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At least 163 records · Page 9Linked to original sources
PubMed2001

Polymer versus monomer as displacer in immobilized metal affinity chromatography.

Successful immobilized metal affinity chromatography (IMAC) of proteins on Cu2+-iminodiacetic acid Sepharose has been carried out in a displacement mode using a synthetic copolymer of vinyl imidazole and vinyl caprolactam [poly(VI-VCL)] as a displacer. Vinyl caprolactam renders the co-polymer with the thermosensitivity, e.g., property of the co-polymer to precipitate nearly quantitatively from aqueous solution on increase of the temperature to 48 degrees C. A thermostable lactate dehydrogenase from the thermophilic bacterium Bacillus stearothermophilus modified with a (His)6-tag [(His)6-LDH] has been purified using an IMAC column. For the first time it was clearly demonstrated that a polymeric displacer [poly(VI-VCL)] was more efficient compared to a monomeric displacer (imidazole) of the same chemical nature, probably due to the multipoint interaction of imidazole groups within the same macromolecule with one Cu2+ ion. Complete elution of bound (His)6-LDH has been achieved at 3.7 mM concentration of imidazole units of the co-polymer (5 mg/ml), while this concentration of free imidazole was sufficient to elute only weakly bound proteins. Complete elution of (His)6-LDH by the free imidazole was achieved only at concentrations as high as 160 mM. Thus, it was clearly demonstrated, that the efficiency of low-molecular-mass displacer could be improved significantly by converting it into a polymeric displacer having interacting groups of the same chemical nature.

Chromatography, Affinity↗
PubMed2005

Continuous spinning of a single-walled carbon nanotube-nylon composite fiber.

We report a chemical processing technology that allows the continuous spinning of single-walled carbon nanotubes (SWNTs)-nylon 6 (PA6) fibers by the in-situ polymerization of caprolactam in the presence of SWNTs, which simultaneously optimizes the morphology of the composite. We show that caprolactam is an excellent solvent for carboxylic-acid-functionalized SWNTs (SWNT-COOH) and that this allows the efficient dispersal of the SWNTs and subsequent grafting of PA6 chains to the SWNTs through condensation reactions between the carboxylic-acid group on SWNT-COOH and the terminal amine group of PA6. The existence of a graft copolymer between the PA6 chains and the SWNTs is demonstrated by IR, TGA, and AFM studies, and we show that the solubility of the polymerized material in formic acid is controlled by the degree of graft copolymerization. The amount of grafted PA6 chains that are attached to the SWNTs can be adjusted by controlling the concentration of the initiator (6-aminocaproic acid). The process leads to a uniform dispersion of the SWNTs, and the presence of the graft copolymer increases the polymer/SWNT compatibility while strengthening the interfacial interaction between the nanotube and matrix. The Young's modulus, tensile strength, and thermal stability of the SWNT-reinforced composite fibers produced by this process are significantly improved.

Journal Article↗
PubMed2005

Hierarchically structured monolithic silicalite-1 consisting of crystallized nanoparticles and its performance in the Beckmann rearrangement of cyclohexanone oxime.

In this study, we present a synthetic pathway for the fabrication of self-supporting zeolite monoliths consisting of crystallized nanoparticles. A resorcinol-formaldehyde-based organic aerogel is used as a template, and silicalite-1 is used as the zeolite example. The silicalite-1 monoliths obtained consist of individual well-defined zeolite nanocrystals with sizes of 30-40 nm. The monoliths exhibit a high mechanical stability and have hierarchical porosity, with micropores within the zeolite particles, a mesopore system formed by the packing of the nanoparticles, and a macropore system on the monolith level. Such monolithic zeolites show high selectivity typically above 80% to epsilon-caprolactam combined with a high rate of reaction of 0.46 g(caprolactame)/(g(catalyst).h) in the Beckmann rearrangement of cyclohexanone oxime.

Carbon↗
PubMed2000

Aqueous polymer two-phase systems formed by new thermoseparating polymers.

A set of new polymers that can be used as phase forming components in aqueous two-phase systems is presented. All polymers studied have thermoseparating properties i.e. form one separate polymer enriched phase and one aqueous solution when heated above the critical temperature. This property makes the polymers attractive alternatives to the polymers used in traditional aqueous two-phase systems such as poly(ethylene glycol) (PEG) and dextran. The thermal phase separation simplifies recycling of the polymers, thus making the aqueous two-phase systems more cost efficient and suitable for use in large scale. Thermoseparating polymers studied have been copolymers of ethylene oxide and propylene oxide (EO-PO), poly (N-isopropylacrylamide) (poly-NIPAM), poly vinyl caprolactam (poly-VCL) and copolymers of N-isopropylacrylamide and vinyl caprolactam with vinyl imidazole (poly(NIPAM-VI) and poly(VCL-VI), respectively). In addition, the copolymer poly(NIPAM-VI) has the property to be uncharged at pH above 7.0 and positively charged at lower pH. This allows the partitioning of protein to be directed by changing the pH in the system instead of the traditional addition of salt to direct the partitioning. Hydrophobically modified EO-PO copolymer (HM-(EO-PO)) with alkyl groups (C14) at both ends forms two-phase system with for example poly(NIPAM-VI). The phase diagram for poly(NIPAM-VI)/HM-(EO-PO) was determined and the model proteins lysozyme and BSA were partitioned in this system. For BSA in poly(NIPAM-VI)/HM-(EO-PO) system a change in pH from 8.0 to 5.4 results in a change of partition coefficient from K = 0.8 to K = 5.1, i.e. BSA could be transferred from the HM-(EO-PO) phase to the poly(NIPAM-VI) phase. BSA partitioning in poly(NIPAM-VI)/HM-(EO-PO) system allows quantitative BSA recovery, and recoveries of poly(NIPAM-VI) and HM-(EO-PO) were 53% and 92%, respectively, after the thermoseparation step.

Animals↗
PubMed1988

The initiator tRNA acceptance assay as a short-term test for carcinogens. 2. Results with ten compounds selected by the International Programme on Chemical Safety for the evaluation of short-term tests for carcinogens.

Eight carcinogenic and two non-carcinogenic compounds that are difficult to detect by short-term tests (acrylonitrile, benzene, benzoin, caprolactam, diethylhexylphtalate, diethylstilbestrol, hexamethylphosphoramide, phenobarbital, safrole and o-toluidine) were tested independently in Prague and in Heidelberg by the newly developed initiator tRNA acceptance assay. Seven out of eight tested carcinogens gave a positive response in this assay, only safrole showed a false negativity in both laboratories. Both non-carcinogenic compounds, benzoin and caprolactam, exhibited no activity. An absolute qualitative agreement was found with all compounds tested between the results of both laboratories. With the exception only of phenobarbital (intermediate activity in Prague and low in Heidelberg) the quantitative results obtained in both laboratories were comparable. The initiator tRNA acceptance assay thus appears to be a reliable short-term test for carcinogenicity with good reproducibility.

Carcinogens↗
PubMed1990

Synthesis, central nervous system activity and teratogenicity of a homothalidomide.

The optical isomers of alpha-phthalimidoadipinimide (1) were synthesized by a route based on D(+)- and L(-)-amino-epsilon-caprolactam (5) as synthon. The isomers of 1 were obtained in high yields by treating D(+)- and L(-)-amino-epsilon-caprolactam (5) with N-carboethoxyphthalimide (4), followed by oxidation with benzeneseleninic anhydride (7). The teratogenic potency of both isomers of 1 was studied by the HET-(Hen's Egg Test); 1 caused distinctly lower teratogenic effects in contrast to thalidomide (2). D(-)-1 and L(+)-1 showed sedative effects with a lower activity than 2. Both are more stable in alkaline solution at the same time with a smaller tendency for racemization.

Animals↗
PubMedDate not supplied

Stabilization of proteases by entrapment in a new composite hydrogel.

A new one-step procedure for entrapping proteases into a polymeric composite calcium alginate-poly(N-vinyl caprolactam) hydrogel was developed that provided 75-90% retention of the activity of entrapped enzymes compared to soluble ones. Properties of entrapped carboxypeptidase B, trypsin, and thrombin were investigated. The immobilized enzymes were active within a wide pH range. The temperature optima of entrapped trypsin and carboxypeptidase B were approx 25 degrees C higher than that of the soluble enzymes, and the resistance to heating was also increased. The effects of various polar and nonpolar organic solvents on the entrapped proteases were investigated. The immobilized enzymes retained their activity within a wide concentration range (up to 90%) of organic solvents. Gel-entrapped trypsin and carboxypeptidase (CPB) were successfully used for obtaining human insulin from recombinant proinsulin. The developed stabilization method can be used to catalyze various reactions proceeding within wide pH and temperature ranges.

Alginates↗
PubMed2006

Biodegradation of synthetic polymers by composting and fungal treatment.

Two types of copolymers--poly(ester-amide)s--by the anionic copolymerization of epsilon-caprolactam and epsilon-caprolactone, and aromatic-aliphatic copolyesters based on glycolyzed polyethylene terephthalate from used beverage bottles and epsilon-caprolactone were prepared. Biodegradation tests of these copolymers were performed by two methods, viz. composting under controlled conditions and treatment with ligninolytic fungi. Both methods resulted in degradation of the copolymers, composting being more robust. Out of fungal strains tested Inonotus hispidus degraded aromatic-aliphatic copolyesters most intensively.

Basidiomycota↗
PubMed1989

Evaluation of chromosomal aberrations in bone marrow of 1C3F1 mice.

The chemical caprolactam (CAP) was tested for induction of chromosomal aberrations in bone marrow of male and female 1C3F1 mice at a single dose of 1000 mg/kg by oral intubation of an aqueous solution at a volume of 0.1 ml/10 g of body weight. Bone marrow was sampled from groups of 10 animals 24, 30 and 48 h after treatment. CAP did not produce chromosomal aberrations under the present experimental conditions. At the same time, benzo[a]pyrene, used as a positive control, significantly increased the aberration rates at a dose of 63 mg/kg.

Animals↗
PubMed2004

The formation of poly(ester-urea) networks in the absence of isocyanate monomers.

The polymerization of N,N' carbonylbis (caprolactam) (CBC) and polyol in the presence of alcoholate as catalyst produced cross-linked poly(ester-urea)s via ring opening addition reaction. In contrast to conventional synthetic routes, the use of non-toxic CBC eliminates the need for toxic isocyanate-based monomers. The structure of the molecules resulting from model reactions was confirmed using FT-IR and (1)H- and (13)C-NMR spectroscopy. Poly(ester-urea) networks exhibit rubber-like mechanical properties and high-temperature stability. Cell adhesion and cell growth on the polymers evidenced the high biocompatibility of the material. Degradation of the poly(ester-urea)s was investigated at 70 degrees C in neutral and basic aqueous solution. The degradation depends on the swelling behavior of the samples. Mechanical properties, good biocompatibility, and degradation behavior of the CBC/polyol-based polymers make them interesting materials for biomedical applications.

Absorbable Implants↗
PubMed2003

Deoligomerization: a new route to lactams from unsaturated amides via radical oligomerization.

[reaction: see text] Triethylborane-initiated atom transfer radical oligomerization of N-allyl or N-(3-butenyl)iodoacetamides followed by treatment with hydrochloric acid and subsequent neutralization with K(2)CO(3) led to the formation of the corresponding 5-hydroxyl-substituted delta-lactams or caprolactams, respectively. This oligomerization-deoligomerization sequence serves as an alternative to the corresponding intramolecular cyclization reactions.

Amides↗
PubMed2004

Molecular mechanism of dielectrically controlled optical resolution (DCR).

We have recently found the first example of dielectrically controlled optical resolution (DCR). By adjusting the dielectric constant of the solvent used in the resolution process, each optical isomer of (R,S)-alpha-amino-epsilon-caprolactam can be selectively obtained using N-tosyl-(S)-phenylalanine as a chiral selector. The molecular mechanism of DCR has been investigated by comparing the molecular and crystal structures of the optical selector, its target substrate and their diastereomeric salts. Strong hydrophobic interactions between the phenyl rings of the optical selector govern the molecular aggregation of the selectors and form a hydrophilic layer in which molecular recognition takes place. The recognition site in the hydrophilic layer can inherently identify both of the isomers. The dielectric constant of the solvent used in the discrimination process controls the intermolecular interaction which determines the isomer to be selected. The molecular mechanism of DCR disclosed in this study strongly suggests that DCR is not a specific but a general phenomenon. This method can be applicable to a large variety of optical resolution processes.

Caprolactam↗
PubMed2004

Hyper-inducible expression system for streptomycetes.

Streptomycetes produce useful enzymes and a wide variety of secondary metabolites with potent biological activities (e.g., antibiotics, immunosuppressors, pesticides, etc.). Despite their importance in the pharmaceutical and agrochemical fields, there have been no reports for practical expression systems in streptomycetes. Here, we developed a "P(nitA)-NitR" system for regulatory gene expression in streptomycetes based on the expression mechanism of Rhodococcus rhodochrous J1 nitrilase, which is highly induced by an inexpensive and safe inducer, epsilon-caprolactam. Heterologous protein expression experiments demonstrated that the system allowed suppressed basal expression and hyper-inducible expression, yielding target protein levels of as high as approximately 40% of all soluble protein. Furthermore, the system functioned in important streptomycete strains. Thus, the P(nitA)-NitR system should be a powerful tool for improving the productivity of various useful products in streptomycetes.

Aminohydrolases↗
PubMedDate not supplied

Analysis of migrants from nylon 6 packaging films into boiling water.

Ultra-violet spectrophotometry (UV), high performance liquid chromatography (HPLC) and liquid chromatography coupled to mass spectroscopy (LC-MS) were used to identify and quantify oligomers extracted with boiling water from two different nylon 6 films used in boil-in-bag food packaging. The results indicated the loss of up to 1.5% of the original nylon film weight, into the boiling water, as caprolactam and cyclic oligomers up to the nonamer. Extraction time, thickness and type of film used, were found to be parameters which affected the levels of these migrants. These results will be relevant to situations in which food is cooked in the water used to heat the pouch contents.

Caprolactam↗
PubMed1976

Metabolism of N-nitrosohexamethyleneimine.

The metabolism of [2-14C]N-nitrosohexamethyleneimine in male MRC-Wistar rats was studied and some of the major urinary metabolites were identified. The extent of total oxidation to 14CO2 was 18.1% in 24 hours and radioactivity incorporation was observed in various tissues; that in the liver was the highest. Analysis of urine after 24 hours showed that 36.7% of the radioactivity administered was excreted by this route, with a minimum of 11 products present. Hexamethyleneimine (HX), epsilon-caprolactam, epsilon-aminocaproic acid, and 6-aminocaprohydroxamic acid were the identified metabolites. Of the remaining products, two appeared to result from HX metabolism and one was a glucuronide conjugate. No parent compound was found.

Aminocaproic Acid↗
PubMed2006

Acrylic acid removal by acrylic acid utilizing bacteria from acrylonitrile-butadiene-styrene resin manufactured wastewater treatment system.

The aim of this study is to isolate the acrylic acid utilizing bacteria from the ABS resin manufactured wastewater treatment system. The bacteria should have the ability to remove acrylic acid and tolerate the acrylonitrile and acrylamide toxicity. The aim is also to understand the performance of isolated pure strain for treating different initial acrylic acid concentrations from synthetic wastewater. The results are: twenty strains were isolated from the ABS resin manufactured wastewater treatment system and twelve of them could utilize 600 mg/l acrylic acid for growth. Seven of twelve strains could tolerate the acrylonitrile and acrylamide toxicity, when the concentration was below 300 mg/l. Bacillus thuringiensis was one of the seven strains and the optimum growth temperature was 32 degrees C. Bacillus thuringiensis could utilize acrylic acid for growth, when the initial acrylic acid concentration was below 1,690.4 mg/l. Besides this, when the initial acrylic acid concentration was below 606.8 mg/l, the acrylic acid removal efficiency exceeded 96.3%. Bacillus thuringiensis could tolerate 295.7 mg/l acrylamide and 198.4 mg/l acrylonitrile toxicity but could not tolerate 297.3 mg/l epsilon-caprolactam.

Acrylates↗