P450-catalyzed regio- and stereoselective oxidative hydroxylation of 
disubstituted cyclohexanes: creation of three centers of chirality in a single 
CH-activation event

Ilie, Adriana; Agudo Torres, Rubén; Roiban, Georghe-Doru; Reetz, Manfred T.

doi:10.1016/j.tet.2014.11.067

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P450-catalyzed regio- and stereoselective oxidative hydroxylation of disubstituted cyclohexanes: creation of three centers of chirality in a single CH-activation event

Ilie, A., Agudo Torres, R., Roiban, G.-D., & Reetz, M. T. (2015). P450-catalyzed regio- and stereoselective oxidative hydroxylation of disubstituted cyclohexanes: creation of three centers of chirality in a single CH-activation event. Tetrahedron, 71(3), 470-475. doi:10.1016/j.tet.2014.11.067.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-B958-4 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-B959-2

Genre: Journal Article

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Creators:
Ilie, Adriana^{1, 2}, Author
Agudo Torres, Rubén^{1, 2}, Author
Roiban, Georghe-Doru^{1, 2}, Author
Reetz, Manfred T.^{1, 2}, Author

Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588
2Philipps-Universität Marburg, Fachbereich Chemie, ou_persistent22

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Abstract: Wild-type P450-BM3 is able to catalyze in a highly regio- and diastereoselective manner the oxidative hydroxylation of non-activated disubstituted cyclohexane derivatives lacking any functional groups, including cis- and trans-1,2-dimethylcyclohexane, cis- and trans-1,4-dimethylcyclohexane, and trans-1,4-methylisopropylcyclohexane. In all cases except chiral trans-1,2-dimethylcyclohexane as substrate, the single hydroxylation event at a methylene group induces desymmetrization with simultaneous creation of three centers of chirality. Certain mutants increase selectivity, setting the stage for future directed evolution work.

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Language(s): eng - English

Dates: Submitted: 2014-09-07Accepted: 2014-11-26Published Online: 2014-12-02Date issued: 2015-01-25

Publication Status: Issued

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Rev. Type: Peer

Identifiers: DOI: 10.1016/j.tet.2014.11.067

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Title: Tetrahedron

Other : Tetrahedron

Source Genre: Journal

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Pages: - Volume / Issue: 71 (3) Sequence Number: - Start / End Page: 470 - 475 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773