Streptococcus pneumoniae antimicrobial resistance

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Fosfomycin is one of a few natural products containing a carbon-phosphorus (C— P) bond isolated from Streptomyces fradiae, Streptomyces viridochromogenes, and Streptomyces wedmorensis [73]. It was also isolated from Pseudomonas syringae and Pseudomonas viridiflava [74, 75], Fosfomycin is a highly effective antibiotic of low toxicity clinically utilized for the treatment of lower urinary tract infections [76] as well as methicillin-resistant [77] and vancomycin-resistant [78] strains of S. aureus. Moreover, fosfomycin is effective for the treatment of cephalosporin- and penicillin-resistant Streptococcus pneumonia [79] and ciprofloxacin-resistant E. coli [80], The antimicrobial activity of fosfomycin has been ascribed to the inactivation of UDP-GlcAAc-3-O-enolpyruvyltransferase (MurA), an essential enzyme that catalyzes the first committed step in the biosynthesis of peptidoglycan, the main component of the cell wall, by covalent alkylation of an active site cysteine [81]. 

Solithromycin (CEM-101, Figure 44.8) is a ketolide antibiotic undergoing clinical development for the treatment of community-acquired pneumonia. It is another example of semi-synthetic antimicrobial agents derived from erythromycin, which was designed to overcome erythromycin resistance in Streptococcus pneumoniae. The synthesis of solithromycin involves the introduction of the fluorine atom on the (3-keto ester moiety with Selectfluor in the presence of potassium tert-butoxide in tetrahydrofuran (THF). Solithromycin shows the greatest potency and widest spectrum of activity against respiratory tract... 

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