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At least 19 recordsLinked to original sources
PubMed2002

Chiral liquid chromatography tandem mass spectrometry in the determination of the configuration of glyceric acid in urine of patients with D-glyceric and L-glyceric acidurias.

Glyceric acid is a highly polar chiral carboxylic acid that is usually not detected during routine organic acid analysis. Increased excretion is observed in two phenotypically distinct and rare inherited metabolic diseases, D-glyceric aciduria, and L-glyceric aciduria (also known as primary hyperoxaluria type 2). The determination of the exact configuration of the excreted glyceric acid is necessary for the accurate diagnosis of D-glyceric aciduria and for the differentiation between type 1 and type 2 primary hyperoxaluria. The separation of the two stereoisomers was achieved using a narrow-bore ristocetin A glycopeptide antibiotic silica gel bonded column. Triethylamine acetate at pH 4.1 with 10% methanol was used as mobile phase. The column was directly interfaced to a triple quadrupole tandem mass spectrometer and the electrospray ion source was operated in the negative ion mode. Three parent-to-daughter transitions were employed to specifically detect eluting glyceric enantiomers from essentially untreated urine samples. The two forms of glyceric acid were satisfactorily separated at 3.6 and 4.5 min. Application of the method led to the confirmation of three cases of D-glyceric aciduria from three different families. Two other cases are suspected to be L-glyceric aciduria but further confirmation is needed. The method allowed the detection of the glyceric acid stereoisomers in control urine where it was found without exception that L-glyceric was the predominate metabolite.

Chromatography, Liquid↗
PubMed1996

Phosphorylation of glyceric acid in aqueous solution using trimetaphosphate.

The phosphorylation of glyceric acid is an interesting prebiotic reaction because it converts a simple, potentially prebiotic organic molecule into phosphate derivatives that are central to carbohydrate metabolism. We find that 0.05 M glyceric acid in the presence of 0.5 M trimetaphosphate in alkaline solution gives a mixture of 2- and 3-phosphoglyceric acids in combined yields of up to 40%.

Deuterium Oxide↗
PubMed2005

Differential chemical diagnosis of primary hyperoxaluria type II. Highly sensitive analysis of optical isomers of glyceric acid by GC/MS as diastereoisomeric derivatives.

We established a separation method for the optical isomers of glyceric acid in urine by modifying the derivatization steps of the procedure used for the screening and diagnosis. The trimethylsilyl derivatization step in the mass screening procedure was replaced by O-acetyl-(+)-2-butylation, and the samples were analyzed under equivalent GC/MS conditions by capillary gas chromatography on a DB-5MS column. This method can be applied to cases that show a high urinary concentration of glyceric acid to obtain a differential diagnosis of primary hyperoxaluria type II and d-glyceric aciduria easily. l-Glyceric acid was also isolated from the urine of healthy controls as one of the main peaks.

Diagnosis, Differential↗
PubMed1976

[Characterisation of D(-)glyceric acid from Nocardia caviae (author's transl)].

A glycolipid was found in a strain of Nocardia caviae. It consists of glucose, myristic, palmitic and stearic acids and a polyhydroxylated acid. The structure of this hydroxyacid was demonstrated by the identification of the product glycerol after LiA1H4 reduction of the glycolipid methyl ester and subsequent hydrolysis, by comparison of the infrared spectra of the hydroxyacid and glyceric acid, by gas chromatography of acetylated methyl and ethyl esters of the polyhydroxylated acid and of standard glyceric acid and by mass spectrometry of the diacetylated methyl ester. The hydroxyacid from the glycolipid is D(-)glyceric acid, a compound rarely found amongst natural products.

Glucose↗
PubMed1977

Determination of the configurations of lactic and glyceric acids from human serum and urine by capillary gas-liquid chromatography.

The separation of the enantiomers of lactic and glyceric acids can be achieved by capillary gas chromatography on SP-1000 using the corresponding O-acetylated methyl esters. The structures of the derivatives were proved by proton magnetic resonance spectroscopy and mass spectrometry. The method has been used for the determination of the absolute configuration of lactic and glyceric acids isolated from serum and urine from different patients.

Capillary Action↗
PubMed1981

Structure of 2',3'-di-O-acyl-alpha-D-glucopyranosyl-(1 leads to 2)-D-glyceric acid, a new glycolipid from Nocardia caviae.

The structure of a new glycolipid isolated from the acetone-soluble lipids of the strain of Nocardia caviae has been determined. The water-soluble moiety contains one mole of D-glucose and one mole of D(-)-glyceric acid; the lipid moiety is a mixture of myristic, palmitic and stearic acids with small amounts of oleic acid. The structure of the deacylated compound was determined by periodate oxidation, methylation and enzymatic degradation. The localization of fatty acid residues at 2',3' on glucose was established by methylation and mass spectrometry. The structure was confirmed by 13C NMR spectrometry of the glycolipid and of the deacylated compound. This glycolipid is a 2'.3'-di-O-acyl-alpha-D-glucopyranosyl-(1 leads to 2)-D-(-)-glyceric acid.

Chemical Phenomena↗
PubMed1984

Stereochemical determination of carbon partitioning between photosynthesis and photorespiration in C3 plants: use of (3R)-D-[3-3H1, 3-14C]glyceric acid.

When (3R)-D-[3-3H1,3-14C]glyceric acid is supplied in tracer amounts to illuminated tobacco leaf discs, the acid penetrates to the chloroplasts without loss of 3H, and is phosphorylated there. Subsequent metabolism associated with the reductive photosynthetic cycle fully conserves 3H. Oxidation of ribulose bisphosphate (RuBP) by RuBP carboxylase-oxygenase (EC 4.1.1.39) results in the formation of (2R)-[2-3H1, 14C]glycolic acid which, on oxidation by glycolate oxidase (EC 1.1.3.1), releases 3H to water. Loss of 3H from the combined photosynthetic and photorespiratory systems is, therefore, associated with the oxidative photorespiratory loop. Assuming steady-state conditions and a basic metabolic model, the fraction of RuBP oxidized and the photorespiratory carbon flux relative to gross or net CO2 fixation can be calculated from the fraction of supplied 3H retained in the triose phosphates exported from the chloroplasts. This retention can be determined from the 3H:14C ratio for glucose obtained from isolated sucrose. The dependence of 3H retention upon O2 and CO2 concentrations can be deduced by assuming simple competitive kinetics for RuBP carboxylase-oxygenase. The experimental results confirmed the stereochemical assumptions made. Under conditions of negligible photorespiration 3H retention was essentially complete. The change in 3H retention with O2 and CO2 concentrations were investigated. For leaf discs (upper surface up) in normal air, it was estimated that 39% of the RuBP was oxidized, 32% of the fixed CO2 was photorespired, and the photorespiration rate was 46% of the net photosynthetic CO2 fixation rate. These are minimal estimates, as it is assumed that the only source of photorespired CO2 is glycine decarboxylation.

Carbon↗
PubMed1992

High-performance liquid chromatographic assay for L-glyceric acid in body fluids. Application in primary hyperoxaluria type 2.

We describe a liquid chromatographic technique to determine L-glycerate in body fluids. The method is based on the derivatisation of the L-glycerate by incubation with lactate dehydrogenase and nicotinamide-adenine dinucleotide in the presence of phenylhydrazine. Oxidation of L-glycerate forms beta-hydroxypyruvate which is converted in turn into the related phenylhydrazone. The UV-absorbing derivative is determined using reversed-phase high performance liquid chromatography. The sensitivity was 5 mumol/l and 50 microliters of sample were required. The imprecision relative standard deviation was 4.5% and the recovery was 96.5 +/- 6.8% for L-glycerate in plasma. L-Glycerate concentrations in urine and plasma were less than 5 mumol/l in both normal individuals and patients with glycolic aciduria. In a patient with systemic oxalosis and normal plasma glycolate, plasma L-glyceric acid was 887 mumol/l.

Body Fluids↗