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PubMedDate not supplied

On the effect of aliphatic saturated dicarboxylic acids on anaerobic glycolysis in chicken embryo.

Oxalic, succinic, glutaric and pimelic acid (5 mM) had no effect on lactate formation from glucose if added to a crude extract of chicken embryo at the same time as substrate and cofactors; conversely malonic, adipic, suberic, azelaic and sebacic acid had an inhibitory effect ranging from 20% to 35%. When the enzyme preparation was pre-incubated with the dicarboxylic acids for one hour before beginning the experiments, all compounds tested, with the exception of succinate, inhibited anaerobic glycolysis. Hexokinase activity was significantly reduced by saturated dicarboxylic acids from C3 to C10, but not by oxalic acid. Phosphofructokinase was inhibited only by oxalic, pimelic and suberic acid. Pyruvate kinase appeared sensitive only to oxalic acid (64% inhibition).

Anaerobiosis↗
PubMed1980

Synthesis of pimeloyl coenzyme A.

Synthesis of pimeloyl CoA based on the reaction of N-hydroxysuccinimide ester of pimelic acid and coenzyme A in the presence of sodium hydroxide is reported. The CoA derivative has been isolated, purified and fully characterized from its chemical properties and spectral data. The yields are superior to acid chloride, anhydride or ester exchange methods due to lack of side reactions.

Acyl Coenzyme A↗
PubMed1977

Rat urinary metabolites of [9,10-methylene-14C] sterculic acid.

1. The metabolism of [9,10-methylene-14C] sterculic acid was studied in corn oil and Stercula foetida oil fed rats. The majority of the radioactivity was excreted into the urine as short chain dicarboxylic acids. The main urinary metabolites were cis-3,4-methylene adipic acid, cis-3,4-methylene suberic acid, trans-3,4-methylene adipic acid, cis-3,4-methylene pimelic acid, and cis-3,4-methylene azelic acid. 2. Formation of these urinary metabolites requires alpha-, beta-, and omega-oxidation plus reduction of the cyclopropene ring to a cyclopropane ring. Sterculic acid must be transported through both mitochondrial and microsomal systems. 3. Other non-radioactive urinary compounds were also identified. A proposed pathway for the metabolism of sterculic acid and possible detrimental effects caused by these metabolites is discussed.

Animals↗
PubMed1984

Metabolism of alpha-terpineol by Pseudomonas incognita.

Details of the metabolism of alpha-terpineol by Pseudomonas incognita are presented. Degradation of alpha-terpineol by this organism resulted in the formation of a number of acidic and neutral metabolites. Among the acidic metabolites, beta-isopropyl pimelic acid, 1-hydroxy-4-isopropenyl-cyclohexane-1-carboxylic acid, 8-hydroxycumic acid, oleuropeic acid, cumic acid, and p-isopropenyl benzoic acid have been identified. Neutral metabolites identified were limonene, p-cymene-8-ol, 2-hydroxycineole, and uroterpenol. Cell-free extracts prepared from alpha-terpineol adapted cells were shown to convert alpha-terpineol, p-cymene-8-ol, and limonene to oleuropeic acid, 8-hydroxycumic acid, and perillic acid, respectively, in the presence of NADH. The same cell-free extract contained NAD+ -specific dehydrogenase(s) which converted oleuropyl alcohol, p-cymene-7,8-diol, and perillyl alcohol to their corresponding 7-carboxy acids. On the basis of various metabolites isolated from the culture medium, together with the supporting evidence obtained from enzymatic and growth studies, it appears that P. incognita degrades alpha-terpineol by at least three different routes. While one of the pathways seems to operate via oleuropeic acid, a second may be initiated through the aromatization of alpha-terpineol. The third pathway may involve the formation of limonene from alpha-terpineol and its further metabolism.

Chromatography, Gas↗
PubMed1986

The analysis of thiodiglycollic acid by selected ion monitoring.

A selected ion monitoring assay for thiodiglycollic acid in urine is described. Urine samples are analysed by combined gas chromatography-mass spectrometry as their dibutyl esters using pimelic acid as an internal standard. Rapid analysis was achieved by the simplification of sample preparation. The assay has proved to be reliable, with a detection limit of less than 0.5 mumol/l. The excretion of large amounts of thiodiglycollic acid in premature babies urine has been confirmed, with the greatest excretion occurring from those neonates born with a gestational age of 30 wk or less.

Gas Chromatography-Mass Spectrometry↗
PubMed1985

Biosynthesis of biotin-vitamers from unsaturated higher fatty acids by bacteria.

The biosynthesis of biotin-vitamers from unsaturated higher fatty acids by the resting cell system of bacteria was investigated. Biotin-vitamer formation from oleic, linoleic and linolenic acids was found in certain bacteria belonging to the genera Enterobacter, Agrobacterium, Bacillus, Escherichia and Micrococcus. The biotin-vitamers were identified as a mixture of 7,8-diaminopelargonic acid, desthiobiotin and biotin. Metabolites other than biotin-vitamers from those fatty acids were analyzed by gas-liquid chromatography and mass spectrometry. Linoleic, oleic, C-17 and C-15 saturated fatty acids were identified as the main metabolites of linolenic acid. The pathway of biosynthesis of pimelic acid from linolenic acid by a strain of Bacillus sphaericus AKU 0227 was also studied.

Bacillus↗
PubMed1973

The direction of glycan synthesis in a bacterial peptidoglycan.

A cell-free membrane preparation from a poorly lytic mutant of Bacillus licheniformis was used to synthesize radioactive peptidoglycan. The product was apparently un-cross-linked. When UDP-N-acetyl[(14)C]glucosamine was used and the final peptidoglycan subjected to Smith degradation, no radioactive glycerol was found. On the other hand, when peptidoglycan labelled with meso-diamino[(14)C]pimelic acid was first hydrolysed in 0.1m-HCl at 60 degrees C for 2h and then subjected to alkaline conditions, radioactive lactyl-peptides were eliminated. The proportion of radioactive lactyl-peptide decreased with increasing time of incorporation. It is concluded that the glycan chains grow by extension at their reducing ends while remaining attached by some linkage labile to mild acid, such as a glycosyl link to undecaprenol pyrophosphate.

Amino Acids, Diamino↗
PubMed1965

INTERACTION OF ASPARTATE AMINOTRANSFERASE WITH AMINO ACIDS.

1. The capacity of various amino acids to convert the pyridoxal form of aspartate aminotransferase into the pyridoxamine form has been investigated. 2. Glutamate has the highest converting capacity; aspartate, alpha-aminopimelate, alpha-aminoadipate and other amino acids follow. 3. The converting capacity of the various amino acids assayed is connected with their structural features. 4. A possible role of amino acids as secondary substrates of aspartate aminotransferase is suggested.

Adipates↗
PubMed1969

Biological studies with alpha-dehydrobiotin.

A growing culture of Streptomyces lydicus converted biotin-(14)C to alpha-dehydrobiotin-(14)C. The conversion was demonstrated by isolating crystalline alpha-dehydrobiotin-(14)C from fermentation liquors supplemented with biotin-(14)C. The addition of pimelic acid-(14)C to the growing culture did not produce any radioactive alpha-dehydrobiotin. alpha-Dehydrobiotin did not substitute for biotin in Lactobacillus plantarum or in Saccharomyces cerevisiae. Antimicrobial activity of alpha-dehydrobiotin was abolished by avidin. alpha-Dehydrobiotin appears to be different from several biotin vitamers described in the literature. It is concluded that alpha-dehydrobiotin is a product of biotin catabolism in S. lydicus.

Biotin↗
PubMed2006

Biological significance and development of practical synthesis of biotin.

Biotin (1), a water-soluble B series vitamin, distributes widely in microorganisms, plants, and animals. Biosynthesis of 1 involves five steps sequence starting from pimelic acid. The last step, a transformation from dethiobiotin (DTB) to 1, includes an iron clusters-mediated radical process. The compound 1 is a cofactor of carboxylation enzymes and plays crucial roles in the metabolism of fatty acids, sugars, and alpha-amino acids. In addition to the increasing application to feed additives, recent reports have revealed that 1 enhances insulin secretion in animals, suggesting it for a promising therapeutic candidate for an anti-diabetes drug. The remarkably strong affinity of 1 with avidin and streptavidin has been extensively applied for such technologies as photoaffinity labeling. Among the number of approaches to 1 so far developed in 50 years, a synthesis using L-cysteine and thiolactone as a starting material and a key intermediate, respectively, represents one of the best routes leading to 1, because of short steps, high yield, use of inexpensive reagents, and ease of operation.

Animals↗
PubMed2001

Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates.

Crystallization of 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (1), previously found to produce six conformational polymorphs from solution, on single-crystal pimelic acid (PA) substrates results in selective and oriented growth of the metastable "YN" (yellow needle) polymorph on the (101)(PA) faces of the substrate. Though the freshly cleaved substrate crystals expose (101)(PA) and (111)(PA) faces, which are both decorated with [101](PA) ledges that could serve as nucleation sites, crystal growth of YN occurs on only (101)(PA). Goniometry measurements performed with an atomic force microscope reveal that the (001)(YN) plane contacts (101)(PA) with a crystal orientation [100](YN)//[010](PA) and [010](YN)//[101](PA). A geometric lattice analysis using a newly developed program dubbed GRACE (geometric real-space analysis of crystal epitaxy) indicates that this interfacial configuration arises from optimal two-dimensional epitaxy and that among the six polymorphs of 1, only the YN polymorph, in the observed orientation, achieves reasonable epitaxial match to (101)(PA). The geometric analysis also reveals that none of the polymorphs, including YN, can achieve comparable epitaxial match with (111)(PA), consistent with the absence of nucleation on this crystal face. In contrast, sublimation of 1 on cleaved succinic acid (SA) substrates, which expose large (010)(SA) faces decorated with steps along [101](SA), affords growth of several polymorphs, each with multiple orientations, as well as oriented crystals of a new metastable polymorph on the (010)(SA) surfaces. The lack of polymorphic selectivity on (010)(SA) can be explained by the geometric lattice analysis, which reveals low-grade epitaxial matches between (010)(SA) and several polymorphs of 1 but no inherent selectivity toward a single polymorph. These observations demonstrate the sensitivity of crystal nucleation to substrate surface structure, the potential of crystalline substrates for selective nucleation and discovery of polymorphs, and the utility of geometric lattice modeling for screening of substrate libraries for controlling polymorphism.

Benzodiazepines↗
PubMed1994

Anaerobic degradation of pimelate by newly isolated denitrifying bacteria.

A C7 dicarboxylic (pimelic) acid derivative is postulated as an intermediate in anaerobic degradation of benzoate. Four strains of Gram-negative, nitrate-reducing bacteria capable of growth with both pimelate and benzoate as sole carbon and energy source were isolated. The metabolism of strain LP-1, which was enriched from activated sludge with pimelate as substrate, was studied in detail. This strain grew only with oxygen or with oxidized nitrogen compounds as electron acceptor. In the presence of nitrate, a wide range of substrates excluding C1 compounds was degraded. The new isolate was catalase- and oxidase-positive, and had one single polar flagellum. Strain LP-1 was tentatively classified within the family Pseudomonadaceae. The catabolism of pimelate and benzoate was studied in cell-free extracts of strain LP-1. Both acids were activated with coenzyme A in a Mg(2E)- and ATP-dependent reaction. The corresponding acyl-CoA synthetases were specifically induced by the respective growth substrate. Pimelate was also activated by CoA transfer from succinyl-CoA. Pimelyl-CoA was oxidized by cell-free extracts in the presence of potassium ferricyanide. Degradation to glutaryl-CoA and acetyl-CoA proceeded by a sequence of beta-oxidation-like reactions. Glutaryl-CoA dehydrogenase and glutaconyl-CoA decarboxylase activities were expressed in cells grown with pimelate or benzoate, indicating the specific involvement of these enzyme activities in anaerobic degradation of these two acids. Enzyme activities responsible for further degradation of the resulting crotonyl-CoA to acetyl-CoA via classical beta-oxidation were also detected.

Anaerobiosis↗
PubMed1985

[Protein and amino acid metabolism in the digestive tract growing young bulls. 1. Flow of bacterial raw protein in the duodenum determined by 2,6-diaminopimelic acid as a marker].

The influence of the composition of the rations on the content of diamino pimelic acid (DAP) and N in the bacteria dry matter and on the flow of bacteria crude protein into the duodenum, determined with DAP as marker, was determined on the basis of experimental investigations with young bulls provided with duodenal cannulae and with 28 different rations whose details are described. At a production level corresponding to dry matter intake and a variation range of the crude fibre content of between 11.3 and 29.1% in the DM, a content of N-free extractives between 50.9 and 77.4% in the DM, a content of soluble carbohydrates ibetween 5.3 and 6.4% in the DM, a crude protein content of between 6.4 and 17.1% in the DM and a pure protein content of between 4.9 and 15.5% in the DM, the DAP content of the bacteria DM amounts the 0.350 g 100 g DM +/- 0.090 the N-content of the bacteria DM amounts to 7.37 +/- 1.08 g/100 g DM, there are no relations between DAP- and N-content in the bacteria DM and the content of the individual carbohydrate fractions of the ration, there are positive relations between DAP- and N-content of the bacteria DM, the flow of bacterial crude protein into the duodenum amounts to 133 +/- 14 g/kg truly fermentable organic matter or 130 +/- 14 g/kg apparently digestible organic matter, there is a negative relation between bacteria crude protein at the duodenum (BCPD)/kg truly fermentable organic matter and the crude fibre content of the ration, there is a positive relation between BCPD/kg truly fermentable organic matter and N-free extractives and soluble carbohydrate content as well as the digestibility of the organic matter of the ration, there is no specific influence of the flow rate (kg digesta/kg intake of org. matter) or the dilution rate (g bacteriafree org. matter D/kg LW075/b) on BCPD/kg truly fermentable org. matter, there is a dependence of BCPD/kg truly fermentable org. matter on crude protein concentration in the ration in the concentration range of 6.4-9.0% crude protein in the ration (provided endogenous CP equivalents are used).

Amino Acids↗
PubMed2005

X-ray studies on crystalline complexes involving amino acids and peptides. XLII. Adipic acid complexes of L- and DL-arginine and supramolecular association in arginine-dicarboxylic acid complexes.

The adipic acid complexes of DL-arginine and L-arginine are made up of zwitterionic, singularly positively charged arginium ions and doubly negatively charged adipate ions, with a 2:1 stoichiometry. One of the two crystallographically independent arginium ions in the L-arginine complex has a conformation hitherto unobserved in crystal structures containing the amino acid. In the present study the structural data on arginine complexes of saturated dicarboxylic acids with 0-5 C atoms separating the two carboxyl functions are given. In terms of molecular aggregation, formic and acetic acid complexes behave in a similar way to those involving fairly long carboxylic acids such as adipic acid. By and large, the supramolecular assembly in complexes involving dicarboxylic acids with 3 or more C atoms separating the carboxyl groups (glutaric, adipic and pimelic acids), and those involving formic and acetic acids, have common features. The aggregation patterns in complexes involving oxalic, malonic and maleic acids do not share striking features among themselves (except for the mode of hydrogen-bonded dimerization of arginium ions) or with those involving larger dicarboxylic acids. Complexes of succinic acid, the shortest linear dicarboxylic acid, share features with those involving shorter as well as longer dicarboxylic acids. The difference in the behaviour of long and short dicarboxylic acids and the ambiguous behaviour of succinic acid can be broadly related to their lengths.

Adipates↗
PubMed1989

In vitro metabolism of 2,2'-diaminopimelic acid from gram-positive and gram-negative bacterial cells by ruminal protozoa and bacteria.

Bacillus megaterium GW1 and Escherichia coli W7-M5 were specifically radiolabeled with 2,2'-diamino[G-3H]pimelic acid [( 3H]DAP) as models of gram-positive and gram-negative bacteria, respectively. These radiolabeled bacterial mutants were incubated alone (control) and with mixed ruminal bacteria or protozoa, and the metabolic processes, rates, and patterns of radiolabeled products released from them were studied. Control incubations revealed an inherent difference between the two substrates; gram-positive supernatants consistently contained 5% radioactivity, whereas even at 0 h, those from the gram-negative mutant released 22%. Incubations with ruminal microorganisms showed that the two mutants were metabolized differently and that protozoa were the major effectors of their metabolism. Protozoa exhibited differential rates of engulfment (150 B. megaterium GW1 and 4,290 E. coli W7-M5 organisms per protozoan per h), and they extensively degraded [3H]DAP-labeled B. megaterium GW1 at rates up to nine times greater than those of ruminal bacteria. By contrast, [3H]DAP-labeled E. coli W7-M5 degradation by either ruminal bacteria or ruminal protozoa was more limited. These fundamental differences in the metabolism of the two mutants, especially by ruminal protozoa, were reflected in the patterns and rates of radiolabeled metabolites produced; many were rapidly released from [3H]DAP-labeled B. megaterium GW1, whereas few were slowly released from [3H]DAP-labeled E. coli W7-M5. Most radiolabeled products derived from [3H]DAP-labeled B. megaterium GW1 were peptides of bacterial peptidoglycan origin. The ruminal metabolism of DAP-containing gram-positive and gram-negative bacteria, even with the same peptidoglycan chemotype, is thus likely to be profoundly different.(ABSTRACT TRUNCATED AT 250 WORDS)

Amino Acids, Diamino↗
PubMed1991

In vivo metabolism of 2,2'-diaminopimelic acid from gram-positive and gram-negative bacterial cells by ruminal microorganisms and ruminants and its use as a marker of bacterial biomass.

Cells of Bacillus megaterium GW1 and Escherichia coli W7-M5 were specifically radiolabeled with 2,2'-diamino[G-3H]pimelic acid ([3H]DAP) as models of gram-positive and gram-negative bacteria, respectively. Two experiments were conducted to study the in vivo metabolism of 2,2'-diaminopimelic acid (DAP) in sheep. In experiment 1, cells of [3H]DAP-labeled B. megaterium GW1 were infused into the rumen of one sheep and the radiolabel was traced within microbial samples, digesta, and the whole animal. Bacterially bound [3H]DAP was extensively metabolized, primarily (up to 70% after 8 h) via decarboxylation to [3H]lysine by both ruminal protozoa and ruminal bacteria. Recovery of infused radiolabel in urine and feces was low (42% after 96 h) and perhaps indicative of further metabolism by the host animal. In experiment 2, [3H]DAP-labeled B. megaterium GW1 was infused into the rumens of three sheep and [3H]DAP-labeled E. coli W7-M5 was infused into the rumen of another sheep. The radioactivity contents of these mutant bacteria were insufficient to use as tracers, but the metabolism of DAP was monitored in the total, free, and peptidyl forms. Free DAP, as a proportion of total DAP in duodenal digesta, varied from 0 to 9.5%, whereas peptidyl DAP accounted for 8.3 to 99.2%. These data reflect the extensive metabolism of bacterially bound DAP within the gastrointestinal tracts of ruminant animals and serve as a serious caution to the uncritical use of DAP as a marker of bacterial biomass in the digesta of these animals.

Animals↗
PubMedDate not supplied

[Amino acid composition of the fecal bacteria in the pig].

The composition of amino acids in faecal bacteria of pigs is described. A total of 15 faeces samples from experiments with three different rations was assessed. The conversion factor 26.1 for the calculation of bacteria-N from the content of 2.6 diamino pimelic acid is stated.

Amino Acids↗