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The acidic functions of the tetracyclines are capable of forming salts through chelation with metal ions. The salts of polyvalent metal ions, such as Ca2+, Mg2+, are all quite insoluble at neutral pHs. Chelation Section 3 Aminoglycoside Antibiotics The antibiotics contains a pharmacophoric 1,3-diamino inositol moiety: either streptamine, 2-deoxystreptamine, or spectinamine. Several of the alcoholic function of the 1,3-diaminoinositol are substituted through glycosidic bonds with characteristic aminosugars to form pseudo-oligosaccharides. Actions and Uses The antibiotics that are basic and form acid addition salts, are not absorbed in significant amounts from the gastrointestinal tract, and are excreted in active form in the urine. The toxicities involve ototoxicity to functions mediated by the eighth cranial nerve and kidney tubular necrosis producing decreases in glomerular function. Streptomycin An axial hydroxyl group at C-2 and two highly basic guanido groups at C-1 and C-3 in place of the primary amine moieties of 2-deoxystreptamine. It was introduced in 1943 primarily for the treatment of tuberculosis. Selmon Waksman, the discoverer of streptomycin, received a Nobel Prize in 1952. Section 4 Macrolide Antibiotics This antibiotic family have two or more characteristic sugars attached to the 14-membered ring. One of these sugars usually carries a substituted amino group so their chemical character is weakly basic. They are not very water-soluble as free bases but salt formation with certain acids. Mechanism of Action The macrolides inhibit bacteria by interfering with ribosomal protein biosynthesis. More recent studies suggest that the macrolides inhibit protein synthesis by binding to domain V of the bacterial 23S rRNA making contact with adenosine 2058 (A2058). Erythromycin Erythronolide desosamine cladinose The connection of cladinose to oxygen at 3-postion in erythronolide The connection of desosamine to oxygen at 5-postion in erythronolide Chem