Glycosides of hydroxylamine derivatives: I. Phase transfer synthesis and the study of the influence of glucosaminides of isatine 3-oximes on bacterial luminescence

Abstract

In the phase transfer system solid calcium carbonate-acetonitrile, per acetate alpha-D-glucosaminilchloride glycosilate easily deprotoned isatine-3-oximes hydroxyl groups. It was found that the presence in the reaction mixture a catalytic amounts of 15-crown-5 accelerated the process twice. Obtained O-beta-D-glucosaminides were identified with 1H-NMR spectroscopy. Features of synthesized compound's NMR spectra are discussed in comparison with those of another N-acetylglucosamine 1-O-derivatives. The biological activity of the some oximes with different substituents in isatin residuum has been studied in a test of inhibition of bioluminescence of marine luminescent bacteria Photobacterium leiognathi Sh12. The nature of N-substituent of isatin fragment and 5-substituent of isatin main structure is compared with glycosides ability to suppress bacterial luminescence.

Synthesis and investigation of antimicrobial activity of 8-hydroxyquinoline glucosaminides

“…The highest level of biolumines cence inhibition was recorded for the minimal (0.05 mg/mL) concentration of compounds (IX) and (X). The reasons for such dependence are not clear though they were earlier noted for some glu cosaminides, the biological activity of which was stud ied in the same test [16,17].…”

“…Full acetates (V)-(VII) were deacetylated according to Zemplen using the method [16,17] to form triols (VIII)-(X). Completeness of the О acetyl protective group removal was assessed by 1 Н NMR spectroscopy (table) and HPLC.…”

“…Comparative investigation of the bactericidal activ ity of glycosides (VIII)-(X) and initial hydroxyquino lines (II)-(IV) was conducted using the method of bioluminescence inhibition with the strain of marine luminous bacteria Vibrio fischeri F1 (NRRL B 11177), as was described earlier [16,17].…”

“…1 H NMR spectra were recorded with the spectrom eter Varian VXR 300 (300 MHz), internal standard Acetonitrile and K 2 CO 3 were prepared as described earlier in [17].…”

Tungsten oxide: a catalyst worth studying for the abatement and decontamination of chemical warfare agents

“…Finally, aiming at a real on-field use, where a total-loss dispersion of solid decontamination mixtures is likely, the potential impact of the catalysts on the environment was evaluated by three main kinds of biotests, as rapid, costeffective and sensitive screening tools: (i) the marine bioluminescent bacterium, P. leiognathi Sh1, isolated from Azov Sea, was utilised as a target organism to assess the direct toxic impact on living organisms (Katsev, 2014;Kuryanov, Chupakhina, Shapovalova, Katsev, & Chirva, 2011); (ii) the potential mutagenic properties of the solids and their ability to generate toxic oxygen radicals were evaluated by luminescent bioreporter strains of Escherichia coli MG1655, with the lux CDABE operon from Photorhabdus luminescens (Chugunova et al, 2016(Chugunova et al, , 2015Zavilgelsky, Kotova, Yu, & Manukhov, 2007); and (iii) the potential detrimental impact of the solids on vegetable plants was evaluated by studying the effects on the chlorophyll fluorescence and on germination parameters on P. vulgaris L., as a model plant (common bean plants) (Maxwell & Johnson, 2000).…”