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Chemistry.

SYNTHESIS OF 4-AMINO DERIVATIVES OF 5,7-DICHLOROKINURENIC ACID THAT LED TO UNEXPECTED PRODUCTS VIA DETOSYLATION. Stephen Craig, Al Nichols, and Nagarajan Vasumathi, Dept. of Physical and Earth Sciences, Jacksonville State Univ., Jacksonville, AL 36265.

Starting with ethyl 5,7-dichloro-4-{[(4-methylphenyl)sulfonyl]amino}quinoline-2-carboxylate prepared by a previously reported method (Nichols and Yielding, 1993), a reaction was conducted using triphosgene and glycine to produce the corresponding tosyl derivative of [({[5,7-dicholor-2-(ethoxycarbonyl)quinolin-4-yl]amino}carbonyl)amino]acetic acid. It was anticipated that the tosyl group would then be removed by acid hydrolysis. Elemental analysis of a product isolated from this reaction revealed that the tosyl group was no longer a part of the quinoline ring compound. This detosylation had not been observed in previous studies (Nichols and Yielding, 1998). When this product was reacted with anhydrous ethyl alcohol in the presence of thionyl chloride, a product was obtained that was identified by proton NMR and elemental analysis as ethyl 5,7-dichloro-4-[(ethoxycarbonyl)amino]quinoline-2-carboxylate. The formation of a 4-amino isocyanate intermediate could explain these results.

INVESTIGATING THE ACTIVITIES OF [beta]-GLUCOSIDASE AND INSULIN POTENTIATING FACTOR (IPF) IN BITTER GOURD (Momordica charantia) PROTEINS. Mijitaba Hamissou, Amanda Henderson, and Nagarajan Vasumathi. Jacksonville State University, Jacksonville, AL 36265

Plant products have always been important tools in drug discovery. Drug discovery usually requires a thorough investigation of biologically active compounds produced by the plant. [beta]-glucosidase (3.2.1.21), an enzyme that hydrolyzes [beta]-glycosidic bonds between the reducing side of glucose and an alkyl aglycone or oligosaccharide is a powerful tool used in drug discovery. Plant [beta]-glucosidases belong to glycosyl hydrolase family and play important roles in defense, phytochrome regulation, oligosaccharide catabolism. Because of their involvement in deactivation or storage of some endogenous bioactive substances, [beta]-glucosidases are used as indicators of drug-related activities in plant extracts. Bitter gourd, Momordica charantia, a common vegetable cultivated in India, is used as a folk medicine for treatment of many ailments including diabetes. Our objectives are to search for drug-related activities in bitter gourd extracts by investigating an insulin potentiating factor (IPF) and [beta]-glucosidase activity. Bitter gourds were purchased from the International Market in Georgia, divided into mesocarp and seeds. Each portion was homogenized in N[a.sub.3]P[O.sub.4] buffer and native enzymes were harvested by centrifugation. [beta]-glucosidase activities were studied biochemically and IPF was investigated by western blot analysis against an anti-insulin antibody. Preliminary data indicated the presence of one of [beta]-glucosidase substrates and a weak cross reactivity to anti-insulin antibody. Lipids were obtained from the seed portion and analyzed by TLC. Early lipid analyses indicated a possible presence the omega fatty acid linolenic acid that may play a role in the bioactive properties of the seed extract.

INVESTIGATING UPTAKE OF MERCURY FROM CONTAMINATED SOIL BY DECIDUOUS TREES IN CALHOUN COUNTY, ALABAMA. B. Driggers, J. Kent, C. Loveless, E. Pentecost, L. Pentecost, D. Steffy, and A. Nichols, Dept. of Physical and Earth Sciences, Jacksonville St. Univ., Ala., 36265.

Mercury contaminated landfill material has been used to landscape a city park and a nearby shopping mall, both of which are adjacent to Snow Creek in southern Calhoun County. An ongoing investigation of mercury occurrence in this watershed has found that the mercury from the fill material has been redistributing across the fluvial deposition system and has been bioaccumulating in various trophic levels of the freshwater ecosystem. This investigation extends the study to include the measurement of mercury uptake by Green Ash (Fraxinus pennsylvanica), a deciduous tree occurring in the contaminated flood plain deposits, which have an average measured value of 0.56 mg/Kg. Based on 9 samples of each section of 3 different trees located in the same area, the root tissue consistently has the highest value (0.0134 mg/Kg), the trunk tissue has the next highest (0.0058 mg/Kg), and the twigs of the trees has the lowest values (0.0017 mg/Kg).

VALIDATION OF ALABAMA WATER WATCH TEST METHODS FOR TURBIDITY AND pH VIA COMPARISON OF PAIRED TEST KIT AND METER DATA. Michael William Mullen, Department of Environmental and Biological Sciences, Troy University, Troy, AL 36082.

State water quality management agencies seldom have the resources needed to monitor more than a small percentage of water bodies. The Alabama Water Watch Program has selected and obtained USEPA approval for monitoring methods used by citizen volunteers for water quality monitoring. While these methods do not provide the precision of research or agency protocols for water monitoring, they can provide useful trend data that would otherwise be unavailable. This paper examines the performance of volunteer methods for pH and turbidity by comparing volunteer data with meter data. Data obtained using the visual turbidity tube (LaMotte Company) used by volunteers was compared with data from a USEPA approved turbidimeter (LaMotte 2020 Turbidimeter). Data obtained from a visual wide-range colorimetric pH comparator (LaMotte Company) used by volunteers was compared with data obtained using pocket pH meters (YSI Model 10). Volunteer methods wee found to compare favorably with the meter methods similar to those that might be employed by water management agencies.

EVALUATIONS OF CELLULOSE SUPPORTED PALLADIUM CATALYST Fatima Carmichael, Scott Brown, Kevin H Shaughnessy, Department of Chemistry and Center for Green Manufacturing, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336

Palladium catalysts are widely utilized in coupling reactions such as Suzuki coupling. These reactions are becoming more commonly used in the synthesis of fine chemicals. For fine chemical synthesis it is desirable to have a catalyst that can be easily separated from the product stream. The focus of this research has been to use cellulose supported palladium catalyst and a sterically demanding phosphine ligand to promote cross-coupling reactions. Phosphine ligands promote reactivity of aryl halide substrates with boronic acid to generate biphenyl moities. Cellulose is a renewable resource and it is compatible with aqueous solvent systems. It is also highly functionalized, which may stabilize the heterogeneous palladium catalyst. By evaluating cellulose supported reactions verses carbon supported reactions we hope to be able to find more efficient and sustainable heterogeneous catalyst for cross-coupling reactions.
 EQUILIBRIUM CONSTANT CALCULATOR FOR CHEMICAL REACTIONS AT HIGH
 TEMPERATURES, E. B. Garner, and M. B. Moeller, Dept. of
 Chemistry and Industrial Hygiene, Univ. of North Alabama,
 Florence, AL 35632.

 The National Institute of Standards and Technology (NIST)
 Chemistry WebBook contains thermochemical data on over 7000
 organic and small inorganic compounds. An Excel workbook,
 K-equilibrium Calculator, has been constructed to facilitate
 the use of the NIST data for calculating values of equilibrium
 constants for chemical reactions from 298K to temperatures up
 to 6000K. The project objective was to create a calculator that
 would be easy to use, transportable, readily understood, easily
 modified, and accurate. Occasional small gaps in the NIST
 WebBook heat capacity values have been filled using a simple
 algorithm. Gibbs free energy values calculated with
 K-equilibrium Calculator agree well with values calculated from
 Free Energy Function tables. The workbook Calculator can be
 downloaded at www2.una.edu/mmoeller.


CHEMISTRY OF GLUCOSINOLATES: EXTRACTION AND CHARACTERIZATION

Tahirah Farrer-Bradle[y.sup.1] N. Paul Nole[n.sup.2], Bernadette Earl[y.sup.3], Ayesha J. Mindingal[l.sup.4], Monica Frazie[r.sup.4], Pamela M. Leggett-Robinso[n.sup.*1] [.sup.1]Department of Chemistry, Tuskegee University, [.sup.2]Department of Animal Science, Tuskegee University; [.sup.3]Department of Biology, Tuskegee University; [.sup.4]CBR/RCMI, Tuskegee University

Diets rich in cruciferous vegetables such as broccoli, cabbage, brussel sprouts, bok choy, and cauliflower, have been shown to lower the risks of one developing several cancers such as lung, pancreatic, breast and prostate cancer[.sup.1-3] This decrease in cancer development has been attributed to a constituent of cruciferous vegetables, isothiocyanate, a derivative from the family of glucosinolates[.sup.3,4] Previous data show that the specific effects of a particular ITC on the metabolism of a given carcinogen must be determined independently as they vary from one carcinogen to another[.sup.2,5] Moreover, the effects of ITCs are dependent on the methods used to isolate the extracts, the specific carcinogen studied, and the target tissue involved[.sup.4] Methodology for analysis have not been uniformly applied and the actual chemistry of glucosinolates remains under investigation. Here we present data on the various methods for isolating ITCs from broccoli, cabbage, and bok choy as well as the proliferative effects of the isolated ITCs on prostate (PC-3) cancer cells.

SYNTHESIS AND STRUCTURAL DETERMINATION OF UREA FORMALDEHYDE CONDENSATION PRODUCTS Ryan J. Johnson, Thomas P. Murray and Jason P. Weisenseel, Dept. of Chemistry & Industrial Hygiene, Univ. of N. Ala., Florence, AL 35632

Many controlled-release nitrogen (N) fertilizers contain urea formaldehyde condensation products as their active ingredient. Fast acting N fertilizers commonly contain urea or ammonia that is digested by ammonia-oxidizing bacteria (AOB) in the soil to form nitrates. Nitrification of urea and ammonia by AOB is relatively fast and the digestion rate has been studied and is well understood. Urea formaldehyde condensation product nitrification by AOB is very slow resulting in the controlled release of nitrates. The kinetics of this enzymatic digestion has not been studied in detail and the slow rate of nitrification is poorly understood. Two urea formaldehyde condensation products, methylene diurea (MDU) and dimethylene triurea (DMTU), have been synthesized and characterized by NMR spectroscopy. The NMR data was used to model the three-dimensional structure of these compounds. The ultimate goal of this project is to measure the enzymatic digestion rates of these compounds and use the three-dimensional structures to rationalize the slow digestion rates.

HYMENOMYCETES (FUNGI) FROM THE MOBILE BAY AREA. Juan L. Mata, Dept. of Biological Sciences, Univ. of South Alabama, Mobile, AL. 36688

A survey of the fleshy fungi from the Mobile Bay and vicinities was started last year. A reason motivating this process was that the only published work on the mycoflora of Alabama dates back to 1905, with most of the collection records coming from Lee County and vicinities. Ongoing fungal forays in southern Alabama and vicinities allow us to document taxa previously reported but also increase our capacity for thorough revision of their taxonomic and systematic status. In the long term, a current list of reported macrofungal species will be generated, all of which will be backed by specimens deposited in a herbarium. Here, a progress report of such work is given.

STUDY ON THE EFFECTS OF 18-CROWN-6 IN SOLID PHASE PEPTIDE SYNTHESIS. James T. Merrill and Lesli K. Bordas, Dept. of Chemistry & Physics, Spring Hill College, Mobile, AL 36608.

Since its initial development in 1963, side reactions and incomplete couplings have plagued synthetic peptide synthesis. It is well known that intermolecular interactions between the growing peptidyl backbone and neighboring peptide chains cause the formation of "aggregates" and low coupling yields. This research introduces the use of crown ethers to shield the growing chains from such unwanted interactions. The crown ethers provide intramolecular bonding thereby disrupting secondary structure formation in the growing peptide chains. Progress in this type of chemistry will eventually help pharmaceutical companies produce large, hard to isolate proteins and enzymes that may be used as treatments or possibly even cures to many diseases.

DETERMINATION OF TOTAL MERCURY IN FRESHWATER MUSSEL TISSUE FROM THE TENNESSEE RIVER IN NORTHWEST ALABAMA, Nathan C. Thacker, Amanda W. Davis, and Jason P. Weisenseel, Dept. of Chemistry & Industrial Hygiene, Univ. of N. Ala., Florence, AL 35632

Since the discovery that mercury from industrial pollution was the cause of Minamata disease in Japan, mercury contamination in aquatic systems is a major human health concern. Mercury contamination in the Tennessee River of Northwest Alabama is of special concern since a major discharge of mercury from a chlor-alkali facility into Pickwick Lake occurred in the 1960's. Additionally, one of the few remaining chlor-alkali facilities in the United States is still operating in Northwest Alabama, as well as a coal burning steam plant on the banks of the river in Colbert County. Both of these operations are known to generate mercury vapor in the atmosphere that is believed to accumulate in the aquatic ecosystem. Mussels are good biological indicators of the health of aquatic ecosystems. In this study, the total mercury concentration in the tissue of mussels collected in this region is being determined by atomic absorption spectroscopy. Preliminary data indicates the presence of mercury in the mussel tissue. The ultimate goal of this project is to determine the mercury content in the mussel tissues and shells to provide a timeline and geographic distribution of mercury in the river system.
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Publication:Journal of the Alabama Academy of Science
Date:Apr 1, 2006
Words:2082
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