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

• Published in: Bioorganicheskaia khimiia Vol. 37; no. 2; p. 259
• Main Authors: Kur'ianov, V O, Chupakhina, T A, Shapovalova, A A, Katsev, A M, Chirva, V Ia
• Format: Journal Article
• Language: Russian
• Published: Russia (Federation) 01.03.2011
• Subjects: Acetonitriles - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - metabolism; Anti-Bacterial Agents - pharmacology; Calcium Carbonate - chemistry; Catalysis; Crown Ethers - chemical synthesis; Glucosides - chemical synthesis; Glucosides - metabolism; Glucosides - pharmacology; Hydroxylamine - chemical synthesis; Hydroxylamine - metabolism; Isatin - analogs & derivatives; Isatin - chemical synthesis; Isatin - metabolism; Isatin - pharmacology; Luminescence; Luminescent Measurements; Magnetic Resonance Spectroscopy; Phase Transition - drug effects; Photobacterium - drug effects; Photobacterium - physiology
• ISSN: 0132-3423

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.