Gene/Protein Disease Symptom Drug Enzyme Compound
Pivot Concepts:   Target Concepts:
Query: CAS:638-53-9 (tridecanoic acid)
 65 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Using a Yarrowia lipolytica genomic library, several overlapping clones of the peroxisomal 3-oxoacyl-CoA-thiolase gene, POT1, were isolated. The library was prepared in the bacterial expression vector lambda gt11, thus allowing an immunological screening of recombinant bacteriophages with specific antibodies raised against purified peroxisomal thiolase. The isolated POT1 clones hybridized to a 1.4 kb RNA species, which was induced approximately 30-fold when oleate was the carbon source. A 3634-bp segment of the cloned DNA was sequenced. This segment contained, on both strands, three major overlapping open-reading frames of 678, 1122 and 1242 bp. Northern-hybridization analysis showed that only the largest of these reading frames was transcribed. It encodes a protein of 414 amino acids and molecular mass 43.059 kDa. Its deduced amino acid sequence has 30-60% identity and 50-70% sequence similarity when compared to other known thiolases. According to both the amount (68-71%) and location of conserved amino acids, the encoded protein belongs to the peroxisomal rather than the mitochondrial or cytoplasmic class of thiolases. Compared to bacterial and yeast cytosolic thiolases, the POT1 gene product contains a N-terminal extension of 25 amino acids which clearly differs from typical mitochondrial import signals. One of the isolated clones contained, in addition to the POT1 coding sequence, 784 bp of the corresponding 5' flanking region. Nevertheless, it was efficiently expressed in Escherichia coli suggesting the correct recognition of this fungal promoter by the prokaryotic transcriptional and translational machinery. The Y. lipolytica genomic POT1 gene was disrupted by replacing 120 bp of its coding sequence with 2.7 kbp of DNA including the Y. lipolytica LEU2 gene. The resulting delta pot1::LEU2 cells were free of immunologically cross-reacting thiolase. Western-blot analysis showed that the product of the non-disrupted gene had a molecular mass of approximately 42 kDa. This corresponds well to the molecular mass of purified Y. lipolytica peroxisomal thiolase. Disruption of POT1 abolished the ability of Y. lipolytica cells to grow on solid media with oleate as a carbon source. This inability to grow in the presence of oleate suggests both the catabolic function of POT1 and the absence of additional catabolic thiolases in Y. lipolytica. However, the delta pot1::LEU2 cells were unaffected in their ability to elongate externally added tridecanoic acid to its higher-chain-length homologues. Hence, another, POT1-independent and biosynthetic 3-oxoacyl-CoA thiolase must be responsible for this reaction in Y. lipolytica.
 ...
PMID:Structure and metabolic control of the Yarrowia lipolytica peroxisomal 3-oxoacyl-CoA-thiolase gene. 791 89

The chemical structure of the lipid A components of smooth-type lipopolysaccharides isolated from the type strains of strictly anaerobic beer-spoilage bacteria Pectinatus cerevisiiphilus and Pectinatus frisingensis were analyzed. The hydrophilic backbone of lipid A was shown, by controlled degradation of lipopolysaccharide combined with chemical assays and 31P-NMR spectroscopy, to consist of the common beta 1-6-linked disaccharide of pyranosidic 2-deoxy-glucosamine (GlcN), phosphorylated at the glycosidic position and at position 4'. In de-O-acylated lipopolysaccharide, the latter phosphate was shown to be quantitatively substituted with 4-amino-4-deoxyarabinose, whereas the glycosidically linked phosphate was present as a monoester. Laser-desorption mass spectrometry of free dephosphorylated lipid A revealed that the distal (non-reducing) GlcN was substituted at positions 2' and 3' with (R)-3-(undecanoyloxy)tridecanoic acid, whereas the reducing GlcN carried two unsubstituted (R)-3-hydroxytetradecanoic acids at positions 2 and 3. The lipid A of both Pectinatus species were thus of the asymmetric hexaacyl type. The linkage of lipid A to polysaccharide in the lipopolysaccharide was relatively resistant to acid-catalyzed hydrolysis, enabling the preparation of a dephosphorylated and deacylated saccharide backbone. Methylation analysis of the backbone revealed that position 6' of the distal GlcN of lipid A was the attachment site of the polysaccharide. Despite the quantitative substitution of the lipid A 4'-phosphate by 4-amino-4-deoxyarabinose, which theoretically should render the bacteria resistant to polymyxin, P. cerevisiiphilus was shown to be susceptible to this antibiotic. P. cerevisiiphilus was, however, also susceptibile to vancomycin and bacitracin, indicating that the outer membrane of this bacterium does not act as an effective permeability barrier.
 ...
PMID:Chemical structure of the lipid A component of lipopolysaccharides of the genus Pectinatus. 807 52

Since the oxidation of long chain fatty acids is the major pathway for energy production for the normoxic myocardium, the use of radiolabeled fatty acids for myocardial imaging continues to be a major area of both basic and clinical research. This paper focuses on a discussion of the kinetics of myocardial uptake of radioiodinated fatty acids, including planar and SPECT imaging of various iodine-123-labeled analogues, and data from animal and isolated heart studies, and where possible, comparison with results of clinical studies. Key examples include iodoalkyl-substituted straight chain fatty acids such as 17-IHDA (17-iodoheptadecanoic acid). These analogues are rapidly metabolized in the myocardium, resulting in release of free radioiodide, and can only be practically used for planar imaging. Terminal iodophenyl-substituted fatty acids illustrate a successful approach of stabilizing radioiodine to overcome the release of free iodide encountered with the straight-chain analogues. These analogues, exemplified by p-IPPA [15-(p-iodophenyl)pentadecanoic acid], are widely used in clinical practice. Although washout can be delayed by increase in the arterial lactate levels by mild exercise, SPECT imaging must still be carefully timed. In contrast to these examples, the ortho iodide-substituted IPPA isomer (ortho- instead of para-phenyl substitution of radioiodide) is a unique example which shows rapid myocardial washout in laboratory animals but nearly irreversible retention in humans. Introduction of methyl-branching is a major important approach which has been successfully used to alter tracer kinetics of radioiodinated fatty acids by increasing myocardial retention. A key example in this class of compounds is 3-(R,S)-BMIPP [15-(p-iodophenyl)-3-(R,S)-methylpentadecanoic acid], an analogue of p-IPPA in which methyl-branching has been introduced into the beta-position of the carbon chain. Although tracer washout is significantly delayed with this structural perturbation, a large number of clinical studies have shown that slow myocardial washout is still observed. Detailed biochemical studies with radioiodinated 3-BMIPP have demonstrated that initial alpha-oxidation produces a metabolite that can then be catabolized by alpha-oxidation. An unexpected and important observation with the (123I]-3-(R,S)-BMIPP agent has been the mis-match between perfusion tracer distribution and the regional BMIPP distribution which has been widely observed in jeopardized, but viable myocardial regions. Another example in the methyl-branched series is DMIPP [15-(p-iodophenyl)- 3,3-dimethylpentadecanoic acid], which has very prolonged myocardial retention and slow washout kinetics although only animal studies have been reported with this agent. Still another more recent approach has been the synthesis and laboratory animal and human evaluation of analogues containing a phenylene bridge in the fatty acid chain. One example is 3-10 [13-(4'-iodophenyl)]-3-(p-phenylene)tridecanoic acid (PHIPA 3-10), which has also proven successful in delaying myocardial tracer washout. This paper focuses on a discussion of the effects of molecular structure on the myocardial uptake and release of these various radioiodinated fatty acid analogues.
 ...
PMID:Pharmacokinetics of radioiodinated fatty acid myocardial imaging agents in animal models and human studies. 896 3

Chemical and biological studies were performed on lipopolysaccharide isolated from Selenomonas sputigena ATCC 33150T, a possible causative agent of periodontal diseases. The sugar components of the lipopolysaccharide of S. sputigena were mannose, galactose, glucose, L-glycero-D-mannoheptose (heptose), 2-keto-3-deoxy-octonic acid, glucosamine and galactosamine in a molar ratio of 0.3:1.0:1.0:1.0:0.2:3.0:3.2 (mol/mol heptose). Sephadex G-50 chromatography of the polysaccharide portion of the lipopolysaccharide obtained by partial hydrolysis yielded three fractions: the O-polysaccharide chain attached to the core oligosaccharide, the core oligosaccharide and monosaccharides. Compositional analysis of these fractions revealed that lipopolysaccharide of S. sputigena carries a short O-polysaccharide chain consisting of galactose and glucosamine and that the core oligosaccharide consisted of glucose, heptose, glucosamine and 2-keto-3-deoxyoctonic acid. It is of particular interest that galactosamine was detected as a component sugar of the lipid A moiety in addition to glucosamine, which is a usual component sugar of the lipid A of most gram-negative bacteria. Thus, the lipid A of S. sputigena might have a unique backbone that differs from that of the lipid A of other gram-negative bacteria. Lipid A of S. sputigena consisted mainly of fatty acids such as undecanoic, tridecanoic, tridecenoic, 3-hydroxytridecanoic and 3-hydroxytetradecanoic acid in a molar ratio of 0.4:1.0:0.3:4.0:0.5 (mol/mol tridecanoic acid). Lipopolysaccharide and lipid A from S. sputigena both exhibited biological activity in activating the clotting enzyme of Limulus amebocytes, the Schwartzman reaction, mitogenicity for murine lymphocytes and in inducing interleukin-1 alpha and interleukin-6 production in murine macrophages to the same extent as those observed for lipopolysaccharide of the Salmonella serovar typhimurium used as a positive control. The results suggested that the lipopolysaccharide of S. sputigena is a virulent factor in human periodontal diseases.
 ...
PMID:Chemical and biological properties of lipopolysaccharide from Selenomonas sputigena ATCC 33150. 946 2

This peer-verified method specifies a fast, easy, and reliable quantitative method to determine total fat in foods and feeds in compliance with the new definition of fat from the U.S. Food and Drug Administration. The method takes into consideration all fatty acids, from C4 to C24, and when fat is present at 0.3-100%. The validation study included 9 matrixes, with fat levels ranging from 1 to 79%. Sample and internal standard (IS; tridecanoic acid) are added to solvent (n-butyl alcohol). Fat is extracted and simultaneously saponified by potassium hydroxide. The fatty acid potassium salts are converted to fatty acids by adding an acidic aqueous salt solution, which produces a 2-phase system. The upper phase, containing the fatty acids and IS, is injected into the fat determination system. After gas chromatographic separation, the fat content is calculated from IS and fatty acid peak areas. The fat content is automatically converted to triglyceride content with a pre-determined factor. Ten replicates of 9 different food samples, which cover the whole range of different contents in fat, proteins, and carbohydrates, were analyzed by the submitting and the peer laboratories. Repeatability relative standard deviation (RSDr) values ranged from 0.47 to 4.62%. Reproducibility relative standard deviation (RSDR) values ranged from 0.85 to 9.52%. These estimates include between-run variability. The method shows good accuracy. Values for standard reference materials (SRMs) are in agreement with certified values. Regression analysis of the correlation between observed fat and certified value over all matrixes and fat levels indicated good precision and absence of method bias (5 SRMs; 1-30% fat; correlation coefficient, R2 = 99.98%).
 ...
PMID:Determination of total fat in foods and feeds by the caviezel method, based on a gas chromatographic technique. 968 Jul 16

Effects of fatty acids on translocation of the gamma- and epsilon-subspecies of protein kinase C (PKC) in living cells were investigated using their proteins fused with green fluorescent protein (GFP). gamma-PKC-GFP and epsilon-PKC-GFP predominated in the cytoplasm, but only a small amount of gamma-PKC-GFP was found in the nucleus. Except at a high concentration of linoleic acid, all the fatty acids examined induced the translocation of gamma-PKC-GFP from the cytoplasm to the plasma membrane within 30 s with a return to the cytoplasm in 3 min, but they had no effect on gamma-PKC-GFP in the nucleus. Arachidonic and linoleic acids induced slow translocation of epsilon-PKC-GFP from the cytoplasm to the perinuclear region, whereas the other fatty acids (except for palmitic acid) induced rapid translocation to the plasma membrane. The target site of the slower translocation of epsilon-PKC-GFP by arachidonic acid was identified as the Golgi network. The critical concentration of fatty acid that induced translocation varied among the 11 fatty acids tested. In general, a higher concentration was required to induce the translocation of epsilon-PKC-GFP than that of gamma-PKC-GFP, the exceptions being tridecanoic acid, linoleic acid, and arachidonic acid. Furthermore, arachidonic acid and the diacylglycerol analogue (DiC8) had synergistic effects on the translocation of gamma-PKC-GFP. Simultaneous application of arachidonic acid (25 MicroM) and DiC8 (10 microM) elicited a slow, irreversible translocation of gamma-PKC- GFP from the cytoplasm to the plasma membrane after rapid, reversible translocation, but a single application of arachidonic acid or DiC8 at the same concentration induced no translocation. These findings confirm the involvement of fatty acids in the translocation of gamma- and epsilon-PKC, and they also indicate that each subspecies has a specific targeting mechanism that depends on the extracellular signals and that a combination of intracellular activators alters the target site of PKCs.
 ...
PMID:Distinct effects of fatty acids on translocation of gamma- and epsilon-subspecies of protein kinase C. 978 59

Many moth species biosynthesize their sex pheromones by the action of unique desaturases. These membrane-bound family of enzymes are especially interesting, since some of them produce (E)-unsaturated fatty acids either exclusively or along with the (Z)-isomer. In this article we present the first mechanistic study on one of these enzymes, namely, the Delta11-myristoyl-CoA desaturase of the moth Spodoptera littoralis. Intermolecular primary isotope effect determinations were performed in competition experiments. The unusual use of odd-number fatty acids, tridecanoic acid and deuterium-labeled tridecanoic acid, in these experiments showed the existence of a large isotope effect for the carbon-hydrogen bond cleavage at C11, but no isotope discrimination occurred in the removal of C12-H. The results of the competitive experiments are consistent with the hypothesis that this Delta11-desaturase involves a first slow, isotope-sensitive C11-H bond cleavage, with probable formation of an unstable intermediate, followed by a second fast C12-H bond removal. We suggest that a single enzyme may be responsible for the formation of both (Z)- and (E)-11-tetradecenoic acids by accommodating both gauche and anti conformers of the substrate, respectively. It is also possible that two mechanistically identical discrete enzymes are involved in each desaturation. In this case, the geometry of the resulting double bond would result from the different conformation adopted by the acyl substrate at each enzyme active site.
 ...
PMID:Cryptoregiochemistry of the delta11-myristoyl-CoA desaturase involved in the biosynthesis of Spodoptera littoralis sex pheromone. 1056 12

Pseudomonas mendocina strain 0806 was isolated from oil-contaminated soil and found to produce polyesters consisting of medium chain length 3-hydroxyalkanoates (mclPHAs). The monomers of mclPHAs contained even numbers of carbon atoms, such as 3-hydroxyhexanoate (HHx or C6), 3-hydroxyoctanoate (HO or C8), and/or 3-hydroxydecanoate (HD or C10) as major components when grown on many carbon sources unrelated to their monomeric structures, such as glucose, citric acid, and carbon sources related to their monomeric structures, such as myristic acid, octanoate, or oleic acid. On the other hand, PHA containing both even and odd numbers of hydroxyalkanoates (HA) monomers was synthesized when the strain was grown on tridecanoic acid. The molar ratio of carbon to nitrogen (C/N) had a significant effect on PHA composition: the strain produced PHAs containing 97-99% of HD monomer when grown in a glucose ammonium sulfate medium of C/N<20, and 20% HO, and 80% of the HD monomer when growth was conducted in media containing C/N>40. It was demonstrated that the HO/HD ratio in the polymers remained constant in media with a constant C/N ratio, regardless of the glucose concentration. Up to 3.6 g/L cell dry weight containing 45% of PHAs was produced when the strain was grown for 48 h in a medium containing 20 g/L glucose with a C/N ratio of 40.
 ...
PMID:Production of polyesters consisting of medium chain length 3-hydroxyalkanoic acids by Pseudomonas mendocina 0806 from various carbon sources. 1069 75

Moth pheromone glands contain desaturases that catalyze the formation of conjugated dienoic fatty acids. In this article we present the first stereochemical study on one of these enzymes, namely the Delta(9) desaturase of (E)-11-tetradecenoic acid, using the moth Spodoptera littoralis as a biological model and enantiopure deuterated probes derived from tridecanoic acid. Gas chromatography coupled to mass spectrometry analysis of methanolyzed lipidic extracts from glands incubated with each individual probe showed that in the transformation of (E)-11-tetradecenoic acid into (Z,E)-9,11-tetradecadienoic acid both pro-(R) hydrogen atoms at C9 and C10 are removed from the substrate.
 ...
PMID:Stereospecificity of the (Z)-9 desaturase that converts (E)-11-tetradecenoic acid into (Z,E)-9,11-tetradecadienoic acid in the biosynthesis of Spodoptera littoralis sex pheromone. 1137 15

Nocardia globerula strain 432 was able to synthesize triacylglycerols (TAG) during cultivation on 2,6,10,14-tetramethyl pentadecane (pristane) under nitrogen-limiting conditions. Within these cells, 4,8,12-trimethyl tridecanoic acid was the major fatty acid detected. Fatty acids with an odd number of carbon atoms and minor amounts of even-numbered fatty acids were also observed. Experiments carried out with acrylic acid, an inhibitor of beta-oxidation, suggested that odd-numbered fatty acids such as C15:0, C17:0 and 10-methyl C17:0 were synthesized de novo using propionyl-CoA, the beta-oxidation product, as precursor. Although N. globerula 432 incorporated mainly straight chain fatty acids into TAG, the branched fatty acid 4,8,12-trimethyl tridecanoic acid also appeared, to some extent, in the acylglycerols. The importance of TAG biosynthesis by pristane-grown cells of N. globerula strain 432 is discussed.
 ...
PMID:Biosynthesis of fatty acids and triacylglycerols by 2,6,10,14-tetramethyl pentadecane-grown cells of Nocardia globerula 432. 1142 75


<< Previous 1 2 3 4 5 6 Next >>