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Stereoselective Friedel-Crafts alkylation catalyzed by squalene hopene cyclases
Universitaet Stuttgart, Germany.ORCID iD: 0000-0002-4066-2776
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2012 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no Copyright (C) 2013 American Chemical Society (ACS). All Rights Reserved., 7624-7629 p.Article in journal (Refereed) Published
Abstract [en]

In org. synthesis the Friedel-Crafts alkylation is of eminent importance, as it is a key reaction in many synthetic routes. A general access to enzymic Friedel-Crafts alkylations would be very beneficial due to the high selectivity of biocatalysts. We used designed polyprenyl Ph ethers to specifically address this reaction by using squalene hopene cyclases as catalysts. Polycyclic products with arom. rings constituting important biol. active compds. were obtained. Our results demonstrate that squalene hopene cyclases can be utilized for Friedel-Crafts alkylations and reveal the potential of these enzymes for chiral Bronsted acid catalysis.

Place, publisher, year, edition, pages
Elsevier Ltd. , 2012. Vol. 68, no Copyright (C) 2013 American Chemical Society (ACS). All Rights Reserved., 7624-7629 p.
Keyword [en]
Friedel Crafts alkylation catalyzed squalene hopene cyclase
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:kth:diva-185570DOI: 10.1016/j.tet.2012.06.041ISI: 000307802300015ScopusID: 2-s2.0-84864432284OAI: oai:DiVA.org:kth-185570DiVA: diva2:922314
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QC 20160429

Available from: 2016-04-22 Created: 2016-04-22 Last updated: 2016-04-29Bibliographically approved

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Syren, Per-Olof
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