Preparation and Evaluation of Furanomycin Analogs
Kellogg, Christopher M.
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This project consists of preparing and evaluating analogs of the antibiotic furanomycin. Furanomycin is an antibiotic which was isolated by Katagiri and co-workers from a culture filtrate of Streptomyaes threomyaetiaus. Three objectives were set up for this project. First, it was necessary to purify a crude preparation of furanomycin so that some pure starting material was available to prepare the analogs. Secondly, we desired to prepare the N-chloroacetyl derivative of furanomycin which could be used for x-ray crystallography to determine the absolute configuration of naturally occurring furanomycin. Our third objective was to racemize the L-furanomycin at carbon-2 while acylating the amino nitrogen, thus, providing both the N-acylated Land D isomers. The racemate could then be resolved by enzymatic methods to isolate the D isomer. Once isolated, we would biologically test the D and D,L forms for their antitumor and antibacterial properties to see how their activity compares to that of the L isomer.