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PubMed1998

Infants in Trinidad excrete more 5-L-oxoproline (L-pyroglutamic acid) in urine than infants in England: an environmental not ethnic difference.

The demand for glycine to satisfy normal growth during early life is considerable and most has to be made endogenously. The extent to which adequate glycine is available can be assessed by measuring the urinary excretion of 5-L-oxoproline. The excretion of 5-L-oxoproline at 6 weeks of age for infants in Trinidad of African, Indian or mixed parentage (398 mumol/mmol creatinine) was significantly greater than for infants born in England of Caucasian parentage (194 mumol/mmol creatinine). There was no relationship between 5-L-oxoproline excretion and either sex or pattern of feeding. There were significant inverse relationships between 5-L-oxoproline/creatinine and birth weight, and head circumference either at birth or 6 weeks of age, suggesting that limited availability of glycine is associated with poorer growth before and after birth. For a group of infants born in England of Indian parentage, excretion of 5-L-oxoproline (155 mumol/mmol creatinine) was not different to infants of Caucasian parentage, but significantly less than infants born in Trinidad. The demonstration that 5-L-oxoproline/creatinine was similar in infants born in England, regardless of parentage, shows that the differences between England and Trinidad are related to environment and are unlikely to be accounted for by genetic differences or ethnicity.

Africa↗
PubMed2001

Electrophilic fluorination of pyroglutamic acid derivatives: application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids.

Electrophilic fluorination of enantiomerically pure 2-pyrrolidinones (4) derived from (L)-glutamic acid has been investigated as a method for the synthesis of single stereoisomers of 4-fluorinated glutamic acids. Reaction of the lactam enolate derived from 9 with NFSi results in a completely diastereoselective monofluorination reaction to yield the monocyclic trans-substituted alpha-fluoro lactam product 21. Unfortunately, a decreased kinetic acidity in 21 and other structurally related monofluorinated products renders them resistant to a second fluorination. In contrast, the bicyclic lactam 12 is readily difluorinated under the standard conditions described to yield the alpha,alpha-difluoro lactam 24. The difference in reactivity between the two types of related lactams is attributed mainly to the presence or lack of a steric interaction between the base used for deprotonation and the protecting group present in the pyrrolidinone substrates. This conclusion was reached based on analysis of the X-ray crystal structure of 21, molecular modeling, and experimental evidence. The key intermediates 21 and 24 are converted to (2S,4R)-4-fluoroglutamic acid and (2S)-4,4-difluoroglutamic acid, respectively.

Chromatography, Thin Layer↗
PubMed1997

Urinary 5-L-oxoproline (pyroglutamic acid) excretion is greater in infants in Jamaica than in infants in England.

OBJECTIVE: To determine the pattern of excretion in urine of 5-L-oxoproline, as a measure of glycine status, during the first six weeks of life in Jamaican infants. DESIGN: Spot samples of urine were collected from term and preterm infants at birth and longitudinally to four weeks of age, or at six weeks of age. 5-L-oxoproline was isolated by column chromatography and hydrolysed to L-glutamic acid, which was measured enzymatically and the results expressed relative to creatinine excretion. SETTING: Maternity wards and postnatal clinic of the University Hospital of the West Indies. SUBJECTS: African-Caribbean infants, 19 term and 21 preterm, from birth to four weeks of age, and 79 term infants at six weeks of age. RESULTS: There were no differences between term and preterm infants. Excretion of 5-L-oxoproline increased progressively from birth, 141 mumol/mmol creatinine, to 270 mumol/mmol creatinine at four weeks of age. At six weeks of age, excretion was significantly greater than at birth or four weeks of age, 525 mumol/mmol creatinine. Compared with infants born in England, the excretion of 5-L-oxoproline was not different at birth, but was significantly greater in Jamaican infants at six weeks of age. CONCLUSIONS: Glycine status, indicated by increased excretion of 5-L-oxoproline, is marginal in Jamaican infants at six weeks of age, and this possibly reflects a limitation in the endogenous biosynthesis of glycine due to a dietary limitation of folate or vitamin B-12.

Chromatography↗
PubMed2002

Rapid determination of underivatized pyroglutamic acid, glutamic acid, glutamine and other relevant amino acids in fermentation media by LC-MS-MS.

Determination of amino acids in a complex matrix without derivatization is advantageous, however, difficulties are found in both the detection and the separation of those compounds. In this study, a rapid and reliable LC-MS-MS method for the quantitation of underivatized amino acids in exocellular media was established. Injections were made directly after centrifugation of the samples, without further preparation. The separation of seven underivatized amino acids was achieved on a reversed-phase C18 column with pentadecafluorooctanoic acid as a volatile ion-pair reagent, and the specific detection of most amino acids was achieved by MS-MS of the specific transitions [M + H]+-->[M + H - 46]+. The calibration curves of all analytes were linear over the range of 1.0-1000 microg ml(-1) and the detection limits ranged from 0.1 to 5 ng ml(-1), with an injection volume of 20 microl. The inter-day and intra-day precisions ranged from 2.6 to 5.7% and 4.8 to 8.2%, respectively; the mean recoveries of the seven analytes were 81-104%, 91-107% and 93-101% respectively at the spiked level of 10, 40 and 200 microg ml(-1). A large number of fermentation samples were analysed using this method. The technique is simple, rapid, selective and sensitive, and shows potential for the high-throughput quantitation of amino acids from other biological matrices.

Amino Acids↗
PubMed2003

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues.

Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

Alkylation↗
PubMed2005

Recurrent high anion gap metabolic acidosis secondary to 5-oxoproline (pyroglutamic acid).

High anion gap metabolic acidosis in adults is a severe metabolic disorder for which the primary organic acid usually is apparent by clinical history and standard laboratory testing. We report a case of recurrent high anion gap metabolic acidosis in a 48-year-old man who initially presented with anorexia and malaise. Physical examination was unrevealing. Arterial pH was 6.98, P co 2 was 5 mm Hg, and chemistry tests showed a bicarbonate level of 3 mEq/L (3 mmol/L), anion gap of 32 mEq/L (32 mmol/L), and a negative toxicology screen result, except for an acetaminophen (paracetamol) level of 7.5 mug/mL. Metabolic acidosis resolved with administration of intravenous fluids. Subsequently, he experienced 5 more episodes of high anion gap metabolic acidosis during an 8-month span. Methanol, ethylene glycol, acetone, ethanol, d -lactate, and hippuric acid screens were negative. Lactate levels were modestly elevated, and acetaminophen levels were elevated for 5 of 6 admissions. These episodes defied explanation until 3 urinary organic acid screens, obtained on separate admissions, showed striking elevations of 5-oxoproline levels. Inborn errors of metabolism in the gamma-glutamyl cycle causing recurrent 5-oxoprolinuria and high anion gap metabolic acidosis are rare, but well described in children. Recently, there have been several reports of apparent acquired 5-oxoprolinuria and high anion gap metabolic acidosis in adults in association with acetaminophen use. Acetaminophen may, in susceptible individuals, disrupt regulation of the gamma-glutamyl cycle and result in excessive 5-oxoproline production. Suspicion for 5-oxoproline-associated high anion gap metabolic acidosis should be entertained when the cause of high anion gap metabolic acidosis remains poorly defined, the anion gap cannot be explained reasonably by measured organic acids, and there is concomitant acetaminophen use.

Acetaminophen↗
PubMed1996

Urinary excretion of 5-L-oxoproline (pyroglutamic acid) is increased in normal adults consuming vegetarian or low protein diets.

A method for measuring 5-L-oxoproline in urine, which involves isolation by short-column chromatography, acid hydrolysis to glutamic acid and enzymic assay of glutamic acid, was used to measure the rate of excretion in normal adults, aged 20 to 45 y. There was no difference in the daily excretion between omnivorous males (217 micromol/d) and females (195 micromol/d). In vegetarian males, urinary 5-L-oxoproline (404 micromol/d) was significantly greater than in vegetarian females (267 micromol/d, P = 0.013). Compared with omnivorous males or females, excretion of 5-L-oxoproline was significantly greater in vegetarian males (P < 0.0001) and females (P= 0.005). When normal adults consumed a diet in which the protein content was controlled at either 4.0 or 6.2 g N/d for 5 d, there was a significant increase in urinary 5-L-oxoproline on d 5, compared with either d 1 or 4. There was a significant inverse linear relationship between the increased urinary 5-L-oxoproline on the fifth dietary day and the nitrogen content of the diet. On the basis of this relationship, when the urinary excretion of 5-L-oxoproline (320 micromol/d) for vegetarians was predicted from an estimate of their dietary intake of nitrogen, the estimate was, on average, close to the measured value (345 micromol/d). As a matter of course, vegetarians excrete more 5-L-oxoproline in urine than do omnivores, and we speculated that this difference might be accounted for by differences in dietary nitrogen and the endogenous capacity for de novo synthesis of glycine.

Adult↗
PubMed1996

Urinary excretion of 5-L-oxoproline (pyroglutamic acid) is increased during recovery from severe childhood malnutrition and responds to supplemental glycine.

We hypothesized that a limitation in the endogenous formation of glycine might constrain catch-up growth during recovery from severe childhood malnutrition. The urinary excretion of 5-L-oxoproline is increased when the glycine available for glutathione synthesis is limited. Urinary excretion of 5-L-oxoproline was measured throughout recovery in 12 children (aged 16 +/- 6 mo) with severe malnutrition. Urinary 5-L-oxoproline was similar at admission and after recovery, but was increased significantly during rapid catch-up growth. There was a significant relationship between the rate of weight gain and 5-L-oxoproline excretion in urine. In nine children (aged 15 +/- 5 mo), the effect of oral supplementation with glycine, [1.7 mmol/(kg x d) for 48 h] during rapid catch-up growth on 5-L-oxoprolinuria and blood glutathione concentration was determined. In seven of the nine children weight gain was less than 17 g/(kg x d) and following oral glycine supplements 5-L-oxoproline excretion was reduced up to 64% and blood glutathione concentration increased up to 100%. In the two children who were gaining weight at a rate > 17 g/(kg x d), glycine supplementation was associated with a further increase in 5-L-oxoproline excretion and a decrease in blood glutathione. If 5-L-oxoproline is an index of the relative availability of glycine, then the data indicate that glycine may be limiting during rapid catch-up growth. This would have important implications for repletion of muscle and gain in height.

Aging↗
PubMed1997

Urinary excretion of 5-L-oxoproline (pyroglutamic acid) during early life in term and preterm infants.

Urinary 5-L-oxoproline was measured in term and preterm infants from shortly after birth until 6 weeks of postnatal age to determine their ability to synthesise glycine. In term infants the excretion was five to 10 times that seen in normal adults, increasing from 105 mumol/mmol creatinine in the first 72 hours after birth to 170 mumol/mmol creatinine at 6 weeks of age. There was a significant inverse linear correlation between the excretion of 5-L-oxoproline and length of gestation or birthweight. By 6 weeks of age there was no longer a significant difference in 5-L-oxoproline between term and preterm infants. There was no difference in the excretion of 5-L-oxoproline between boys and girls, or between infants fed on human milk or an artificial formula. If, in part, variability in the excretion of 5-L-oxoproline is determined by the extent to which the endogenous formation of glycine is adequate, then glycine formation may be marginal during early life, more so in preterm than in term infants, providing additional evidence that glycine is a conditionally essential amino acid in the neonate.

Birth Weight↗