4.5 Article

A thiolate ligand on a cytochrome P-450 mimic permits the use of simple environmentally benign oxidants for biomimetic steroid hydroxylation in water

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 15, Issue 24, Pages 5463-5466

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2005.08.090

Keywords

cyclodextrin; hydrophobic binding; porphyrins

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Manganese porphyrin systems carrying cyclodextrin binding groups can regioselectively and stereo selectively hydroxylate bound steroid substrates, using iodosobenzene as oxidant, but hydrogen peroxide and other simple oxidants Such as sodium hypochlorite are not effective in water. Thiol ligands were then added to the catalyst, both covalently attached and hydrophobically bound, and with these ligands hydrogen peroxide was now an effective oxidant. (c) 2005 Elsevier Ltd. All rights reserved.

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