JSCS - Vol 65, No 2

JSCS Vol 65, No. 2

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J. Serb. Chem. Soc. 65 (2)81-86(2000)
UDC 547.854.3/.4:535.343
JSCS-2728
Original scientific paper

Effects of substituents on the electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils in different solvents. Part II.

N. VALENTIC, G. USCUMLIC and M. RADOJKOVIC-VELICKOVIC

Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P.O.Box 494, YU-11001 Belgrade, Yugoslavia

(Received 15 July, revised 8 October 1999)
Absorption spectra of some 3-N-(4-substituted phenyl)-5-carboxy uracils, previously determined in twelve solvents, are correlated with substituent s_p⁺ values or by dual substituent parameter correlations involving s_l and s_R⁺ values. The substituents at the phenyl nucleus are as follows: H, Cl, Br, I, Me, Et, OMe, COOH and NO₂. Considering the structure of the investigated system, it is very probable that the effect of the substituent at the phenyl nucleus on the electronic spectra of the substituted uracils is influenced by resonance interactions between the electron pairs of both the nitrogen atoms, the carbonyl groups and the substituent itself. The polarity of the reaction medium also affects the complex resonance interactions in the molecules of the investigated compounds. The obtained results support a suggestion made by Brownlee and Topsom that UV/visible spectral shifts can conform to reasonable precise linear free energy relationships if the substituent is not a part of the chromophoric system.
Keywords: absorption spectra, substituent effects, solvent effects, intramolecular hydrogen bond.

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J. Serb. Chem. Soc. 65(2)87-93(2000)
UDC 547-314: 547.473:542.9
JSCS-2729
Original scientific paper

The synthesis of some unsaturated 4-substituted-g-lactones

SUREN HUSINEC and VLADIMIR SAVIC*

Institute of Chemistry, Technology and Metallurgy, Center for Chemistry, Njegoseva 12, P.O.Box 815, YU-11000 Belgrade and
*Faculty of Pharmacy, Department of Organic Chemistry, Vojvode Stepe 450, YU-11000 Belgrade, Yugoslavia

(Received 16 July, revised 1 October 1999)
The synthesis of conjugated and nonconjugated unsaturated 4-substituted lactones of type 1 and 2 are described. The type 1 lactone was prepared by a two step procedure employing Bredereck's reagent. The type 2 lactone was synthesised by combining the Claisen-Ireland rearrangement and selenolactonisation.
Keywords: unsaturated lactones, synthesis.

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J. Serb. Chem. Soc. 65(2)95-102(2000)
UDC 547.863.11/547.587.51
JSCS-2730
Original scientific paper

Synthesis and biological activity of some heterocyclic compounds containing quinoxaline and coumarin moieties

I. M. EL-DEEN and M. E. ABD EL-FATTAH*

Faculty of Education, Suez Canal University, Port-Said, Egypt and
*Chemistry Department, Faculty of Science, Suez Canal University, Ismailia, Egypt

(Received 28 June 1999)
2,3-Dichloroquinoxaline (2) condensed with 7,8-dihydroxy-4-methylcoumarin to give the 1,4-dioxane derivative 4. 2.3-Dichloroquinoxaline (2) reacted with 4-hydroxycoumarin, 7-hydroxy-4-methylcoumarin and acyl hydrazide 13 to give either the 2,3-(dicoumarin-4-yloxy)quinoxaline (6) or the 2,3-di-(4-methylcoumarin-7-yloxy)quinoxaline (7) or the 2-chloro-3-(coumarin-4-yloxy)quinoxaline (8) or the 2-chloro-3-(4-methylcoumarin-7-yloxy) quinoxaline (9) or the ditriazoloquinoxaline 14 or the oxa-diazinoquinoxaline 16, depending on the relative ratios of the reactants and the reaction conditions.
Keywords: 2,3-dichloroquinoxaline, reaction with coumarin derivatives.

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J. Serb. Chem. Soc. 65(2)103-111(2000)
UDC 547-314:547.7281:542.913/57.083.1/
JSCS-2731
Original scientific paper

Microbiological transformation of a synthetic benzofurane type lactone

S. SUKDOLAK, S. SOLUJIC-SUKDOLAK and Lj. KRSTIC*

Department of Chemistry, University of Kragujevac, R. Domanovica 12, P.O.Box 60, YU-34000 Kragujevac, Yugoslavia and
*Institute for Chemistry, Technology and Metallurgy, Njegoseva 12, YU-11000 Belgrade, Yugoslavia

(Received 22 February 1999)
The aim of this work was the investigation of the biotransformation ability of a synthetic benzofurane type g-lactone. This work was based on the microbiological reactions of Aspergillus niger, Saccharomyces cerevisiae, Bacillus mycoides, Agrobacterium tumefaciens, Pseudomonas glicinea and Pseudomonas fluorescens to obtain new active derivatives. Four biotransformation products were determined. The lactone was used for two purposes, as an additive for the nutrient substrate and as a source of organic carbon.
Keywords: synthesis, g-lactone, biotransformation, d-lactone.

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J. Serb. Chem. Soc. 65(2)113-121(2000)
UDC 622.337:66.094.3:547.979.733
JSCS-2732
Original scientific paper

Air oxidation of the kerogen/asphaltene vanadyl porphyrins: an electron spin resonance study

PAVLE I. PREMOVIC, IVANA R. TONSA, DRAGAN M. DJORDJEVIC and MIRJANA S. PAVLOVIC*

Laboratory for Geochemistry and Cosmochemistry, Department of Chemistry, Faculty of Science, University of Nis, P.O.Box 91, YU-18000 Nis, and
*Vinca Institute of Nuclear Sciences, P.O.Box 522, YU-11001 Belgrade, Yugoslavia

(Received 30 June 1999)
The thermal behavior of vanadyl porphyrins was studied by electron spin resonance during heating of kerogens, isolated from the La Luna (Venezuela) and Serpiano (Switzerland) bituminous rocks, at 25°C for 1 to 20 days in the presence of air. During the thermal treatment of the kerogens, the vanadyl porphyrins resonance signals decrease monotonically and become quite small after 6 days of heating. Concomitantly, new vanadyl signals appear and, at longer heating times, dominate the spectrum. It is suggested that the secondary vanadyl species must have been formed from vanadyl porphyrins. Similar conversions of vanadyl porphyrins are observed under the same experimental conditions for asphaltenes extracted from the La Luna and Serpiano rocks, and floating asphalt from the Dead Sea (Israel). A comparison of the spin-Hamiltonian parameters for vanadyl porphyrins and the vanadyl compounds obtained during pyrolysis of the kerogens/asphaltenes suggests that the latter are of a non-porphyrin type. For comparison a study was conducted on Western Kentucky No. 9 coal enriched with vanadium (>>400 ppm) from six mines. All the coal samples show only the presence of predominant by non-porphyrin vanadyl compounds, similar to those generated through laboratory heating of the kerogens/asphaltenes in air. In addition, some samples also contain a minor amount of vanadyl porphyrins.
Keywords: vanadyl porphyrins, kerogen, asphaltene, incorporation, electron spin resonance.

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J. Serb. chem. Soc. 65(2)123-130(2000)
UDC 547.962.3:534.321.9:66.084.8
JSCS-2733
Original scientific paper

Determination of the critical molar mass of ovalbumin oligomers degraded by ultrasound

DRAGANA FILIPOVIC, MARIJA RADOJCIC and BRATOLJUB H. MILOSAVLJEVIC

Vinca Institute of Nuclear Sciences, P.O.Box 522, YU-11001 Belgrade, Yugoslavia

(Received 26 May, revised 28 September 1999)
An experimental method has been developed which enables the determination of the critical molar mass (Mmc) of ovalbumin oligomers degraded by ultrasound of known frequency. To test the validity of the Mmc postulate, a series of ovalbumin oligomers was prepared by the radiolytic cross-linking of 1% solutions of ovalbumin monomer dissolved in 50 mM Na/K-phosphate buffer pH 7.0 saturated with N₂O. Under these conditions, irradiation with 5 kGy from a ⁶⁰Co source, yielded ovalbumin dimers, trimers, tetramers, and higher order oligomers. On the basis of the results obtained with the ovalbumin oligomers, it was concluded that for ultrasound of 23 kHz frequency and 5mm amplitude, the Mmc was 274000 + 14000 g/mol. Our results confirmed that the two postulates in the chemistry of polymer degradation by ultrasound are valid when ovalbumin oligomers are used as substrates, i.e., (1) that the higher the molar mass of the original macromolecule, the faster is its degradation rate, and (2) that a lower molar mass limit (LMmL) exists below which the macromolecules are resistent to further degradation.
Keywords: ovalbumin, ultrasound, critical molar mass.

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J. Serb. Chem. Soc. 65(2)131-140(2000)
UDC 618.36:547.963:541.18.04-004.12
JSCS-2734
Original scientific paper

Isolation and characterization of galectin-1 binding proteins from human placenta

MIROSLAVA JANKOVIC

Institute for the Application of Nuclear Energy, INEP, Banatska 31b, YU-11080 Zemun, Yugoslavia

(Received 30 June 1999)
Galectin-1 binding proteins were isolated from human placenta by affinity chromatography on a column with immobilized endogenous lectin. The molecular masses of the isolated proteins of 170, 67 and 56 kDa were estimated by gel filtration and SDS-PAGE. These proteins were characterized as galactose-containing glycoproteins, based on their reactivity with Ricinus communis agglutinin. In addition, sialylated-lacto-N-fucopentaose II was detected in the 170 kDa protein, using anti CA 19-9 monoclonal antibodies. The interaction of the isolated proteins with human placental galectin-1 was investigated by a solid phase binding assay using asialofetuin as the glycoprotein ligand. The 67 kDa and 56 kDa proteins were found to inhibit galectin-1 binding of asialofetuin, whereas the 170 kDa protein had the opposite effect. It caused an increase in the binding of asialofetuin, suggesting a positive cooperative binding.
Keywords: galectin-1, human placenta, affinity chromatography, RCA I, CA19-9.

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J. Serb. Chem. Soc. 65(2)141-145(2000)
UDC 611.637:576.8.097:547.953.2
JSCS-2735
Short communication

SHORT COMMUNICATION
Investigation of prostate specific antigen glycosylation

VESNA MARINOVIC and MARGITA CUPERLOVIC

Institute for the Application of Nuclear Energy-INEP, Banatska 31b, YU-11080 Zemun, Yugoslavia

(Received 15 March 1999)
In the present work, prostate specific antigen (PSA) glycosylation was examined by lectin affinity methods. The results obtained indicated that PSA purified from human seminal plasma contained at least one bianntenary N-linked oligosaccharide chain, which was composed of the monosaccharides manose, galactose, N-acetylgalacto-samine, fucose and sialic acid. No O-linked carbohydrate chains were detected.
Keywords: prostate specific antigen, PSA glycosylation, lectins.

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