Products from enzyme-catalyzed oxidations of norcarenes.

Products from enzyme-catalyzed oxidations of norcarenes. Research Abstract Details 

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Products from enzyme-catalyzed oxidations of norcarenes. Abstract Text:

Martin Newcomb,Dharmika S P Lansakara-P,Hye-Yeong Kim,R Esala P Chandrasena,Stephen J Lippard,Laurance G Beauvais,Leslie J Murray,Viviana Izzo,Paul F Hollenberg,Minor J Coon,

Recent studies revealed that norcarane (bicyclo[4.1.0]heptane) is oxidized to 2-norcarene (bicyclo[4.1.0]-hept-2-ene) and 3-norcarene (bicyclo[4.1.0]hept-3-ene) by iron-containing enzymes and that secondary oxidation products from the norcarenes complicate mechanistic probe studies employing norcarane as the substrate (Newcomb, M.; Chandrasena, R. E. P.; Lansakara-P., D. S. P.; Kim, H.-Y.; Lippard, S. J.; Beauvais, L. G.; Murray, L. J.; Izzo, V.; Hollenberg, P. F.; Coon, M. J. J. Org. Chem. 2007, 72, 1121-1127). In the present work, the product profiles from the oxidations of 2-norcarene and 3-norcarene by several enzymes were determined. Most of the products were identified by GC and GC-mass spectral comparison to authentic samples produced independently; in some cases, stereochemical assignments were made or confirmed by 2D NMR analysis of the products. The enzymes studied in this work were four cytochrome P450 enzymes, CYP2B1, CYPDelta2E1, CYPDelta2E1 T303A, and CYPDelta2B4, and three diiron-containing enzymes, soluble methane monooxygenase (sMMO) from Methylococcus capsulatus (Bath), toluene monooxygenase (ToMO) from Pseudomonas stutzeri OX1, and phenol hydroxylase (PH) from Pseudomonas stutzeri OX1. The oxidation products from the norcarenes identified in this work are 2-norcaranone, 3-norcaranone, syn- and anti-2-norcarene oxide, syn- and anti-3-norcarene oxide, syn- and anti-4-hydroxy-2-norcarene, syn- and anti-2-hydroxy-3-norcarene, 2-oxo-3-norcarene, 4-oxo-2-norcarene, and cyclohepta-3,5-dienol. Two additional, unidentified oxidation products were observed in low yields in the oxidations. In matched oxidations, 3-norcarene was a better substrate than 2-norcarene in terms of turnover by factors of 1.5-15 for the enzymes studied here. The oxidation products found in enzyme-catalyzed oxidations of the norcarenes are useful for understanding the complex product mixtures obtained in norcarane oxidations.

Products from enzyme-catalyzed oxidations of norcarenes. Publishing Authors By Initials

M Newcomb,DS Lansakara-P,HY Kim,RE Chandrasena,SJ Lippard,LG Beauvais,LJ Murray,V Izzo,PF Hollenberg,MJ Coon,

For similar organic chemicals: hydrocarbons: terpenes research abstracts see: organic chemicals: hydrocarbons: terpenes research

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Products from enzyme-catalyzed oxidations of norcarenes. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: The Journal of organic chemistry

VOLUME: 72

Page Numbers: 1128-33

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 16

MONTH: Feb

YEAR: 2007

Products from enzyme-catalyzed oxidations of norcarenes. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 2985193

Products from enzyme-catalyzed oxidations of norcarenes. Keywords Mesh Terms:

KEYWORDS: Terpenes

MESH TERMS: metabolism

Chemical & Substance for Abstract: Products from enzyme-catalyzed oxidations of norcarenes. Information

Substance Name: phenol 2-monooxygenase

Registry Number: EC 1.14.13.7

Grant and Affiliation Information for Products from enzyme-catalyzed oxidations of norcarenes.

AFFILIATION: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA. men@uic.edu

Country: United States

AGENCY: United States NIGMS

GRANT: GM 48722

ACRONYM: GM

MEDLINETA: J Org Chem

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