Australian Journal of Chemistry p. 1907 - 1916 (1995)
Update date:2022-08-02
Topics:
Henderson, Scott A.
O'Connor, Jacqueline
Rendina, Alan R.
Savage, G. Paul
Simpson, Gregory W.
(3aα,6β,6aα)-6-Methyltetrahydro-1H-thieno<3,4-b>pyrrol-2(3H)-one (2) was prepared as a crippled analogue of biotin.The key synthetic step involved hydrogenation of 6-methyl-1H-thieno<3,4-b>pyrrol-2(3H)-one on palladium to introduce the necessary all-cis configuration.Both compounds were weak inhibitors of the biotin-dependent wheat acetyl-CoA carboxylase compared to substrates or the potent herbicidal inhibitors of this enzyme, but were more potent than biotin or imidazolidone.Neither compound inhibited the biotin-dependent transcarboxylase component of bacterial acetyl-CoA carboxylase, nor did they significantly inhibit the growth of Arabidopsis thaliana.
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