Stereostructure of a novel cytotoxic 18-membered macrolactone antibiotic FD-891.

Eguchi, Tadashi; Kobayashi, Kayako; Uekusa, Hidehiro; Ohashi, Yuji; Mizoue, Kazutoshi; Matsushima, Yoshitaka; Kakinuma, Katsumi

Eguchi, Tadashi; Kobayashi, Kayako; Uekusa, Hidehiro; Ohashi, Yuji; Mizoue, Kazutoshi; Matsushima, Yoshitaka; Kakinuma, Katsumi.

Affiliation

Eguchi T; Department of Chemistry and Materials Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan. eguchi@cms.titech.ac.jp

Org Lett ; 4(20): 3383-6, 2002 Oct 03.

Article in En | MEDLINE | ID: mdl-12323024

ABSTRACT

ABSTRACT

The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations. [structure see text]

Subject(s)

Anti-Bacterial Agents/chemistry; Anti-Bacterial Agents/toxicity; Macrolides; Magnetic Resonance Spectroscopy; Molecular Conformation; Molecular Structure; Stereoisomerism; X-Ray Diffraction

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