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The Chemical Synthesis of D-Glucuronic Acid - …

hyaluronan, sodium hyaluronate) is a polysaccharide, made by animals and some bacteria, with long chains made of N-acetyl-D-glucosamine alternating with glucuronic acid.

Idraparinux, the fully O-sulfated, O-methylated, heparin-related pentasaccharide possessing selective factor Xa inhibitory activity, was prepared by a new synthetic pathway. This route was based on a [2+3] block synthesis utilizing a 6-O-silyl-protected l-idose-containing trisaccharide acceptor, which was glycosylated with a disaccharide donor containing a non-oxidized precursor of the glucuronic acid. The unique strategy of multiple functionalizations at pentasaccharide levels, involving triple methylation followed by oxidation of the glucose and the idose precursors into d-glucuronic and l-iduronic acids in one step, proved to be highly efficient, providing the target pentasaccharide through a 39-step synthesis starting from d-glucose and methyl α-d-glucopyranoside.

Measurement of uridine diphosphate glucuronic acid concentrations and synthesis in animal tissues

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Glucuronic acid (GA) is an organic acid which was first isolated in urine (hence the root name)

One male volunteer excreted 26% of a 4000-mg oral dose of phenethyl alcohol (No. 987) in his urine as phenylacetylglutamine within 24 h (Thierfelder & Schempp, 1917). In rabbits, 42% and 5% of a single 300 mg/kg bw oral dose of phenethyl alcohol was excreted in the urine as glycine and glucuronic acid conjugates, respectively, of phenylacetic acid within 24 h. The ether-soluble acid extracted from the 24-h urine accounted for 61% of the dose (Bray et al, 1958). In an earlier study, 53% of a dose of 1300 mg bw of phenylacetic acid administered to rabbits by gavage was isolated from the 24-h urine as an ether-soluble acid. No appreciable quantity (

AB - Idraparinux, the fully O-sulfated, O-methylated, heparin-related pentasaccharide possessing selective factor Xa inhibitory activity, was prepared by a new synthetic pathway. This route was based on a [2+3] block synthesis utilizing a 6-O-silyl-protected l-idose-containing trisaccharide acceptor, which was glycosylated with a disaccharide donor containing a non-oxidized precursor of the glucuronic acid. The unique strategy of multiple functionalizations at pentasaccharide levels, involving triple methylation followed by oxidation of the glucose and the idose precursors into d-glucuronic and l-iduronic acids in one step, proved to be highly efficient, providing the target pentasaccharide through a 39-step synthesis starting from d-glucose and methyl α-d-glucopyranoside.

Glucuronic acid (from Ancient Greek ..

Phenoxyacetic acid was fed to male rabbits at a dose of 100–200 mg/kg bw, and some animals also received glycine in amounts corresponding to three equivalents of the acid. In this test, 44–72% of the phenoxyacetic acid was recovered unchanged in the urine within 6 h and 82–105% within 24 h. There was no evidence of conjugation with either glucuronic acid or glycine, even when the diet was supplemented with glycine. A rabbit that received an oral dose of 500 mg of the glycine conjugate of phenoxyacetic acid excreted 30% of the dose unconjugated in the urine after 18 h (Levey & Lewis, 1947). In another study, 55% of an oral dose of an unspecified amount of phenoxyacetic acid was recovered in the urine of dogs and 61% in the urine of humans. No evidence for glycine or glucuronic acid conjugation was found (Thierfelder & Schempp, 1917).

Protecting Groups for Glucuronic Acid: Application to the Synthesis of New Paclitaxel (Taxol) Derivatives.

N2 - Idraparinux, the fully O-sulfated, O-methylated, heparin-related pentasaccharide possessing selective factor Xa inhibitory activity, was prepared by a new synthetic pathway. This route was based on a [2+3] block synthesis utilizing a 6-O-silyl-protected l-idose-containing trisaccharide acceptor, which was glycosylated with a disaccharide donor containing a non-oxidized precursor of the glucuronic acid. The unique strategy of multiple functionalizations at pentasaccharide levels, involving triple methylation followed by oxidation of the glucose and the idose precursors into d-glucuronic and l-iduronic acids in one step, proved to be highly efficient, providing the target pentasaccharide through a 39-step synthesis starting from d-glucose and methyl α-d-glucopyranoside.

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Glucuronic acid - an overview | ScienceDirect Topics


The first steps are identical to those of glycogen synthesis, ..

Disaccharide building blocks, featuring a disarmed glucuronic acid donor moiety and a di-tert-butylsilylidene-protected glucosamine part, were used in the rapid and efficient assembly of HA fragments up to the pentadecamer level, equipped with a conjugation-ready anomeric allyl function.

Protecting Groups for Glucuronic Acid: Application to …

Phenethyl alcohol is successively oxidized to phenylacetaldehyde and phenylacetic acid in vivo Phenylacetic acid undergoes species-specific conjugation with a variety of amino acids, amines or glucuronic acid, followed by excretion almost exclusively in the urine (James et al., 1972; see Figure 2). Phenethyl alcohol is readily oxidized to phenylacetaldehyde by an assortment of NAD+-dependent alcohol and aldehyde dehydrogenases (Bosron & Li, 1980). The greatest activity of mammalian alcohol dehydrogenases (ALDH) occurs in the liver, where they show broad substrate specificity for the oxidation of primary aliphatic and aromatic alcohols. Human liver ALDH showed a decreased Michaelis-Menten constant (Km, the concentration of the specific substrate at which a given enzyme yields one-half its maximum velocity with increasing lipophilicity); however, the maximum rate or velocity of an enzymatic reaction which is indicative of all the enzyme active site(s) complexed with substrate, Vmax, remained essentially constant, suggesting that the rate-limiting step does not involve the binding or release of the alcohol or aldehyde intermediate (Pietruszko et al., 1973).

Protecting Groups for Glucuronic Acid: ..

Although phenylacetic acid has been studied extensively, investigations conducted before 1950 on human metabolism (Shiple & Sherwin, 1922; Power & Sherwin, 1927; Ambrose et al.,1933; Wagreich et al.,1940) failed to account for the endogenous level of 250–500 mg/kg per day of phenylacetic acid conjugated with glutamine (Stein et al., 1954) present in human urine and did not adequately characterize the array of urinary conjugates that were formed from phenylacetic acid. More recent work demonstrates that conjugation is both dose-dependent and species-specific. The major metabolic options available to phenyl acetic acid are conjugation with glucuronic acid, glycine, taurine or glutamine and elimination as the free acid.

Uridine diphosphate glucuronic acid - Wikipedia

Treick, R.W. & Konetzka, W.A. (1964) Physiological state of and the inhibition of deoxyribonucleic acid synthesis by phenethyl alcohol. ., 88, 1580–1584.

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