
TY  - JOUR
A1  - Henderson, SA 
A1  - Oconnor, J 
A1  - Rendina, AR 
A1  - Savage, GP 
A1  - Simpson, GW 
T1  - The Synthesis and Biological Activity of 'Crippled Biotin'
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1995
VL  - 48
IS  - 12
SP  - 1907
EP  - 1916
KW  - 
UR  - https://doi.org/10.1071/CH9951907 
N2  - (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. 
ER  -

