title: Oxidation of tetrahydro-beta-carboline by cytochrome P-450cam--determination and rationalisation of product distribution.
abstract: Cytochrome P-450cam oxidises 1,2,3,4-tetrahydro-beta-carboline, an indolic alkaloid. We report here measurements of the product distribution of this oxidation. To rationalise the experimental results, ab initio quantum-chemistry calculations of the product stabilities and molecular-dynamics calculations of the substrate-binding mode in the active site were performed. The calculations suggest that the product distribution is influenced by both the relative intrinsic gas-phase stabilities of the monohydroxy products and by conformational rearrangement of the active site on substrate binding.
authors.affiliation: Section de Biophysique des Protéines et des Membranes, DBCM, CEA-Saclay, Gif-sur-Yvette, France.
authors.forename: J
authors.initials: J
authors.lastname: Sopková-de Oliveira Santos
authors.forename: J C
authors.initials: JC
authors.lastname: Smith
authors.forename: M
authors.initials: M
authors.lastname: Delaforge
authors.forename: H
authors.initials: H
authors.lastname: Virelizier
authors.forename: C K
authors.initials: CK
authors.lastname: Jankowski
mesh_terms: D001665:Binding Sites; D019475:Camphor 5-Monooxygenase / Q000737:chemistry* / Q000378:metabolism*; D002243:Carbolines / Q000737:chemistry / Q000378:metabolism*; D019363:Cytochrome P-450 CYP1A1 / Q000737:chemistry* / Q000378:metabolism*; D013058:Mass Spectrometry / Q000379:methods; D008958:Models, Molecular; D010084:Oxidation-Reduction; D011487:Protein Conformation
chemical_list: D002243:Carbolines; C009804:tryptoline; D019363:Cytochrome P-450 CYP1A1; D019475:Camphor 5-Monooxygenase