ORGN 916 |
| Novobiocin is an antimicrobial agent produced by Streptomyces species and was identified as a potent inhibitor of DNA gyrase which catalyzes the negative supercoiling of DNA in prokaryotes. Although novobiocin has been used clinically for the treatment of cancer for several years, it was only recently shown to inhibit the 90 kDA heat-shock proteins (HSP90), which is an emerging target for the development of new cancer chemotherapeutics. The noviose, subunit of novobiocin, is a rare sugar moiety found solely in the coumarmycin family of antibiotics which is responsible for their remarkable biological activity. Here, we disclose a novel synthetic route to both enantiomers of noviose from the commercially available (-)-pantolactone in a minimal synthetic sequence. We have also demonstrated that our route can be used for the generation of noviose analogues which may exhibit better biological properties.
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Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 134, Oral
Division of Organic Chemistry |
