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PubMed1997

Asymmetric Electroreduction of Ketone and Aldehyde Derivatives to the Corresponding Alcohols Using Alcohol Dehydrogenase as an Electrocatalyst.

Asymmetric electroreduction of ketone and aldehyde derivatives was examined for two electrochemical reduction systems using alcohol dehydrogenase (ADH) as an electrocatalyst. The reaction system A is concerned with reduction of substrates catalyzed by ADH coupled with regeneration of cofactors by another enzyme with assistance of methyl viologen as an electron mediator, and the reaction system B is concerned with the use of ADH as the sole enzyme which catalyzes both reduction of substrates and regeneration of cofactors. In the latter case, a redox couple of phenethyl alcohol/acetophenone is used as an electron mediator to induce the reaction. The electrolysis using the system A allowed asymmetric reduction of acetophenone, propiophenone, phenoxy-2-propanone, pyruvic acid, and 2-phenylpropionaldehyde to the corresponding optically active alcohols with the enantiomer excesses (ee) close to 100% and the current efficiencies larger than 92%, and the turnover number of the cofactor higher than 50 was obtained for electrochemical reduction of phenoxy-2-propanone for 30 h. The reaction system B gave 100% ee for reduction of propiophenone, phenoxy-2-propanone, and pyruvic acid. However, the amount of products obtained was very small for reduction of benzoylformic acid, and a low enantiomer excess was obtained for reduction of phenylpropionaldehyde. Discussion is made focusing on what substrates are suitable for asymmetric reduction induced by the reaction system B.

Journal Article↗
PubMedDate not supplied

[Mechanism of the change in electrolyte and carbohydrate metabolism in the submandibular salivary gland in experimental botulism in rats].

Content of lactic and pyruvic acids, glycogen, sodium and potassium ions are well as the total LDH activity and its isoenzyme spectrum were not distinctly altered, when secretion of salivary glands was inhibited by administration of botulinic toxin into rats (within 48 hrs after the toxin treatment). But within 14 days the following alterations were observed in the impaired salivary glands: decrease in content of glycogen and potassium, increase in concentration of lactic and pyruvic acids, elevation in total LDH activity and change in its isoenzyme spectrum (increase in content of the fractions responsible for regulation of anaerobic metabolism).

Animals↗
PubMed1984

Study on the contraction and oxygen consumption induced by high K, Na-deficient solution in the urinary bladder and gall bladder of guinea-pig.

In urinary bladder and gall bladder of guinea-pig, the application of hyperosmotic 65.4 mM K solution induced a tonic contraction and increased the rate of oxygen consumption two or three times. The increased O2 consumption maintained steady level during 120 min. In isosmotic 154 mM K, Na-deficient solution, the tonic contraction gradually decreased and oxygen consumption also showed a transient increase followed by a small one. In the urinary bladder, the addition of pyruvic acid completely prevented the decline of the tonic contraction by iso-154K solution at 120 min, but this addition partially prevented it in the gall bladder. Hyperosmotic application of sucrose partially prevented it in the urinary bladder, but completely recovered it in the gall bladder. When NaCl was applied to iso-154K solution, the decrease of tonic contraction was prevented by half in both the muscles. The application of pyruvic acid and NaCl prevented the reduction of oxygen consumption by iso-154K solution in the urinary bladder, but in the gall bladder, this had little effect. There was a close correlation (r = 0.950) between the muscle tension and the rate of oxygen consumption in the urinary bladder at 120 min under various conditions. In the gall bladder, a correlation (r = 0.875) was also found between both when the results by hyperosmotic addition of NaCl and sucrose were omitted. In the urinary bladder, tension cost, a ratio of O2 consumption rate (mumol O2/g/min) to developed tension (kg force/cm2), was large (0.206) and similar to that of taenia coli; and that of gall bladder was small (0.130) and almost similar to that of vascular smooth muscle.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2002

Evidence for production of the phytohormone indole-3-acetic acid by cyanobacteria.

The ability of cyanobacteria to produce the phytohormone indole-3-acetic acid (IAA) was demonstrated. A colorimetric (Salkowski) screening of 34 free-living and symbiotically competent cyanobacteria, that represent all morphotypes from the unicellular to the highly differentiated, showed that auxin-like compounds were released by about 38% of the free-living as compared to 83% of the symbiotic isolates. The endogenous accumulation and release of IAA were confirmed immunologically (ELISA) using an anti-IAA antibody on 10 of the Salkowski-positive strains, and the chemical authenticity of IAA was further verified by chemical characterization using gas chromatography-mass spectrometry in Nostoc PCC 9229 (isolated from the angiosperm Gunnera) and in Nostoc 268 (free-living). Addition of the putative IAA precursor tryptophan enhanced IAA accumulation in cell extracts and supernatants. As the genome of the symbiotically competent Nostoc PCC 73102 contains homologues of key enzymes of the indole-3-pyruvic acid pathway, a transaminase and indolepyruvate decarboxylase (IpdC), the putative ipdC gene from this cyanobacterium was cloned and used in Southern blot analysis. Out of 11 cyanobacterial strains responding positively in the Salkowski/ELISA test, ipdC homologues were found in 4. A constitutive and possibly tryptophan-dependent production of IAA via the indole-3-pyruvic acid pathway is therefore suggested. The possible role of IAA in cyanobacteria in general and in their interactions with plants is discussed.

Amino Acid Sequence↗
PubMed1995

Overexpression and characterization of human tetrameric pyruvate dehydrogenase and its individual subunits.

Pyruvate dehydrogenase (E1), an alpha 2 beta 2 tetramer, is the first component of the pyruvate dehydrogenase complex which catalyzes a two-step oxidative decarboxylation of pyruvic acid. To overexpress human E1 and its subunits individually, cDNAs for the mature forms of human E1 alpha and E1 beta were subcloned either individually or together into a plasmid pQE-9 and expressed in Escherichia coli M15. A polyhistidine extension was added at the NH2-termini of the recombinant E1 alpha and E1 beta for the rapid purification of the proteins by Ni-nitrilotriacetic-agarose chromatography. The polyhistidine extension on either E1 alpha or E1 beta subunit did not affect the activity of the recombinant tetrameric E1. Highly purified recombinant human E1 catalyzed the partial reactions of the oxidative and nonoxidative conversion of pyruvic acid with the same efficiency as E1 purified from bovine kidney. Recombinant human E1 interacted with thiamin pyrophosphate by forming a charge transfer complex band at 330 nm that changed during the catalytic cycle. Recombinant human E1 was phosphorylated by E1-kinase (with concomitant inactivation) by incorporating nearly three phosphoryl groups per mole of E1. When expressed individually, E1 alpha and E1 beta subunits lacked any catalytic activity in the oxidative or nonoxidative reactions. Spectral studies demonstrated that there was no thiamin pyrophosphate binding to either recombinant E1 alpha or E1 beta subunit. The E1 alpha subunit retained the ability to be phosphorylated; however, the incorporation of phosphoryl groups into recombinant E1 alpha alone was only about 12% of that observed with the tetrameric E1. These findings show that both subunits are required for formation of the active center and catalysis.

Base Sequence↗
PubMedDate not supplied

[Formation of pyruvic and lactic acids in muscles diluted homogenate differing from the generally accepted glycolysis scheme].

When studying formation of pyruvic and lactic acids from fructose diphosphate the effect of dilution is found in the process of muscles homogenate incubation. Pyruvic acid accumulates only in samples with magnesium chloride added. The increase of lactic acid remains constant irrespectively of availability of conditions for pyruvate formation. Phosphoglycerate and phosphoenolpyruvate form pyruvic acid only in samples with magnesium chloride added without forming lactic acid. It is shown that in the muscles diluted homogenate (25 mg per 6 ml of mixture) lactic acid is formed under conditions unsuitable for pyruvic acid formation. Lactic acid is formed omitting the stages of 2-phosphoglycerate, phosphoenolpyruvate and pyruvate i.e. in the pathway different from a classical scheme of glycolysis.

Animals↗
PubMed1994

Intracellular pH responses of hybridoma and yeast to substrate addition and acid challenge.

The pHi responses of hybridoma and yeast cells to substrate and external acid additions were measured using the fluorescent pHi indicator, 9-aminoacridine. The pHi change, following CCCP addition, indicated by 9AA, compared very well with that indicated by BCECF. No change in pHi was observed following glucose or glutamine additions to hybridoma cells under glucose- and glutamine-absent conditions. Also, no change in pHi was observed when glucose was added in the presence of low glutamine and when glutamine was added in the presence of low glucose. However, in the presence of amiloride, the pHi of hybridoma cells decreased following glucose addition. Intracellular pH responses of hybridoma and yeast cells to decreases in external pH, effected by acid addition, were dependent on the cellular energy state and acid type. Cells controlled their pHi more tightly under energy-poor conditions compared to energy-rich conditions, and sulfuric acid (strong acid) caused larger changes in pHi compared to pyruvic acid (weak acid). In response to acid addition under energy-rich conditions, the magnitudes of pHi increases in hybridoma were smaller in the presence of amiloride compared to that in the absence of amiloride. Further, pHi responses to a decrease in external pH were slower at submetabolic temperatures.

Acids↗
PubMed2000

S-alk(en)yl-L-cysteine sulfoxides, alliinase and aroma in Leucocoryne.

Levels of S-alk(en)yl-L-cysteine sulfoxides, alliinase and enzymatically generated pyruvic acid were determined in the bulb, leaf and scape of five species and a natural hybrid of Leucocoryne (Liliaceae), a genus of ornamental geophytes indigenous to Chile. (+)-S-Methyl-L-cysteine sulfoxide (MCSO) was present in all plant parts of all species at levels between 0.09 and 1.41 mg g(-1) fr. wt. Trans-(+)-S-(1-propenyl)-L-cysteine sulfoxide (PRENCSO) was present in plant parts of three species only (L. angustipetala, L. oadorata and L. purpurea) at levels between 0.12 and 1.82 mg g(-1) fr. wt. No other S-alk(en)yl-L-cysteine sulfoxides were detected. Alliinase (EC 4.4.1.4) was detected in the leaf, bulb and scape of L. angustipetala and L. purpurea, only in the leaves of L. coquimbensis and L. purpurea x L. coquimbensis, and only in the bulb of L. odorata. Enzymatically generated pyruvic acid was detected in all plant parts of all species at levels between trace amounts and 5.33 micromol g(-1) fr. wt. As PRENCSO is produced only in Leucocoryne species exhibiting a strong and unpleasant onion-like aroma, it is probable that the enzymatic degradation of PRENCSO is the main cause of that aroma. Consequently, Leucocoryne cultivars should be selected in species and hybrids that lack the ability to synthesise PRENCSO.

Carbon-Sulfur Lyases↗
PubMed1998

Vanadium toxicology--an assessment of general health, haematological aspects and energy response in an Indian catfish Clarias batrachus (Linn).

The pervasive occurrence of vanadium in nature and its use in various industrial processes has increased its inputs in the environment. This has prompted us to elucidate the impact of vanadium on aquatic environment, the primary body for industrial effluent discharge. The energy response of the fish, Clarias batrachus, its haematological status including haemoglobin (Hb), haematocrit (Ht), leutocrit (Lt), mean corpuscular haemoglobin (MCH), mean corpuscular volume (MCV), mean corpuscular haemoglobin concentration (MCHC) etc. And overall general health conditions have been observed to be significantly hampered leading to deleterious alterations in the general metabolism of the fish following long term exposure to vanadate. The increase in muscle and tissue lactic acid (2-12 fold) in association with decrease in pyruvic acid (72% in muscle; 26% in liver) reflect a shift towards an anaerobic metabolism of the fish. We conclude that vanadium could be toxic for the fish in question under long term exposure at the doses under observation (2-10 mg L-1).

Anaerobiosis↗
PubMed1989

Pharmacokinetics and biotransformation of hydralazine acetone hydrazone, a metabolite of hydralazine, in the rat.

The pharmacokinetics of hydralazine acetone hydrazone (HAH), which is a metabolite of hydralazine (HP), was investigated after iv administration to rats. Plasma concentrations of HAH, HP, and hydralazine pyruvic acid hydrazone (HPH) were simultaneously determined by a specific HPLC method. A five-compartment pharmacokinetic model was presented to elucidate the disposition of HAH and two products, HP and HPH. The parameters used in the model were obtained by administering each of the three compounds (10 mg/kg) separately. The proposed model described the experimental data well and the model parameters were close to the model-independent values. After HP administration, HPH appeared rapidly in plasma, but the HPH availability from HP amounted to only 17.8 +/- 3.7%, based on the comparison between the area under the plasma concentration curves of formed and iv HPH. The formation of HP from HAH in the systemic circulation was demonstrated, but formed HP disappeared rapidly. The fraction of HAH available to the systemic circulation as HPH was extremely low (7.8 +/- 2.2%), indicating that the conversion of HAH to HP was not so extensive. The present results support the hypotheses that HPH is formed via the direct reaction of HAH with pyruvic acid and that the secondary formation is mediated by conversion to HP.

Animals↗
PubMed1984

Excretion of alpha-keto acids by strains of Streptomyces venezuelae.

Cultures of Streptomyces venezuelae released acidic metabolites during nitrogen-limited growth on glucose. The main products were pyruvic acid and alpha-ketoglutaric acid. Variation in the extent of acid production was observed; spores of the parental strain 13s gave approximately 10% of low-producing colonies when plated on acid-base indicator medium. Examination of one low producer, strain PC 51-5, showed that differences in acid production became apparent only in low-glucose media containing manganese. In both strains PC 51-5 and 13s, uptake of alpha-keto-[5-14C]glutaric acid occurred by diffusion and no marked differences in permeability to alpha-ketoglutarate were detected. However, differences were observed in the activity of alpha-ketoglutarate dehydrogenase. In cultures of strain PC 51-5, the specific activity of the enzyme increased throughout growth, whereas in the parental strain activity decreased and could not be detected in older mycelium. Loss of enzyme activity was accompanied by excretion of alpha-ketoglutaric acid and failure to assimilate the product after glucose exhaustion. The results suggest that accumulation of pyruvic and alpha-ketoglutaric acids in S. venezuelae cultures grown in glucose-containing media may be due to regulatory suppression of the dehydrogenases by this carbon source.

Cell Membrane Permeability↗
PubMed1996

Characterization of two new matrices for matrix-assisted laser desorption/ionization mass spectrometry.

Three structurally related compounds, 4-hydroxy-33-methoxyphenylpyruvic acid (HMPPA), indole-3 pyruvic acid (IPA), and indole-3-glyoxylic acid have been evaluated as matrix-assisted laser desorption/ionization (MALDI) matrices. HMPPA and IPA were found to be effective matrices for MALDI-MS analysis of proteins and peptides and have been characterized in this work. HMPPA was found to be a particularly good matrix for the analysis of proteins and peptides because of its tolerance towards impurities and the resulting sensitivity in MALDI-MS experiments. Analysis of model proteins and peptides, including those in biological fluid, are demonstrated.

Glyoxylates↗
PubMed2005

Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection.

A high-performance method of capillary micellar electrokinetic chromatography (CMEKC) with amperometric detection (AD), using a newly designed pre-aligned electrochemical cell, has been developed for the separation and determination of L-tryptophan (Trp) and its eight metabolites including 3-hydroxy-L-kynurenine (3-HK), 5-hydroxy-L-tryptophan (5-HTP), L-kynurenine (KN), 5-hydroxyindole-3-acetic acid (5-HIAA), xanthurenic acid (XA), indole-3-pyruvic acid (IPA), 5-hydroxytryptamine (5-HT), and tryptamine (Tryp). A carbon disk electrode was used as the working electrode and the optimal detection potential was 0.85 V (versus Ag/AgCl). At 24 kV of applied voltage, the nine compounds were completely separated, within 23 min, in a 10 mol/L Na(2)HPO(4)-NaOH buffer (pH 11.0) containing 40 mmol/L sodium dodecyl sulfate (SDS) and 3% methanol (v/v). A good linear relationship was obtained for all analytes in this paper and the detection limits of 3-HK, 5-HTP, KN, Trp, 5-HIAA, XA, IPA, 5-HT, and Tryp were 7.42, 5.18, 34.6, 3.99, 15.1, 12.7, 260, 6.72, and 8.01 nmol/L, respectively. This method has been applied to analyze the metabolism of Trp in rabbit urine.

Animals↗
PubMed1999

Radical scavenging properties of tryptophan metabolites. Estimation of their radical reactivity.

Radical scavenging properties of tryptophan metabolites were estimated using their radical reactivity. Metabolites of the kynurenine and the melatonin biosynthesis pathway were mainly examined by use of a kinetical model. Their radical reactivity was determined as the reaction rate constant with a stable free radical, such as galvinoxyl; that is a phenoxy radical. The rate constants of the metabolites have a widely ranged spectrum, which can be divided into three groups. The first group (3-hydroxykynurenine, 3-hydroxyanthranilic acid, and indole-3-pyruvic acid) is more reactive than alpha-tocopherol; the reactivity of the second group (xanthurenic acid, serotonin, N-acetylserotonin) is similar to that of butylated hydroxytoluene (BHT); the third group (kynurenic acid, melatonin, and other ones) is less reactive than BHT.

Free Radical Scavengers↗
PubMed1999

Off-flavor compounds in wine and other food products formed by enzymatical, physical, and chemical degradation of tryptophan and its metabolites.

Tryptophan (TRP) and its metabolites are considered as potential precursors of 2-aminoacetophenone (AAP) in different food products causing different off-flavors. AAP is also responsible for the "untypical aging flavor (UTA)" in wine, developing a floor polish-like flavor in white wines within a few months of storage. In this study the formation of AAP was elucidated by GC-MS analysis of volatile components in model systems, grape musts and wines, spiked with TRP and different TRP metabolites like indole-3-acetic acid (IAA) and sulfite. In sulfurized wines and model solutions which were stored at different temperatures (20 degrees C, 45 degrees C) formylaminoacetophenone (FAP) and AAP were formed mainly from IAA with formation rates up to 20 mole%. Minor formation rates of AAP (< 1 mole%) were found in sulfurized solutions of TRP, indole-3-lactic acid, and indole-3-pyruvic acid. The results showed that the formation of AAP in wine can be referred to an oxidative degradation of IAA by superoxide- and hydroxyl-radicals, which can be formed in wine after the sulfuration by cooxidation of sulfite to sulfate. After decarboxylation, pyrrole oxidation, and ring cleavage, FAP was the main volatile compound of the nonenzymatic degradation of IAA by sulfite which was quantitatively hydrolyzed to AAP. The formation of AAP and FAP was significantly lower in white wines than in ethanolic solutions spiked with IAA. However AAP formation rates of up to 5 mole% were still enough for an UTA. Due to the fact that the AAP- and UTA-formation by cooxidation of sulfite and IAA was completely blocked in red wines, it could be deduced that polyphenolic compounds, typical for red wines, have a scavenger effect on the radical oxidation of sulfite. Possibilities for an inhibition of the IAA degradation during winemaking to avoid the UTA in white wines by addition of radical scavengers like grape marc or ascorbic acid are discussed.

Acetophenones↗
PubMed1988

Effects of ribamidine, a 3-carboxamidine derivative of ribavirin, on experimentally induced Phlebovirus infections.

Ribamidine (1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine) was inhibitory in rhesus monkey kidney (LLC-MK2 derivative) cells to Adames and Balliet strains of Punta Toro virus (PTV), a Phlebovirus related to Rift Valley fever and sandfly fever viruses. The 50% effective dose was 8 and 12 micrograms/ml against each respective virus strain; the 50% cytotoxic dose was 320 micrograms/ml, giving selectivity indices of 40 and 27 against each virus strain. The virus ratings were 1.2 and 1.0, respectively. In radiolabel uptake studies, ribamidine had a moderate effect on [3H]leucine uptake at dosages down to 1 microgram/ml, but [3H]thymidine, [32P], and [3H]uridine were inhibited at high (100-1000 micrograms/ml) doses only. Subcutaneous (s.c.) and oral treatments of Adames PTV-infected mice were equally highly effective, as evidenced particularly by 100% survivors. Reduced hepatic icterus, serum oxalic acid transaminase, serum glutamic pyruvic acid transaminase, and recoverable virus titers from livers and sera of infected mice were also seen as a result of ribamidine treatment. Twice daily treatment for 5 days could be started as late as 72 h post-virus inoculation (p.v.i.) with significant inhibition of PTV infection seen. Single s.c. treatments administered as late as 48 h p.v.i. were similarly effective. Using the chronic therapy schedule, the maximum tolerated dose was 1000 mg/kg/day and the minimum effective dose was 31.3 to 62.5 mg/kg/day. Using single treatment, a maximum tolerated dose was greater than 1000 mg/kg, and the minimum effective dose was 125 mg/kg. Ribamidine s.c. treatment of mice infected intracerebrally with the Balliet strain of PTV resulted in a moderate infection-inhibitory effect, seen especially by reduced virus titers in the brains of the infected, treated mice.

Administration, Oral↗