Amino glycosidation

The hexanuclear Ir111 complex [L IrCl2cp 6], in which L is based on the amino glycoside neomycin B (249), has been characterized by IR, 13C, and 31P NMR spectroscopy, and by FAB Ms419 The in vivo antitumor and antitrypanosomal effects of [IrY4Cl2]1 complexes,... 

Walter, R, Vicens, Q. and Westhof, E. (1999). Amino-glycoside-RNA interactions. Curr. Opin. Chem. Biol. 3, 694-704. 

Bacteria overall > 410 Groom, 1992 Scarce diversification between land and sea. ALKAL. indole, phenazine, pyperazine, pyrrole, polypyrrole. PEPT. various classes, including siderophores. POLYKET. lactones, macrolides, quinones. CARBOH. (amino)glycoside, terpenoids hi hi ... 

C Chemical Shifts and Conformational Changes Observed on Protonation of Amino-Glycosides. R. U. Lemieux, S. Koto, and B. Y. Chung, Abstr. 2nd Joint Conf. CIC/ACS, Montreal, May 30-June 2 (1977), CARS 4. 

The fourth chapter concerns a family of radical reactions which were invented to solve the problem of how to remove secondary hydroxyl groups in complicated amino-glycoside antibiotics. This biologically important problem was solved by the invention of a new reaction. It changed carbohydrate chemistry and introduced many chemists to high yielding radical reactions for the first time. 

Amino glycosides.1 Furanoid or pyranoid glycals (2) when irradiated with this azodicarboxylate undergo a [4 + 2]cycloaddition to form a dihydrooxadiazine (3) in 70-80% yield. The adducts on treatment with methanol (TsOH) open with inversion at C, to give hydrazines (4), which furnish 2-amino glycosides (5) on hydrogenolysis and deprotection. 

Treatment of the adducts with catalytic amounts of p-toluene sulfonic acid in methanol results in formation of the corresponding methylglycosides (23a-d) arising from inversion at C-l. Hydro-genolysis of compounds (23a-d) then yields the 2-amino glycosides. 

A transglutaminase reaction was found to be useful in the preparation of neoglycoproteins. For example, oo-amino glycosides were used as a substrate for transglutaminase for the addition of carbohydrates to glutamine side chains (35, 36). The success of this reaction, however, seems somewhat unpredictable. 

Smith CR, Lietman PS. Effect of furosemide on amino-glycoside-induced nephrotoxicity and auditory toxicity in humans. Antimicrob Agents Chemother 1983 23(l) 133-7. 

An interesting example of a branched trimer containing (1 6)- and /3(1 2)-amide-linked sugars was supplied by Sicherl and Wittmann who devised mimetics of amino glycosides [37]. Pioneered by the group of Kessler [38] pyranoid sugar amino acid templates were described to represent turn mimetics and model peptides [39,40] including cyclic peptides [41,42]. As... 

Pelyvas, I. F., Madi-Puskas, M., Toth, Z. G., Varga, Z., Hornyak, M., Batta, G., Szlaricskai, F. Synthesis of new pseudo-disaccharide amino glycoside antibiotics from carbohydrates. J. Antibiot. 1995, 48, 683-695. 

Gentamicin. — This 2-deoxystreptamine-containing amino-glycosidic antibiotic is related to the neomycins, the paromomycins and kanamycin. Clinical reports indicated gentamicin is a drug of choice for parenteral and topical treatment of infections caused by Pseudomonas aeruqinosa 4 and Proteus mirabilis. Forty-seven of 50 patients topically treated for various bacterial infections were cleared of... 

R = Me) (Lafont and Descotes 1988). The amino glycoside is then obtained by hydrazinolysis. Treatment of protected glycals with benzenesulfon-amide and iodonium dicollidine perchlorate gave compounds 10.49. Again, the corresponding aziridines were not isolated but the expected product of opening... 

CD Ashby, JE Lewis, JC Nelson. Measurement of 3 amino glycoside antibiotics with a single radioimmunoassay system. Clin Chem 24 1734, 1978. 

A Broughton, JE Strong, LK Pickering, J Knight, GP Bodey. Radioimmunoassay and radioenzymatic assay of a new amino glycoside antibiotic netilmicin. Clin Chem 24 717, 1978. 

Butirosiu. Am bury rosin. C2 H4 NsOn mol wi 555.60. C 45.40%, H 7.44%, N 12.60%, O 34.56%. Amino-glycosidic antibiotic complex obtained from fermentation filtrates of mucoid strains of JhtciJfus circulans (NRRL B-3312 and B-3313). Consists of two components, butiro-sin A (80-85%) and butirosin B (15-20%), isomers which differ only in the configuration at one carbon atom in the pentose moiety. Prepn Woo er ah, Ger. pat. 1,914,527... 

Seeberger et al., 1997 Lehmann, 1976, 1996). Glycals are versatile synthetic intermediates in the synthesis of 2-deoxy- and 2-amino-glycosides (see Scheme 4.4.5) (Fraser-Reid, 1975 Fraser-Reid and Anderson, 1980). Reaction of glycal and alcohol in the presence of promoters (Ag+/1, NBS) and subsequent reductive dehalogenation (Hj-Pd, Bu SnH-AiBN) produces preferentially the 2-deoxy-(-glycoside. 

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