Synthesis and biochemical properties of Z- and E-4,5-dehydrodethiobiotin.
Radical species are postulated intermediates in the formation of the carbon-sulfur bonds of biotin. It was of interest to examine the behaviour of unsaturated analogues which should give rise to allylic radicals. The two isomers of 4,5-dehydrodethiobiotin have been synthesized and labelled with 14C on their carboxylic acid group. When incubated with an in vitro system capable of transforming dethiobiotin into biotin, they covalently label biotin synthase.
Jestin
E
E
Laboratoire de Chimie Organique Biologique, Université P. et M. Curie, URA CNRS 493, Paris, France.
Moreau
F
F
Florentin
D
D
Marquet
A
A
D001710:Biotin / Q000031:analogs & derivatives / Q000378:metabolism; D002855:Chromatography, Thin Layer; D004591:Electrophoresis, Polyacrylamide Gel; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013466:Sulfurtransferases / Q000378:metabolism
C103396:4,5-dehydrodethiobiotin; D007093:Imidazoles; D001710:Biotin; C004749:desthiobiotin; D013466:Sulfurtransferases; C057985:biotin synthetase