66319-07-1Relevant 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 (2007/10/02)
(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.
Stereoisomeric Flavor Substances XXXI. - Tetrahydro-2-methylthiophen-3-ol - Structure and Properties of the Stereoisomers
Mosandl, Armin,Hener, Uwe,Fenske, Heinz-Dieter
, p. 859 - 862 (2007/10/02)
Tetrahydro-2-methylthiophen-3-ol (6) has been synthesized and separated by liquid chromatography to yield cis(6a/6a') and trans isomers (6b/6b').Using (S)-tetrahydro-5-oxo-2-furancarboxylic acid chloride, 6a/6a' and 6b/6b' are transformed into the diastereomeric esters 7 - 10 which are separated by liquid chromatography.Hydrolysis of the esters yields the optically pure stereoisomers 6a, 6a', 6b, and 6b'.Absolute configuration and sensory characteristics of these stereoisomers are given.
