Glycidol phosphate

Example 12 dibenzyl-iV,iSr-diisopropylphosphoroamidite has been applied by Lindberg et al. in the efficient synthesis of phospholipids from glycidol phosphates [39]. 

Carbohydrate Systems Carbohydrate binding sites, 46, 362 glu-cosidases, 46, 368 glycidol phosphates and 1,2-anhydrohexitol 6-phosphates, 46, 381 /3-galactosidase, 46, 398 lysozyme, 46, 403. 

Compound V or glycidol phosphate was used by Rose and O Connell (1969) to study muscle triosephosphate isomerase because it closely resembles the presumed ene-diol intermediate in this enzyme s reaction mechanism. Coincidentally, it also proved to be an effective inhibitor of enolase even though it is not closely analogous to substrates of this enzyme. The structure of glycidol phosphate is similar to phosphononomycin (DC), an antibiotic isolated from fermentation broths of Streptomyces fradiae (Christensen et al. 1969). 

Glycidol phosphate was synthesized by phosphorylation of commercially available glycidol with POCI3 in trimethylphosphate with added... 

Based on the pH dependency of the inactivation rate of rabbit muscle triosephosphate isomerase with glycidol phosphate, the pK for Glu-165 was calculated to be less than 5.5 in one study and 6.0 in another. Since this difference could be due to the complication of a variable affinity of the reagent for the enzyme as a result of the change in ionization state of the reagent over the pH range examined, the pH dependency of inactivation rate was also studied with the strong, monoprotic acid chloroacetol sulfate, another compound which selectively esterifies Glu-165. With this compound, the pK of Glu-165 in the rabbit muscle enzyme was found to be less than 5.0. An exact value could not be determined because of the instability of the enzyme to acid however, with the more stable yeast enzyme, a pKa of 3.9 was calculated. Thus, the acidity of the essential carboxyl group is consistent with its postulated role in catalysis. 

Glycidol phosphate, 144,145, 381-387 synthesis of, 382, 383 D-Glycidol phosphate, synthesis of, 387 L-Glycidol phosphate, synthesis of, 384-387... 

Propylene oxide-based glycerol can be produced by rearrangement of propylene oxide [75-56-9] (qv) to allyl alcohol over triUthium phosphate catalyst at 200—250°C (yield 80—85%) (4), followed by any of the appropriate steps shown in Figure 1. The specific route commercially employed is peracetic acid epoxidation of allyl alcohol to glycidol followed by hydrolysis to glycerol (5). The newest international synthesis plants employ this basic scheme. 

Phosphoric acid diesters are prepared by treating a liquid slurry of phosphate monoester with epoxides in the presence of alkali compounds. Thus a mixture of monolauryl phosphate sodium salt and triethyl amine in water was treated with glycidol at 80°C for 8 h to give 98% lauryl(2,3-dihydroxypropyl)phosphate sodium salt [13]. 

A mixture of monolauryl phosphate sodium salt and triethylamine in H20 was treated with glycidol at 80°C for 8 h to give 98% lauryl 2,3-dihydro-xypropyl phosphate sodium salt [304]. Dyeing aids for polyester fibers exist of triethanolamine salts of ethoxylated phenol-styrene adduct phosphate esters [294], Fatty ethanolamide phosphate surfactant are obtained from the reaction of fatty alcohols and fatty ethanolamides with phosphorus pentoxide and neutralization of the product [295]. A double bond in the alkyl group of phosphoric acid esters alter the properties of the molecule. Diethylethanolamine salt of oleyl phosphate is effectively used as a dispersant for antimony oxide in a mixture of xylene-type solvent and water. The composition is useful as an additive for preventing functional deterioration of fluid catalytic cracking catalysts for heavy petroleum fractions. When it was allowed to stand at room temperature for 1 month it shows almost no precipitation [241]. 

Preparation of the DHAP analogue, 4-hydroxy-3-oxobutylphosphonic acid, which is an effective donor substrate, is accomplished in four steps from glycidol.29 Glycidol is silyl protected then its epoxide is opened by dimethyl methylphosphonate. The secondary alcohol was oxidized under the Dess-Martin conditions. Deprotection of the alcohol followed by phosphate hydrolysis, generated the DHAP phosphonate analogue (Scheme 5.9). 

The dephosphorylation of 5-chloro and 5-bromo-D-xylulose-l-phosphate was carried out by the addition of acid phosphatase. After purification, 5-chloro-D-xylu-lose and 5-bromo-D-xylulose were recovered as pure compounds in 47 and 12% yields, respectively, from DHAP. In this study, we have shown that DHAP generated from glycidol 7 can be used in situ as a donor substrate of FruA in the presence of 2-halo-acetaldehydes 20 as acceptor substrates for the synthesis of 5-halo-D-xylulose 19. Given that DHAP aldolases display a broad specificity towards acceptor substrates, this strategy can be applied generally to the synthesis of various analogs of monosaccharides. 

Lactose (500 mg) and glycidol (1.5 mL) were dissolved in 4 mL of 0.1 M phosphate buffer, pH 7.0. j8-Galactosidase from Aspergillus oryzae (69 units. Sigma) was added. The reaction mixture was stirred at 37°C for 24 h. Analysis by thin-layer chromatography (TLC) showed a new spot with a higher Rf value than the starting materials. H NMR analysis indicated the formation of the product. The yield was estimated to be around 20% by the TLC analysis. 

Acrolein is a metabolite of allyl alcohol and cyclophosphamide, and these compounds should be considered in acrolein metabolism schemes. Allyl alcohol in the presence of nicotinamide adenine dinucleotide phosphate (NADPH) and liver or lung microsomes degrades to acrolein, acrylic acid, and glycidol. 

Hexachloro-1,3-butadiene Laurate canola oilj Methacrylic acid copolymer Nitrogen PPG-17 PPG-20 PPG-28-buteth-35 PPG-2 methyl ether Propylene carbonate Propylene glycol Propylene glycol ricinoleate Sebacic acid Sulfolane 0,0,0-Tributyl phosphorothioate Tri-m-cresyl phosphate Triethyl phosphate 0,0,0-Triisooctyl phosphorothioate Trimethylcyclohexanol Tri-p-tolyl phosphate hydraulic fluid additive 1,2-Butylene carbonate Ethylene carbonate hydraulic fluid additive, oil Glycidol... 

The availability of relatively pure MAPs allows conversion to a mixture of unsymmetrical DAPs. For example, reaction of monolauryl phosphate with a fivefold excess of dimethyl sulfate in an aqueous potassium hydroxide is reported to yield lauryl methyl phosphate in 84% yield [74], Epoxides are also popular alkylating agents. Reaction of a salt of monolauryl phosphate with ethylene oxide [75,76], epichlorohydrin [77], glycidol, or glycidol methacrylate [78] is reported to yield unsymmetrical alkyl phosphoglycol derivatives. The 3-chloro-2-hydroxypropyl ester adduct from epichlorohydrin can be further derivatized. Use of the monosodium or monopotassium salt is important in controlling selectivity to the unsymmetrical DAP. 

In an ice bath are mixed 0.5 ml of trimethylphosphate, 0.25 ml of A, iV-dimethylaniline, and 0.1 ml of POCls or POCls (1 mmole). To the stirred solution is added a mixture of 0.5 ml of trimethyl phosphate containing 0.07 ml (1 mmole) of glycidol. After 1 hr at 0°, the reaction is added dropwise to 10 ml of cold water while maintaining the pH between 5 and 9 with 2 N NaOH. After final adjustment to pH 7.0, the dimethylaniline is extracted twice with 6 ml of ether. The aqueous solution is adjusted to pH 7.5, 2 ml of 1 Af barium acetate are added, and... 

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