8-Thiabicyclo[3.2.1]octan-3-one as a biochemical tool in the study of tropane alkaloid biosynthesis
1991
Parr, A.J. | Walton, N.J. | Bensalem, S. | McCabe, P.H. | Routledge, W.
8-Thiabicyclo[3.2.1]octan-3-one, the sulphur analogue (replacing the methylaza bridge) of tropinone, was fed to Datura stramonium transformed root cultures. The compound was metabolized to a large degree. Notable products included the reduction product, 8-thiabicyclo[3.2.1]octan-3-ol, analogous to tropine, and also the derived 3-O-acetyl ester. In addition, tropane alkaloid synthesis was perturbed. Hyoseyamine levels, and in particular tropine and 3 alpha-acetoxytropane levels, were reduced. Pseudotropine, on the other hand, was found to increase in concentration. It is concluded that 8-thiabicyclo[3.2.1]octan-3-one may be a good biochemical tool in the study of tropane alkaloid biosynthesis.
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