Synthesis and Antimicrobial Activity of Chiral cis-Cycloheximide Isomers |
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Authors: | Sachio Kudo Takayuki Oritani Kyohei Yamashita |
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Institution: | Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University, Sendai 980, Japan |
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Abstract: | Such (+)- and (?)-cis-cycloheximide isomers as isocyclohcximide (1a, 1b), α-epiisocycloheximide (2a, 2b) and neocycloheximide (3a, 3b) were synthesized by aldol condensation of (?)-(2R, 4R)- and (+)-(2S, 4S)-cis-2,4-dimethyl-1-cyclohexanone (5a, 5b). obtained by microbial resolution, with 4-(2-oxoethyl)-2,6-piperidinedione (7). The absolute configuration of the (?)-cis-ketone 5a was confirmed by chemical correlation with natural (2S, 4S, 6S, αR)-cycloheximide (4). The newly synthesized isomer, (?)-α-epiisocycloheximide (2b), showed strong antimicrobial activity against S. cerevisiae andP. oryzae close to that of natural cycloheximide (4). |
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Keywords: | bioluminescence chimeric protein fatty acyl-CoA synthetase firefly luciferase |
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