Amino-glycoside Antibiotics

New representatives of known groups of compounds have been reported. Antibiotic BMY-28251, obtained from a Bacillus pumilis strain, has been identified as 3,3 -neotrehalosdiamine (1), the first example of an Of,y3-trehalose antibiotic. New components of a validamycin 

A synthesis of the pseudotrisaccharide destomycin C has been described, using mannose and deoxystreptamine to form a pseudodisaccharide which was then coupled to destonic acid to form the orthoester linkage inversion at the mannose C-4 centre gave the antibiotic. 

Syntheses from antibiotic precursors have been recorded for 6 -deoxy-6 -fluoro-kanamycin A and -amikacin using DAST, and also for 1-N-[(R) and (RS)-3-amino-2-fluoropropanoyll kanamycin. DAST was also used to make 2, 3-dideoxy-2-fluorokanamycin A (12) and its 

Synthesis of amino-sugars present in amino-glycoside antibiotics is also referred to in Chapter 9. 

A comparative study of desorption chemical ionization m.s. with molecular secondary ion m.s. as applied to amino-glycoside antibiotics has been published a combination of these methods allowed unequivocal characterization of compounds containing an aminoacyl group. 

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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. 

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... 

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... 

The synthesis of 6-epz-purpurosamine B and other amino-sugar components of amino-glycoside antibiotics is referred to in Chapter 8. 

Lori, R., Aruna, J.K., Arunachalam, J., 2012. Highly stable, protein capped gold nanoparticles as effective drug delivery vehicles for amino-glycosidic antibiotics. Mater. Sci. Eng. 32 (6), 1571-1577. 

Numerous reports describe the modification of natural amino-glycoside antibiotics or products derived from them by conventional methods. 1-/ -Alkylated kanamycins can be prepared very efficiently by utilizing an O N acyl migration to protect the sugar amino-groups selectively, leaving the deoxy-streptamine amino-groups free-, a formylation-deformylation sequence then... 

New amino-glycoside antibiotics saccharocin and KA-5685, isolated from strains of Saccharopolyspora, have been shown to be 4"-deamino-4"-hydroxyapramycin (6). A total synthesis of apramycin... 

A new amino-glycoside antibiotic, boholmycin (1), has been isolated from a strain of S. hygroscopicus the pseudo-tetrasaccharide contains a heptose, two amino-sugars, and dicarbamoyl-scyllo-inositol. A complex of antibiotics produced by a strain of S. fradiae, "dekamycin", has been shown by m.s. and n.m.r. techniques... 

The structures and syntheses of amino-glycoside antibiotics and the mode of action and of inactivation of these antibiotics have been reviewed. Reviews have also appeared on the chemistry and conformation of tobramycin/ and on the structure of, and clinical resistance to, sisomycin and the gentamycin group of antibiotics. ... 

Amino-glycoside antibiotics have been reviewed. 

Park, W.C., Auer, M., Jaksche, H. and Wong, C.H., Rapid combinatorial synthesis of amino glycoside antibiotic mimet-ics Use of a polythylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA rev responsive element, J. Am. Chem. Soc., 118 (1996) 10150-10155. 

Chlorobenzoate, 3-methyl-4-nitro-phenol, and the detergents sodium lauryl sulfate and Tween 80 had increased toxicity with the addition of calcium and EDTA. No correlation between the structure of the chemical and the effect of EDTA and calcium could be ascertained. For example, streptomycin and neomycin are bofli amino glycoside antibiotics. Calcium and EDTA did not affect the toxicity of Streptomycin but nearly eliminated the toxicity of Neomycin. 

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