198560-58-6Relevant academic research and scientific papers
Geometrically directed selective steroid hydroxylation with high turnover by a fluorinated artificial cytochrome P-450
Breslow, Ronald,Gabriele, Bartolo,Yang, Jerry
, p. 2887 - 2890 (1998)
A metalloporphyrin has been synthesized carrying a beta-cyclodextrin group on tetrafluorophenyl rings at the four meso positions of the porphyrin. It performs the selective hydroxylation of an androstanediol derivative with complete positional selectivity
Catalytic oxidations of steroid substrates by artificial cytochrome p-450 enzymes.
Yang, Jerry,Gabriele, Bartolo,Belvedere, Sandro,Huang, Ying,Breslow, Ronald
, p. 5057 - 5067 (2007/10/03)
Catalysts comprising manganese-porphyrins carrying cyclodextrin binding groups are able to perform hydroxylations with substrate selectivity and regio- and stereoselectivity and high catalytic turnovers. The geometries of the catalyst/substrate complexes override intrinsic substrate reactivities, permitting attack on geometrically accessible saturated carbons of steroids in the presence of secondary carbinol groups and carbon-carbon double bonds, as in enzymatic reactions. Selective hydroxylations of steroid carbon 9 positions are of particular practical interest.
Biomimetic hydroxylation of saturated carbons with artificial cytochrome P-450 enzymes - Liberating chemistry from the tyranny of functional groups
Breslow, Ronald,Yang, Jerry,Yan, Jiaming
, p. 653 - 659 (2007/10/03)
Five mimics of cytochrome P-450 have been prepared and examined as catalysts for the specific hydroxylation of steroids. Reactions occur dictated by the geometries of the complexes, overcoming the intrinsic reactivity of a carbon-carbon double bond and of
