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Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 10, p. 3138-3142Article in journal (Refereed) Published
Abstract [en]

Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019. Vol. 58, no 10, p. 3138-3142
Keywords [en]
alkenes, amino alcohols, biocatalysis, directed evolution, heme proteins, nitrenes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-246489DOI: 10.1002/anie.201812968ISI: 000459709300031PubMedID: 30600873Scopus ID: 2-s2.0-85060639831OAI: oai:DiVA.org:kth-246489DiVA, id: diva2:1299663
Note

QC 20190328

Available from: 2019-03-28 Created: 2019-03-28 Last updated: 2019-03-28Bibliographically approved

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Görbe, Tamás

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