of vitamin C (Stojanovic et al., 2013), which will be mentioned below. This is in addition to other applications, to a lesser extent, such as dopamine, a phenolic compound derived from tyrosine and belonging to the catecholamine family that has been shown to be an effective scavenger of superoxide and hydroxyl radicals (Sellami et al., 2013) and prodrugs, compounds that suffer biotransformation before presenting pharmacological effects (Arouri et al., 2013). 

Degn, R, and W. Zimmermann. 2001. Optimization of Carbohydrate Fatty Acid Ester Synthesis in Organic Media by a Lipase from Candida Antarctica Biotechnology and Bioengineering 74 (6) 483-491. 

In polymer applications derivatives of oils and fats, such as epoxides, polyols and dimerizations products based on unsaturated fatty acids, are used as plastic additives or components for composites or polymers like polyamides and polyurethanes. In the lubricant sector oleochemically-based fatty acid esters have proved to be powerful alternatives to conventional mineral oil products. For home and personal care applications a wide range of products, such as surfactants, emulsifiers, emollients and waxes, based on vegetable oil derivatives has provided extraordinary performance benefits to the end-customer. Selected products, such as the anionic surfactant fatty alcohol sulfate have been investigated thoroughly with regard to their environmental impact compared with petrochemical based products by life-cycle analysis. Other product examples include carbohydrate-based surfactants as well as oleochemical based emulsifiers, waxes and emollients. 

The synthesis of long-chain fatty acid esters of carbohydrates is inherently more demanding. It was found that glucose did not react with vinyl laurate in a pure ionic liquid medium, but in biphasic tert-butyl alcohol/[BMIm][PF6], glucose could be acylated by the vinyl esters of O, 2-Cu, fatty acids. The best results were obtained with CaLB, which was twice as active as TIL, and the selectivity for acylation at C-6 was high [114]. The esterification of glucose with palmitic acid, which is, in an industrial context, to be preferred over transesterification, has recently been demonstrated in tert-butyl alcohol/[BMIm][PF6] medium [115]. 

T Polat, HG Bazin, RJLinhardt. Enzyme catalyzed regioselective synthesis of sucrose fatty acid ester surfactants. J Carbohydr Chem 16 1319-1325, 1997. 

About 3000 plant species are known to release HCN from their tissues, a process which is known as cyanogenesis[17, 181. Storage compounds are cyanohydrins where the hydroxy function is glycosylated to a carbohydrate or protected as a fatty acid ester. The plant defence mechanism in the case of sugar compounds is a two-step reaction. Initially a glycosidase liberates the cyanohydrin moiety, which is cleaved either spontaneously by base catalysis or enzymatically by the action of oxynitrilases to release the corresponding carbonyl compound and HCN1191. 

Bengazoles contain a carbohydrate like polyol side chain together with a fatty acid ester. Both 1190a and 1190b are potent antihelminthic agents. 

Sugar (glucose) fatty acid esters Fatty acids Carbohydrates Pharmaceutical, cosmetic, and food industry Ganske and Bomscheuer (2005)... 

In the pharmaceutieal area, the reaction of oleic acid catalyzed by lipase is used for the production of monoolein and carbohydrate fatty aeid esters, compounds with emulsifiers and surfactant properties (Wang et al., 2013 Abdulmalek et al., 2012). Another important surfactant produced is the fatty acid ester of vitamin C (Stojanovic et al., 2013). Enzymatic synthesis of aseorbyloleate is very attractive, as well as surfactants, which have high antioxidant potential (Viklrmd Alander Hult, 2003). Due to biological... 

The preparation of polymeric materials from renewable resources is of great economic and ecological significance. Oils and fats are one of the most important renewable materials since they offer a large number of possibilities for application that can be rarely met by petrochemistry. Although the hydrosilylation of olefins has been widely studied, a few reports have appeared on the fatty acid esters (4). Carbohydrate-modified polysiloxanes are another very important group of hybrid materials. Some examples of such modified, comb-structured polysiloxanes and also a few examples of carbohydrate-segmented polydimethylsiloxane block copolymers have been described. Hydrosilylation has also been used for the synthesis of silylated polycarbonates or polycarbonate-disiloxane-polycarbonate triblock copolymers. 

Figure 1. Chemical structures of lipid A-diphosphate (A) and two antagonistic lipid A-diphosphate molecules, (B and C). Lipid A-diphosphate from E. coli is a 1,4-di-phosphorylated P-1,6-linked D-glucosamine disaccharide with four residues of amide-and esterified R-(-)-3-hydroxy fatty acids ( denotes the chiral centers in the hydroxy fatty-acid esters, apart form the chiral and epimeric carbons in the disaccharide moieties which are not marked). The antagonistic lipid A-diphosphate molecules shown in (B) and (C) contain the same disaccharide as in (A) however, they differ in the number anchored carbohydrate positions and the number of chiral fatty-acid chains but the chain lengths is the same (C J. The corresponding monophosphate of lipid A is only phosphorylated at the reducing end of the disaccharide.

These points apply also to the subset of carbohydrate-based surfactants that comprises a fatty acid hydrophobic group attached to a sugar-based head group, sugar fatty acid esters. 

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