
%0 Journal Article
%A Henderson, SA 
%A Oconnor, J 
%A Rendina, AR 
%A Savage, GP 
%A Simpson, GW 
%T The Synthesis and Biological Activity of 'Crippled Biotin'
%J Australian Journal of Chemistry
%D 1995/12/01
%V 48
%N 12
%P 1907-1916
%K 
%R https://doi.org/10.1071/CH9951907
%U https://www.publish.csiro.au/paper/CH9951907 
%X (3a&#945;,6&#946;,6a&#945;)-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. 
