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Query: CAS:638-53-9 (tridecanoic acid)
 65 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Acholeplasma laidlawii B cells made fatty acid auxotrophic by growth in the presence of the biotin-binding agent avidin grow increasingly poorly at 37 degrees C when supplemented with single exogenous linear saturated fatty acids of decreasing hydrocarbon chain length. Interestingly, this progressive decrease in growth yields with decreasing hydrocarbon chain length is not observed when cells are cultured in the presence of other classes of exogenous fatty acids. Moreover, normal growth is observed is other types of fatty acids with equivalent or shorter hydrocarbon chain lengths, indicating that poor growth in the presence of short-chain linear saturated fatty acids cannot be due to a decrease in membrane lipid bilayer thickness per se. To understand the molecular basis of such growth inhibition, we determined the growth yields, membrane lipid fatty acid and polar headgroups compositions, and phase state and fluidity of the membrane lipids in cells progressively biosynthetically enriched in tridecanoic acid (13:0) or dodecanoic acid (12:0). The growth of fatty acid auxotrophic A. laidlawii B cells grown in the presence of binary combinations of an exogenous fatty acid which supports normal growth on its own and 13:0 or 12:0 revealed that growth inhibition is not observed until 13:0 and 12:0 biosynthetic incorporation levels reach about 90 and 60 mol %, respectively, after which growth is markedly inhibited. Differential scanning calorimetric analyses of membranes from cells maximally enriched in 13:0 indicate that the lipid gel/liquid-crystalline phase transition temperature is unexpectedly high but that at the growth temperature of 37 degrees C, the membrane lipid bilayer is almost exclusively in the liquid-crystalline state but is certainly not excessively fluid. However, high levels of 13:0 incorporation produce a greatly elevated level of the high melting, reversed nonlamellar phase-preferring lipid component monoglucosyl diacylglycerol, and greatly reduced levels of all other membrane lipid components. This marked elevation of monoglucosyl diacylglycerol levels can be rationalized as a regulatory response which maintains the lamellar/nonlamellar phase-forming propensity of the total membrane lipid mixture relatively constant in the face of the biosynthetic incorporation of increasing quantities of short-chain saturated fatty acids, which favor the lamellar phase. However, this lipid biosynthetic response produces a marked decline in the levels of anionic phospholipid and phosphoglycolipid which are probably required to maintain the minimal negative surface charge density of the lipid bilayer, which we suggest is responsible for the observed growth inhibition. This work shows that the lipid biosynthetic regulatory mechanisms present in this organism may sometimes operate at cross purposes such that it is not possible to simultaneously optimize all of the biologically relevant physical properties of the membrane lipid bilayer.
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PMID:The biosynthetic incorporation of short-chain linear saturated fatty acids by Acholeplasma laidlawii B may suppress cell growth by perturbing membrane lipid polar headgroup distribution. 1209 84

Triacylglycerols (TAG) are fatty acid triesters of glycerol; there are diverse types of TAG with different properties depending on their fatty acid composition. The occurrence of TAG as reserve compounds is widespread among eukaryotic organisms such as yeast, fungi, plants and animals, whereas occurrence of TAG in bacteria has only rarely been described. However, accumulation of TAG seems to be widespread among bacteria belonging to the actinomycetes group, such as species of Mycobacterium, Streptomyces, Rhodococcus and Nocardia. Fatty acids in acylglycerols in cells of Rhodococcus opacus PD630 accounted for up to 87% of the cellular dry weight. TAG biosynthesis, justifying an oleaginous status, seems to be restricted mainly to this group of bacteria, but occurs to a minor extent also in a few other bacteria. The compositions and structures of bacterial TAG vary considerably depending on the microorganism and on the carbon source, and unusual acyl moieties, such as phenyldecanoic acid and 4,8,12 trimethyl tridecanoic acid, are also included. The principal function of bacterial TAG seems to be as a reserve compound. Other functions that have been discussed include regulation of cellular membrane fluidity by keeping unusual fatty acids away from membrane phospholipids, or acting as a sink for reducing equivalents. In recent years, basic aspects of the physiology and biochemistry of bacterial TAG accumulation, and the molecular biology of the lipid inclusion bodies have been reported. TAG are used for nutritional, therapeutic and pharmaceutical purposes and serve as a source of oleochemicals.
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PMID:Triacylglycerols in prokaryotic microorganisms. 1246 75

A phytochemical investigation in plantlets of the Brazilian medicinal tree Virola surinamensis resulted in the isolation and structural determination of four new compounds: 3-hydroxy-4-methyl-2-(11'-piperonyl-n-undecyl)-butenolide; 3-hydroxy-4-methyl-2-(7'-piperonyl-n-heptyl)-butanolide; 9'-(3,4-methylenedioxy-phenyl)-nonanoic acid and 13'-(3,4-methylene-dioxyphenyl)-tridecanoic acid. Thirteen compounds previously isolated from seeds and adult plants were also reported.
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PMID:New butenolides in plantlets of Virola surinamensis (Myristicaceae). 1546 49

This is the first evidence of a naturally bound fatty acid to a group I Phospholipase A(2) (PLA(2)) and also to a PLA(2) with Asp 49. The fatty acid identified as n-tridecanoic acid is observed at the substrate recognition site of PLA(2) hydrophobic channel. The complex was isolated from the venom of Bungarus caeruleus (Common Indian Krait). The primary sequence of the PLA(2) was determined using the cDNA method. Three-dimensional structure has been solved by the molecular replacement method and refined using the CNS package to a final R factor of 19.8% for the data in the resolution range from 20.0 to 2.7 A. The final refined model is comprised of 912 protein atoms, one sodium ion, one molecule of n-tridecanoic acid, and 60 water molecules. The sodium ion is located in the calcium-binding loop with a sevenfold coordination. A characteristic extra electron density was observed in the hydrophobic channel of the enzyme, into which a molecule of n-tridecanoic acid was clearly fitted. The MALDI-TOF measurements of the crystals had earlier indicated an increase in the molecular mass of PLA(2) by 212 Da over the native PLA(2). A major part of the ligand fits well in the binding pocket and interacts directly with His 48 and Asp 49. Although the overall structure of PLA(2) in the present complex is similar to the native structure reported earlier, it differs significantly in the folding of its calcium-binding loop.
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PMID:Crystal structure of the complex formed between a group I phospholipase A2 and a naturally occurring fatty acid at 2.7 A resolution. 1565 72

The crystal structures of synthetic unsymmetrical 1-glucosamide- and 1-galactosamide bolaamphiphiles, 13-[(beta-d-glucopyranosyl)carbamoyl]tridecanoic acid (1) and 15-[(beta-d-galactopyranosyl)carbamoyl]pentadecanoic acid (2), respectively, were elucidated by single-crystal X-ray analysis. The space group for 1 is P2(1), Z=2 with cell dimensions: a=8.6816(9), b=4.8578(5), c=26.250(3)A, beta=91.460(2) degrees ; that for 2P2(1), Z=2 with cell dimensions: a=4.90(1), b=40.139(1), 6.289(1)A, beta=106.48(1) degrees . The glucopyranosyl and galactopyranosyl rings in 1 and 2, respectively, take a (4)C(1) chair conformation. In the crystal lattice, the 1-glucosamide 1 forms a symmetrical monolayer lipid membrane (MLM) structure in which the molecules are packed in an antiparallel fashion, while 1-galactosamide 2 has an unsymmetrical MLM with parallel molecular packing. The stereochemistry of the sugar hydroxy group proved to affect their hydrogen-bonding networks and induce the polymorphism of the MLM.
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PMID:Polymorphism of monolayer lipid membrane structures made from unsymmetrical bolaamphiphiles. 1616 72

Infrared external reflection (IER) spectra of sodium dodecyl sulfate (SDS) monolayers at the air-solution interface and infrared transmission spectra of the corresponding aqueous solutions were measured at various SDS concentrations and temperatures. A comparison between the spectra of adsorbed monolayers and bulk solutions revealed that the conformational order of the SDS alkyl-chain at the air-solution interface improved with increasing the SDS concentrations, up until the saturation adsorption, and that the conformational order of the adsorbed SDS monolayer was higher than those of monomers and micelles. In addition, below the Krafft point temperature, the adsorbed SDS was maintained in the liquid crystal state, while SDS in the bulk solution was in the crystalline state. Furthermore, the SDS adsorption density was evaluated based on the IER band intensities of the insoluble monolayer of tridecanoic acid with an identical alkyl chain length to SDS.
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PMID:Effects of concentration and temperature on SDS monolayers at the air-solution interface studied by infrared external reflection spectroscopy. 1685 24

The monolayer characteristics of two very similar amphiphiles, N-tridecyl-beta-hydroxypropionic acid amide (C13H27-NH-CO-C2H4OH; THPA) and N-(beta-hydroxyethyl)tridecanoic acid amide (C13H27-CO-NH-C2H4OH; HETA), the chemical structure of which is only changed by exchanging the position of the two substituents at the acid amide group, are compared. These small changes in the chemical structure give rise to large differences in the phase behavior of the HETA and THPA monolayers, as concluded from the differences in the surface pressure-area (pi-A) isotherms. Since both amphiphiles have the same alkyl chain length, the shift of the fluid/condensed phase transition pressure pi(c) to higher temperatures from THPA to HETA indicates a stronger polar character of the THPA headgroup. Considerable differences between the HETA and THPA monolayers also exist in the domain morphology, although, in both cases, six arms usually grow from a round center. The fractal-shaped HETA domains grow by tip splitting under the formation of numerous doubloons so that branching is considerably limited. This suggests a certain fluidity of the HETA condensed phase. The main differences of the domains result from the higher crystallinity. The starlike THPA domains have dendritic character and can form curved dendrites, which are partially two-dimensional twins due to the formation of dislocations in the two-dimensional lattice structure. In the case of HETA monolayers, the grazing incidence X-ray diffraction studies reveal a hexagonal packing of the alkyl chains oriented perpendicularly to the surface in an LS phase. In the case of THPA monolayers, an oblique lattice is formed. However, at low temperatures, a second phase transition between two condensed phases occurs that is demonstrated by an abrupt transition between two different oblique lattice structures at the surface pressure where a cusp in the pi-A isotherms occurs at T < 10 degrees C.
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PMID:Effect of the exchange of substituent position in an amide amphiphile on the monolayer characteristics. 1686 99

Crystal structures of the high-temperature phases of odd-numbered fatty acids (C(n)H(2n-1)OOH) from tridecanoic acid (C(13)H(25)OOH) to tricosanoic acid (C(23)H(45)OOH) are presented in this article. They have been determined from high-quality X-ray powder-diffraction patterns. Two types of high-temperature phases are adopted: one monoclinic A2/a with Z=8 for the fatty acids with n=13 and n=15, denoted as C'', and one monoclinic P2(1)/a with Z=4 for the longer-chain fatty acids, denoted as C'. It appears that the packing arrangement of the alkyl chains and of the carboxyl groups is similar in all of the structures. However, the arrangement at the methyl-group interface differs between the C' and C'' forms. A survey of the intermolecular interactions involved in these polymorphs coupled with a study of the effects of temperature on the structures have led us to a better understanding of the arrangement of the molecules within the high-temperature solid phases of odd-numbered fatty acids.
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PMID:Structures of the high-temperature solid phases of the odd-numbered fatty acids from tridecanoic acid to tricosanoic acid. 1721 66

The monolayer features of two very similar amphiphiles, N-tridecyl-beta-hydroxypropionic acid amide (THPA) and N-(beta-hydroxyethyl) tridecanoic acid amide (HETA) and their 1:1 mixture are studied. The behavior of the mixed monolayer is of special interest as already the pure components reveal large differences of the surface pressure-area (pi-A) isotherms, in particular, because of the second phase transition between two condensed phases at low temperatures in the THPA monolayer. This second phase transition occurs in the mixed monolayer, as well. The thermodynamic characteristics of the mixed HETA/THPA monolayers are compared with those of the pure components. The thermodynamic analysis is performed on the basis of the equations of state for the monolayer in the fluid (G, LE)/condensed (LC) transition region (A<Ac) with bimodal distribution (large clusters and monomers) and in the fluid (G, LE) state (A>or=Ac) considering the contribution of the entropy nonideality, caused by the mixing of monomers and clusters. Good agreement between the experimental pi- A isotherms and the theoretical results are obtained. The results of the thermodynamic analysis allow conclusions on the specific phase properties of the mixed HETA/THPA monolayers. Finally the additive model applied for the theoretical description at higher temperatures provides good agreement with the experimental results at temperatures of >or=20 degrees C.
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PMID:Thermodynamic characterization of mixed monolayers of two similar amide amphiphiles different only by exchange of substituents position. 1868 70

Nitrate-reducing enrichments, amended with n-hexadecane, were established with petroleum-contaminated sediment from Onondaga Lake. Cultures were serially diluted to yield a sediment-free consortium. Clone libraries and denaturing gradient gel electrophoresis analysis of 16S rRNA gene community PCR products indicated the presence of uncultured alpha- and betaproteobacteria similar to those detected in contaminated, denitrifying environments. Cultures were incubated with H(34)-hexadecane, fully deuterated hexadecane (d(34)-hexadecane), or H(34)-hexadecane and NaH(13)CO(3). Gas chromatography-mass spectrometry analysis of silylated metabolites resulted in the identification of [H(29)]pentadecanoic acid, [H(25)]tridecanoic acid, [1-(13)C]pentadecanoic acid, [3-(13)C]heptadecanoic acid, [3-(13)C]10-methylheptadecanoic acid, and d(27)-pentadecanoic, d(25)-, and d(2)(4)-tridecanoic acids. The identification of these metabolites suggests a carbon addition at the C-3 position of hexadecane, with subsequent beta-oxidation and transformation reactions (chain elongation and C-10 methylation) that predominantly produce fatty acids with odd numbers of carbons. Mineralization of [1-(14)C]hexadecane was demonstrated based on the recovery of (14)CO(2) in active cultures.
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PMID:Anaerobic biodegradation of n-hexadecane by a nitrate-reducing consortium. 1911 7


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