172889-33-7Relevant academic research and scientific papers
The Synthesis and Biological Activity of "Crippled Biotin"
Henderson, Scott A.,O'Connor, Jacqueline,Rendina, Alan R.,Savage, G. Paul,Simpson, Gregory W.
, p. 1907 - 1916 (1995)
(3aα,6β,6aα)-6-Methyltetrahydro-1H-thienopyrrol-2(3H)-one (2) was prepared as a crippled analogue of biotin.The key synthetic step involved hydrogenation of 6-methyl-1H-thienopyrrol-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.
