63 新カルバペネム系抗生物質C-19393の化学

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The absolute configuration at the sulfoxide of 5,6-cis-carbapenem antibiotics is discussed on the basis of chemical reactions and CD spectral data. Some stereoisomers at the side chain were synthesized from 1 by the combination of hydrogenation, oxidation and Z, E-isomerization. The CD sectral studies revealed that the Cotton effects of the stereoisomers indicated clear opposite signs at both 260-275 and 280-300nm regions. Further CD spectral studies on the derivatives elucidated that these Cotton effects may reflect two chromophores; -CH-S(O)-CH=CH-NH- for the former region and -CH_2-S(O)-C=C-CCO^- for the latter. In conclusion, these naturally occurring 5,6-cis-carbapenem antibiotics have been shown to possess the R-configuration at the sulfoxide. Naturally occurring carbapenem antibiotics having a double bond on the side chain refluxed in chloroform containing quarternary alkyl ammonium halide, were converted to Z-isomers in high yields. The mechanism of this new equilibration involves intramolecular proton transfer from the carboxylic acid to the carbon α to the sulfur atom in the side chain as shown by deuterium labeling experiments. Some Z-isomers showed stronger protective effects in mice infected by E.coli O-111 and more potent synergistic activities with cefotiam in mice infected by P.vulgaris GN4815 than did the naturally occurring E-isomers. The decomposition rates of Z-isomers in mouse kidney homogenates were about 3-fold slower than those of E-isomers.
天然有機化合物討論会の論文
1982-09-10

63 新カルバペネム系抗生物質C-19393の化学

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