Aminoglycosides, synthesis

Scheme 17.25 Aminoglycoside synthesis through intramolecular aziridination.

Azides as Protecting Groups during Aminoglycoside Synthesis... 

The aminoglycosides exert their bactericidal effect by blocking a step in protein synthesis necessary for bacterial multiplication. They disrupt the functional... 

Spectinomycin (Trobicin) is chemically related to but different from the aminoglycosides (see Chap. 10). This drug exerts its action by interfering with bacterial protein synthesis. Spectinomycin is used for the treatment of gonorrhea... 

Bacterial ribosome function Aminoglycosides Tetracyclines Chloramphenicol Macrolides, azalides Fusidic acid Mupirocin Distort SOS ribosomal subunit Block SOS ribosomal subunit Inhibits peptidyl transferase Block translocation Inhibits elongation factor Inhibits isoleucyl-tRNA synthesis No action on 40S subunit Excluded by mammalian cells No action on mammalian equivalent No action on mammalian equivalent Excluded by mammalian cells No action on mammalian equivalent... 

Urease assay. When Proteus mirabilis grows in a urea-containing medium it hydrolyses the urea to ammonia and consequently raises the pH of the medium. This production of urease is inhibited by aminoglycoside antibiotics (inhibitors of protein synthesis Chapter 8). In practice, it is difficult to obtain reliable results by this method. 

B. Westermann and S. Domer, Synthesis of multivalent aminoglycoside mimics via the Ugi multicomponent reaction, Chem. Commun. (2005) 2116-2118. 

Protein synthesis inhibitors Chloramphenicol Tetracyclines Macrolides Lincosamides Aminoglycosides... 

Other key classes of antibacterials include the tetracyclines (Aureomycin, Terramycin), macrolides (erythromycin, Zithromax, Biaxin), and aminoglycosides (streptomycin, amikacin, neomycin). These antibacterials are protein synthesis inhibitors. 

Aminoglycoside a structurally complex antibacterial that works as bacterial protein synthesis inhibitor. 

E., Hofstadler, S. A., Griffey, R. H. Synthesis of neomycin analogs to investigate aminoglycoside—RNA interactions. Synlett 2003, 9,... 

E. E., Risen, L., Griffey, R. H. Design and synthesis of paromomycin-related heterocycle-substituted aminoglycoside mimetics based on a mass spectrometry RNA-binding assay. 

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