Aminoglycosides kanamycin classes

Figure 4.1. Structures of neomycin and kanamycin classes of aminoglycosides.

It has been shown that the stereochemistry of the glycosidic bond to which the carbohydrate component is attached at the neamine core is essential for antibacterial activity. The neomycin class aminoglycoside consists of a neamine core and a P-linked carbohydrate component attached at the 0-5 position, while the kanamycin class aminoglycoside consists of a neamine core with a-linked carbohydrate component attached at the 0-6 position. Since neamine is the pivotal component of both neomycin and kanamycin, a readily accessible library of nnnsnal sugars will provide opportunity for the facile construction of both classes of aminoglycosides via glycosylation approach. 

Metal-chelating method has also been commonly employed for the regios-elective incorporation of AHB at N-1 of kanamycin class aminoglycoside (Scheme 4.20). Other kanamycin derivatives have been prepared in similar fashion (Figure 4.10). ... 

Scheme 4.20. Synthesis of kanamycin class of aminoglycosides with N-1 AHB.

Figure 4 Exemplar structures of various antibiotic classes that bind to either the 505 or the 305 subunit. Macrolides azithromycin (1), oxazolidinones linezolid (2), aminoglycosides Kanamycin A (3), Pleuromutilin (4), phenylpropanoids chloramphenicol (5), lincosamides clindamycin (6), Sparsomycin (7), Anisomycin (8), and tetracycline (9). See Scheme 9 for thiosptrepton (38). Not pictured streptogramins such as quinupristin/dalfopristin.

Glycodiversification for the Synthesis of Neomycin and Kanamycin Class Aminoglycoside Antibiotics... 

Example. Kanamycin is a member of the aminoglycoside class of antibiotics, all of which are eliminated exclusively by glomerular filtration. Creatinine is a natural body substance that is cleared almost exclusively by glomerular filtration, and creatinine clearance rate is frequently used as a diagnostic tool to determine glomerular filtration rate. The relationship... 

AND ANTIBACTERIAL ACTIVITY OF KANAMYCIN AND NEOMYCIN CLASS AMINOGLYCOSIDE ANTIBIOTICS... 

Figure 4.7. Phosphorylation of kanamycin and neomycin classes of aminoglycosides by APH(3 ).

Attaching fnnctionalities at the N-1 position of the 2-deoxystreptamine among kanamycin or neomycin class antibiotics, is one of the other most effective methods of reviving the activity against aminoglycoside resistant bacteria. This strategy has led to the development of semisynthetic amikacin that has an (5 )-4-amino-2-hydroxybutyryl (AHB) group at N-1 position. 

The synthesis of kanamycin and neomycin class aminoglycosides with N-... 

Cowan and co-workers ° have extensively characterized the Cu " complexes of two different classes of aminoglycosides—namely, kanamycin A (4) and neomycin B (2)—in addition to the neamine (1) class of aminoglycosides. Their findings, based upon the interaction of CUSO4 with kanamycin A and neomycin B, identified a blue monomeric 1 1 complex of Cu -kanamycin A as well as a dark green 1 2 complex Cu +-(kanamycin A>2 and a 1 1 Cu +-neomycin B complex, although the latter two were found to be less stable in aqueous solution with observable precipitation within 4 h. The Cu +-kanamycin A complex was found to be most stable in aqueous solutions over a period of one day. Based on C-13 and H-1 NMR relaxation experiments, the Cu -kanamycin A solution structure at pH = 7.9 (12) is described as Cu + coordinated to the... 

The phosphate backbone of both DNA and RNA provides a negatively charged template for attracting positively charged species. Drugs that commonly exploit this interaction are the aminoglycoside antibiotics. Examples include neomycin B (6.20) and kanamycin A (6.21) (Figure 6.12). This class of compounds binds rRNA in bacteria to interfere with translation of mRNA into functional proteins. 

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