UCSD CHEM 259 - Medicinal Chemistry of Modern Antibiotics (18 pages)

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Medicinal Chemistry of Modern Antibiotics



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Medicinal Chemistry of Modern Antibiotics

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Lecture Notes


Pages:
18
School:
University of California, San Diego
Course:
Chem 259 - Special Topics in Organic Chemistry
Special Topics in Organic Chemistry Documents

Unformatted text preview:

Chemistry 259 Medicinal Chemistry of Modern Antibiotics Spring 2008 Lecture 7 Antibiotics Classes Targets Part II Drugs Targeting Fatty Acid and Folic Acid Biosynthesis Cell Division Thomas Hermann Department of Chemistry Biochemistry University of California California San Diego Antibacterial Targets Overview Bacterial Fatty Acid Biosynthesis Bacterial Fatty Acid Biosynthesis Bacterial Fatty Acid Biosynthesis Bacterial Fatty Acid Biosynthesis Bacterial Fatty Acid Biosynthesis Bacterial Fatty Acid Biosynthesis Bacterial Fatty Acid Biosynthesis Inhibitors BP1 Decynoyl NAC Bacterial Fatty Acid Biosynthesis FabI Inhibitors broadspectrum antibacterial used in soap soap disinfectant used to treat M tuberculosis for over 50 years Gram M tuberculosis not used in human toxic FabI FabI Bacterial Fatty Acid Biosynthesis FabI Inhibitors broadspectrum antibacterial used in soap soap disinfectant NAD used to treat M tuberculosis for over 50 years NAD Gram M tuberculosis not used in human toxic NAD Isoniazid FabI inhibitors bind to the active site of the reductase and form a tight complex with the NAD cofactor NAD nicotinamide adenine dinucleotide Triclosan Diazaborine Bacterial Fatty Acid Biosynthesis FabI Inhibitors Isoniazid Broussy et al Org Biomol Chem 2005 3 670 Bacterial Fatty Acid Biosynthesis FabI Inhibitors Triclosan NAD Triclosan Stewart et al JMB 1999 290 859 Bacterial Fatty Acid Biosynthesis FabI Inhibitors Diazaborines NAD Levy et al JMB 2001 309 171 Bacterial Fatty Acid Biosynthesis FabB Inhibitors isolated from fungus Nocardia sp efficacious against G G in mouse models isolated from fungus Cephalosporium ceruleans inhibits also mammalian fatty acid synthases not used FabB Thiolactomycin occupies malonate portion of the substrate binding site in FabB Cerulein mimics the covalently bound condensation intermediate nonpolar tail is located in a hydrophobic tunnel Heath et al Appl Microbiol Biotechnol 2002 58 695 Bacterial Fatty Acid Biosynthesis FabA Inhibitors



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