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PubMed1984

In vivo studies on the metabolic derangement in a patient with D-glyceric acidaemia and hyperglycinaemia.

In a mentally retarded boy, who excreted elevated amounts of glycine, D-glyceric acid and acylglycines and whose cells exhibited diminished D-glycerate dehydrogenase and glycine cleavage activity, investigations have been undertaken aiming at characterizing the relationship between the different accumulations. This was done in vivo by trying in a specific manner to alter in turn the degree of accumulation of each of the three classes of compounds and then monitoring changes in the others. The results suggest, that the D-glyceric acid accumulation is directly caused by the genetic defect, since the D-glyceric acid excretion was not altered by changes in degree of accumulation of either glycine or acylglycines. Similarly alterations in acylglycine excretion caused alterations in glycine but not in D-glyceric acid excretion. Based on these findings a model for the pathogenesis behind the accumulations of acylglycines and glycine is proposed.

Amino Acid Metabolism, Inborn Errors↗
PubMed2002

D-glyceric aciduria in a six-month-old boy presenting with West syndrome and autistic behaviour.

D-Glyceric aciduria is a disease with a very heterogeneous group of symptoms, with D-glyceric acid excretion as the chief common characteristic. Findings described in previous patients include progressive neurological impairment, hypotonia, seizures, failure to thrive and metabolic acidosis. However, there are also asymptomatic patients with mild neurological impairment. A six-month-old boy was admitted to our clinic with the complaints of dullness to his environment, seizures and autistic behaviour. EEG revealed multifocal generalized epileptic activity in a hypsarrhythmia pattern. Organic acid analysis (GC-MS) in urine revealed increased glyceric acid excretion. Analysis of the optical form of glyceric acid by a polarimetric method supported the diagnosis of D-glyceric aciduria. MRI showed white matter lesions with cerebral atrophy, particularly in the frontotemporal regions, and reversible abnormalities in the mesencephalon, thalami and globus pallidium resolving after fructose restriction in the diet. To our knowledge, this is the first case report of a patient with D-glyceric aciduria who presented with West syndrome and autistic behaviour in whom serial MRI findings are also defined.

Autistic Disorder↗
PubMed1990

Polysaccharides from Peptostreptococcus anaerobius and structure of the species-specific antigen.

The cell-envelope antigens of Peptostreptococcus anaerobius were extracted from intact cells by autoclave or alkaline treatment. The purified species-specific antigen (G) was identified among several polysaccharides obtained from the extracts by successive treatments with ribonuclease and pronase followed by ion-exchange and gel-filtration chromatography. G was investigated by 13C- and 31P-n.m.r. spectroscopy, titrimetry, elemental analysis, and gas-liquid chromatography. Oxidation of G with NaIO4 followed by reduction with NaBH4 and mild acid hydrolysis yielded the Smith degradation product of G (GS). Treatment of G and GS with 48% HF gave the respective dephosphorylated products GF and GSF. The structures of GS, GF, and GSF were investigated by 13C-n.m.r. spectroscopy, methylation analysis, and gas-liquid chromatography-mass spectrometry. The principal constituents of G were 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), D-glyceric acid, and phosphate as a diester, in the ratio 2:1:1, and a minor amount of D-glucose (beta-D-Glcp). GS contained D-GlcNAc, D-glyceric acid, glycerol, and phosphate in a 1:1:1:1 ratio. GF and GSF contained D-GlcNAc and D-glyceric acid in the ratios 2:1 and 1:1, respectively. A structure for the principal repeating unit of polymeric G compatible with the analytical data consists of alpha-D-GlcpNAc-(1----3)-alpha-D-GlcpNAc-(1----2)-D-glyceric acid units linked through C-6'-C-6" phosphate diester bridges. This structure is novel for two reasons: (a) unsubstituted glyceric acid residues occur as aglycons in the repeating structure, and (b) phosphate diester bridges link nonanomeric glycose carbons in a non-nucleic acid polymer. The structural role of the minor amount of beta-D-Glcp in G remains unknown.

Antigens, Bacterial↗
PubMed1969

Metabolism of D- and L-glyceraldehyde in adipose tissue: a stereochemical probe for glycerokinase activity.

Distributions of (14)C have been determined in free glycerol, in glycerol from triglycerides, in glucose from glycogen, and in lactate after incubation of d-glyceraldehyde-3-(14)C and l-glyceraldehyde-3-(14)C with rat adipose tissue. The distributions are interpreted in terms of presently accepted possible reactions for the initial metabolism of glyceraldehyde. Formation of glycerol-1-(14)C from d-glyceraldehyde-3-(14)C indicates that in adipose tissue glyceraldehyde is reduced to glycerol. Incorporation of (14)C from d-glyceraldehyde-3-(14)C into carbon 3 of the glycerol of triglyceride indicates that d-glyceraldehyde is either phosphorylated or oxidized to d-glyceric acid, or both, in its initial metabolism. Incorporation of (14)C from l-glyceraldehyde-3-(14)C into carbon 3 of glycerol indicates that l-glyceraldehyde is reduced to glycerol, which is phosphorylated and (or) converted to d-glyceric acid via l-glyceric acid. Some (14)C from l-glyceraldehyde-3-(14)C is incorporated into carbon 1 of glycerol of triglycerides and carbon 4 of glycogen; the explanation for this incorporation is uncertain.

Adipose Tissue↗
PubMed1985

Structure of a novel phosphoglycolipid from Deinococcus radiodurans.

The chemical structure of a major phosphoglycolipid from Deinococcus radiodurans has been shown to be 2'-O-(1,2-diacyl-sn-glycero-3-phospho)-3'-O-(alpha-galactosyl)-N-D-gl yceroyl alkylamine. By infrared spectroscopy, the lipid was shown to contain both carbonyl ester and amide linkages. Chemical analysis demonstrated a molar ratio of fatty acid, carbohydrate, and phosphorus of 2:1:1. The lipid was shown to contain an sn-3-phosphatidic acid backbone by digestion with phospholipase A2. Phosphodiester bond cleavage of the lipid with hydrofluoric acid liberated a component which contained galactose, glyceric acid, and alkylamines. Using NMR and permethylation/hydrolysis procedures, galactose was shown to be linked alpha-glycosidically to the 3-O-position of glyceric acid.

Chemical Phenomena↗
PubMed1998

Highly potent bisphosphonate ligands for phosphoglycerate kinase.

We have synthesized a series of novel analogs of 1, 3-bisphospho-D-glyceric acid, 1,3-BPG,3 and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methanephosphonic acids replace the two phosphate monoesters of 1, 3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1, 3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for pKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

Diphosphoglyceric Acids↗
PubMed1987

Biosynthesis of the mycobacterial O-methylglucose lipopolysaccharide. Characterization of putative intermediates in the initiation, elongation, and termination reactions.

From the 70% ethanol extract of Mycobacterium smegmatis cells, we isolated a mixture of weakly acidic oligosaccharides composed mainly of glucose and 6-O-methylglucose. The elution pattern from a Bio-Gel P-4 column suggested that the oligosaccharides were smaller than the O-methylglucose polysaccharide (MGP) and could be biosynthetic precursors. Analysis by fast-atom-bombardment mass spectrometry revealed that the oligosaccharides fit into a pattern for polysaccharide synthesis based on an alternate glucosylation-methylation mechanism until the chain reached the composition methylglucose11glucose5glyceric acid, at which time 2 glucose units are added to give glucose2methylglucose11glucose5glyceric acid. The addition of the last 2 glucoses and methylation of one of them to give mature MGP (methylglucose1glucose3methylglucose11glucose5glyceric acid) apparently occurs rapidly because the expected intermediates were not observed. Only 4 glucose units are present at the glyceric acid end of some molecules during all stages of the elongation process, and these represent precursors of a minor MGP homolog with an extra methyl group on the beta 1----3-linked glucose unit of MGP. alpha-D-Glucopyranosyl-(1----2)-D-glyceric acid and alpha-D-glucopyranosyl-(1----6)-alpha-D-glucopyranosyl-(1----2)-D-glycer ic acid were also isolated from the extract and correspond in structure to the expected initial precursors.

Carbohydrate Sequence↗
PubMed1976

D-glyceric-acidaemia and non-ketotic hyperglycinaemia. Clinical and laboratory findings in a new syndrome.

The clinical and laboratory findings in a 2 1/2-year-old boy with non-ketotic hyperglycinaemia are reported. Except for a somewhat impaired liver function there was a picture similar to the cases previously reported in the literature. The patient deviated from the classical description, however, in the excretion of large amounts of D-glyceric acid in the urine. The same compound was also repeatedly found in the serum. It is suggested that the large amounts of glycine found in various body fluids are secondary to a hitherto undescribed enzymatic defect in the degradation of D-glyceric acid.

Amino Acid Metabolism, Inborn Errors↗
PubMed1975

The mechanism of end product inhibition of serine biosynthesis. V. Mechanism of serim inhibition of phosphoglycerate dehydrogenases.

The reduction of enzyme-bound DPN constitutes a half-reaction of phosphoglycerate dehydrogenase and has been investigated fluorometrically. Serine was found to inhibit the half-reaction to the same extent and with the same degree of cooperation as the steady state reaction. This finding identifies the ternary complex conversion as the point in the reaction sequence at which serine inhibition occurs. Delta H determinations for the half-reaction showed no difference whether serine was or was not present and led to the conclusion that the inhibitory effect of serine could only manifest itself through the delta S term in the expression for the formation of the activated transition state complex. DL-3-P[2-2H]glyceric acid showed no primary isotope effect in the half-reaction. This result excludes hydrogen transfer as the rate-limiting step in the half-reaction and confirms that an isomerization step, affected by serine, exists in the ternary complex conversion scheme. The deuterated 3-P-glyceric acid shows an isotope effect of 2 in the steady state reaction.

Alcohol Oxidoreductases↗
PubMed1977

Role of rat-liver alcohol dehydrogenase in the glycerol pathway to L-lactate in homogenates.

14C-Distribution in the C3-chain of L-lactate after incubation of various 14-C-labelled prescursors ([1-14C] and [3-14C] glycerol; [3-14C] glyceraldehyde and glycerid acid; D- and L-[3-14C] serine; [1-14C] fructose and [6-14C] glucose) with homogenate showed that (1) most of the glycerol is metabolized to L-lactate via D-glyceraldehyde; the remainder may possibly form L-lactate via dihydroxyacetone; (2) a part of D-glyceraldehyde and D-glyceric acid may produce glycerol before L-lactate is formed; (3) D and L-serine do not form measurable amounts of L-lactate via D-glyceric acid; (4) rat-liver alcohol dehydrogenase (E.N.1.1.1.1) does not contribute to conversion to L-lactate of dihydroxyacetone phosphate from fructose nor of D-glyceraldehyde phosphate from glucose.

Alcohol Oxidoreductases↗
PubMed1994

Structure and physical properties of the extracellular polysaccharide PS-P4 produced by Sphingomonas paucimobilis P4 (DSM 6418).

A new strain, Sphingomonas paucimobilis P4 (DSM 6418), was found during a screening programme for exopolysaccharide-producing bacteria. The highly viscous fermentation broth yields a polysaccharide (up to 10 kg/m3), named PS-P4, and shows thixotropic flow behaviour. In the presence of phosphate ions, PS-P4 forms aqueous gels after heating and cooling at alkaline pH. After isolation and purification of the exopolysaccharide, structural analysis by 1D and 2D 1H NMR spectroscopy and mass spectrometry was performed. The deacylated exopolysaccharide has the following repeating trisaccharide structure:-->4)-beta-D-Glcp-(1-->4)-alpha-L-Rhap-(1-->3)-beta-D- Glcp(1-->Additionally, the presence of ester-bound acetic acid, D-glyceric acid, and (R)-3-hydroxybutyric acid in the native polysaccharide was demonstrated.

Carbohydrate Sequence↗
PubMed1979

A compound representing the D-glycerate terminus of the methylglucose-containing polysaccharide of Mycobacterium smegmatis.

In order to study the structure of the methylglucose-containing polysaccharide (MGP) of Mycobacterium smegmatis by NMR spectroscopy, we have prepared the model compound O-alpha-D-glucopyranosyl-(1 leads to 2)-D-glyceric acid. This compound, which represents the aglycon-containing terminus of MGP, was made from leucorse [O-alpha-D-glucopyranosyl-(1 leads to 5)-D-fructopyranose] by successive treatment with sodium borohydride, lead tetraacetate, and hypobromite. The structure of O-alpha-D-glucopyranosy.-(1 leads to 2)-D-glyceric acid was confirmed by chemical and enzymic methods. 13C and 1H NMR spectra of this compound, together with spectra of several disaccharides, were obtained for future reference in the polysaccharide study. The nine resonances in the 13C spectrum were assigned by comparison with the spectrum of methyl alpha-D-glucopyranoside. Analysis of the 1H NMR spectrum showed that the two methylene protons on C-3 of the glycerate moiety were less equivalent in the sodium salt than in the acid. This may be attributable to hydrogen bonding between the carboxylate and the hydrogen atom of the glycerate 3-hydroxyl group.

Carbohydrate Conformation↗
PubMed1976

The synthesis of chiral glycerides starting from D- and L-serine.

A method for synthesizing chiral glycerides starting from L- or D-serine is described. Optically-active serine (both enantiomers are commerically available) was transformed into glyceric acid by stereospecific diazotization. The configuration at carbon atom 2 was maintained during the reaction. The glyceric acid was then converted into optically pure isopropylideneglycerol - which is an important intermediate in the synthesis of mono-, di- and triglyderides - by esterification followed by acetalization with acetone and reduction with lithium aluminium hydride. Reaction of this intermediate with triphenylphosphine in tetrachloromethane followed by acid-catalysed hydrolysis and dehydrohalogenation provided optically-active glycidol (2,3-epoxy-1-propanol). The epoxy ring of an ester of glycidol and a fatty acid was then opened stereospecifically with retention of configuration by heating the glycidol ester in the presence of a second fatty acid and a catalyst. This yielded a chiral 1,3-diglyceride which could be converted into a chiral triglyceride.

Diglycerides↗
PubMed1976

Starch degradation in isolated spinach chloroplasts.

A method for loading isolated intact spinach (Spinacia oleracea L.) chloroplasts with (14)C-starch is described. These intact chloroplasts were incubated aerobically in the dark for 30 minutes. Radioactivity in starch declined and glyceric acid 3-phosphate and maltose were the major radioactive products. It is proposed that starch is degraded within the chloroplast to glyceric acid 3-phosphate and to maltose.

Journal Article↗
PubMed1975

32P distribution into 2,3-bisphosphoglyceric acid from human erythrocytes following molybdate-catalyzed hydrolysis.

Normal human washed erythrocytes were incubated in autologous plasma with 32P for varying periods of time. 2,3-Bisphosphoglyceric acid the major organic phosphate ester of red cells, was first isolated and purified by anion-exchange chromatography; subsequently, the C-2Pi was selectively hydrolyzed by a molybdate-catalyzed reaction. The C-2-bound Pi of 2,3-P2-glyceric acid was found to have a significantly higher specific activity than C-3 Pi. Intramolecular equilibration was not reached until the 180-min incubation. No evidence of overhydrolysis or internal randomization by the molybdate reaction was noted which was confirmed following hydrolysis of double-label 2,3-P2-glyceric acid 32P C-2, 33P C-3.

Chromatography↗
PubMed2006

Conformational analyses of 2,3-dihydroxypropanoic acid as a function of solvent and ionization state as determined by NMR spectroscopy.

Vicinal (1)H--(1)H coupling constants were used to determine the conformational preferences of 2,3-dihydroxypropanoic acid (1) (DL-glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J(12) and J(13) were confirmed through the point-group substitution of the C-3 hydrogen with deuterium, yielding rac-(2SR,3RS)-[3-(2)H]-1, and the observation of only J(13) in the (1)H NMR spectra. While hydrogen bonding and steric strain may be expected to drive the conformational equilibrium, their role is overshadowed by a profound gauche effect between the vicinal hydroxyl groups that mimics other substituted ethanes, such as 1,2-ethanediol and 1,2-difluoroethane. At low pH, the conformational equilibrium is heavily weighted toward the gauche-hydroxyl rotamers with a range of 81% in DMSO-d(6) to 92% in tert-butyl alcohol-d(10). At high pH, the equilibrium exhibits a larger dependence upon the polarity and solvating capability of the medium, although the gauche effect still dominates in D(2)O, 1,4-dioxane-d(8), methanol-d(4), and ethanol-d(6) (96, 89, 85, and 83% gauche-hydroxyls respectively). The observed preference for the gauche-hydroxyl rotamers is believed to stem primarily from hyperconjugative sigma(C--H) --> sigma*(C--OH) interactions.

Journal Article↗
PubMed1992

Comparison of post-mortem urinary and vitreous humour organic acids.

We have analysed organic acid profiles in 74 samples of post-mortem vitreous humour from the sudden infant death syndrome and compared the profiles to those obtained from the corresponding urine or bladder wall swab. There was a high degree of correlation indicating that vitreous humour analysis in high-risk infants is an appropriate analytical strategy when urine is not available. In our patient sample two infants had evidence of abnormal methylmalonic acid metabolism, one had glyceric aciduria (and elevated levels of vitreous humour glyceric acid), one had evidence of pre-existing liver damage as judged by the presence of 4-hydroxyphenyllactic acid, one had a non-ketotic dicarboxylic aciduria indicating inhibited fatty acid oxidation and two patients had significant long-chain 3-hydroxydicarboxylic acids and evidence of paracetamol ingestion.

Carboxylic Acids↗
PubMed1977

Properties of Escherichia coli mutants deficient in enzymes of glycolysis.

Physiological properties of mutants of Escherichia coli defective in glyceraldehyde 3-phosphate dehydrogenase, glycerate 3-phosphate kinase, or enolase are described. Introduction of a lesion in any one of the reversible steps catalyzed by these enzymes impaired both the glycolytic and gluconeogenic capabilities of the cell and generated an obligatory requirement for a source of carbon above the block (gluconeogenic) and one below (oxidative). A mixture of glycerol and succinate supported the growth of these mutants. Mutants lacking glyceraldehyde 3-phosphate dehydrogenase and glycerate 3-phosphate kinase could grow also on glycerol and glyceric acid, and enolase mutants could grow on glycerate and succinate, whereas double mutants lacking the kinase and enolase required l-serine in addition to glycerol and succinate. Titration of cell yield with limiting amounts of glycerol with Casamino Acids in excess, or vice versa, showed the gluconeogenic requirement of a growing culture of E. coli to be one-twentieth of its total catabolic and anabolic needs. Sugars and their derivatives inhibited growth of these mutants on otherwise permissive media. The mutants accumulated glycolytic intermediates above the blocked enzyme on addition of glucose or glycerol to resting cultures. Glucose inhibited growth and induced lysis. These effects could be substantially overcome by increasing the osmotic strength of the growth medium and, in addition, including 5 mM cyclic adenosine 3',5'-monophosphate therein. This substance countered to a large extent the severe repression of beta-galactosidase synthesis that glucose caused in these mutants.

Carbohydrate Metabolism↗