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Appl Microbiol Biotechnol

Title:		CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase
Author(s):		Ly TT; Khatri Y; Zapp J; Hutter MC; Bernhardt R;
Address:		"Department of Biochemistry, Saarland University, 66123 Saarbrucken, Germany"
Journal Title:		Appl Microbiol Biotechnol
Year:		2012
Volume:		20120106
Issue:		1
Page Number:		123 - 133
DOI:		10.1007/s00253-011-3727-z
ISSN/ISBN:		1432-0614 (Electronic) 0175-7598 (Linking)
Abstract:		"Many terpenes and terpenoid compounds are known as bioactive substances with desirable fragrance and medicinal activities. Modification of such compounds to yield new derivatives with desired properties is particularly attractive. Cytochrome P450 monooxygenases are potential enzymes for these reactions due to their capability of performing different reactions on a variety of substrates. We report here the characterization of CYP264B1 from Sorangium cellulosum So ce56 as a novel sesquiterpene hydroxylase. CYP264B1 was able to convert various sesquiterpenes including nootkatone and norisoprenoids (alpha-ionone and beta-ionone). Nootkatone, an important grapefruit aromatic sesquiterpenoid, was hydroxylated mainly at position C-13. The product has been shown to have the highest antiproliferative activity compared with other nootkatone derivatives. In addition, CYP264B1 was found to hydroxylate alpha- and beta-ionone, important aroma compounds of floral scents, regioselectively at position C-3. The products, 3-hydroxy-beta-ionone and 13-hydroxy-nootkatone, were confirmed by (1)H and (13)C NMR. The kinetics of the product formation was analyzed by high-performance liquid chromatography, and the K ( m ) and k (cat) values were calculated. The results of docking alpha-/beta-ionone and nootkatone into a homology model of CYP264B1 revealed insights into the structural basis of these selective hydroxylations"
Keywords:		"Biotechnology Cytochrome P-450 Enzyme System/chemistry/genetics/*metabolism Kinetics Mixed Function Oxygenases/chemistry/genetics/*metabolism Models, Molecular Myxococcales/*enzymology/genetics Norisoprenoids/chemistry/*metabolism Polycyclic Sesquiterpene;"
Notes:		"MedlineLy, Thuy T B Khatri, Yogan Zapp, Josef Hutter, Michael C Bernhardt, Rita eng Research Support, Non-U.S. Gov't Germany 2012/01/10 Appl Microbiol Biotechnol. 2012 Jul; 95(1):123-33. doi: 10.1007/s00253-011-3727-z. Epub 2012 Jan 6"