D,L-Glyceric acid

In the case of the oxidation of glycerol, D,L-glyceric acid has also been isolated. Hlasiwetz and Habermann treated glycerol with chlorine water and obtained the acid as the main product. From the action of bromine water on glycerol, Barth obtained glyceric acid, bromoform and carbon dioxide. In the absence of water, bromine converted glycerol to dibromohydrin and bromoacetic acid. The former decomposed to hydrogen bromide and acrolein. 

Imidazolidine derivative 9 was obtained by the borohydride reduction of the corresponding A2-imidazolinium cation precursor formed by the condensation of the acetonide of the ethyl ester of D,L-glyceric acid and 1,1-dimethyl-1,2-diamine followed by acetylation and methylation (80H947, 83T3987). 

There are fewer examples of this for such Ru-catalysed oxidations than for C-H activation, cleavage of the C-C bond in diols being the main example [111]. Optically pure D- and L-glyceric acids were made by cleavage of vicinal diols or of a-hydroxy acids by RuCl3/aq. Na(ClO) pH 8, e.g. l,2 5,6-di-0-isopropylidene-D-mannitol to 2,3-0-isopropylidene-D-glyceric acid (Fig. 4.6) [112],... 

D,L-GIyceraldehyde, III, 166 Glyceric acid, effect on conductivity of boric acid, IV, 195 reduction of, IV, 109 D-GIyceric acid, III, 21 D,L-GIyceric acid, III, 132, 167 Glycerides, trityl ethers, III, 105 —, unsaturated, II, 125 Glycerol, butyric acid from, IV, 110 effect on conductivity of boric acid, IV, 191... 

The second type of oxaluria is associated with the urinary excretion of L-glyceric acid. Hydroxypyruvate is a substrate for both D-glyceric and lactic dehydrogenases. In presence of the first it will yield D-glycerate, in presence of the second L-glycerate. 

L-glyceric aciduria urinary excretion of oxalic acid, urinary L-glyceric acid oxalate stones D-glyceric dehydrogenase deficiency Autosomal recessive Williams, H.E., and Smith, L.H., Jr. L-glyceric aciduria a new genetic variant of primary hyperoxaluria. N. Engl. J. Med. 278, 233-239 (1968)... 

Recently, inherited metabolic diseases have been described in which a particular enantiomeric form of a metabolite is exclusively excreted [42]. Typical examples are D(-l-)-glyceric aciduria [43] and L-2-hydroxyglutaric aciduria [44], Using conventional GC-MS for urinary organic acid screening, increased amounts of these... 

Once the configuration of the glyceric acids was known (in relation to the glyceraldehydes), it was then possible to relate other compounds to either of these, and each time a new compound was related, others could be related to it. In this way, many thousands of compounds were related, indirectly, to d- or L-glyceraldehyde, and it was determined that 34, which has the d configuration, is the isomer that... 

Rashed, M.S. et al., Chiral liquid chromatography tandem mass spectrometry in the determination of the configurations of glyceric acid in urine of patients with D-glyceric and L-glyceric acidurias, Biomed. Chromatogr, 16, 191, 2002. 

Problem 5.15 d-(-i-(-Glyceraldehyde is oxidized to (-)-glyceric acid, HOCH,CH(OH)COOH. Give the d,l designation of the acid. ... 

D-Glyceric acid (or D-2,3-dihydroxypropanoic acid C3H604, MW = 125.10) is a hydroxy acid derived from the oxidation of Cl of glycerol or glyceraldehyde to a carboxyl group various phosphorylated derivatives of L-glycerate are important intermediates in glucose metabolism (Fig. 3.5.3). 

Vicinal diols are cleaved with high yields to carboxylic acids (Eq. 5, Table 9). Thereby cis- and trans-i, 2-cyclooctanediol react at about the same rate. In the cleavage of l,2 5,6-di-0-isopropylidene-D-mannitol (76) to 2,3-O-isopropylidene-R-glyceric acid (77) 98% of the optical purity is retained. 

Step 6 involves the oxidation of D-glyceraldehyde 3-phosphate, accompanied by phosphorylation of the intermediate carboxylic acid, to produce D-l,3-bisphosphoglycerate. The enzyme is glyceral-dehyde-3-phosphate dehydrogenase. 

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