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Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein
Vise andre og tillknytning
2019 (engelsk)Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, nr 10, s. 3138-3142Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
Wiley-VCH Verlagsgesellschaft, 2019. Vol. 58, nr 10, s. 3138-3142
Emneord [en]
alkenes, amino alcohols, biocatalysis, directed evolution, heme proteins, nitrenes
HSV kategori
Identifikatorer
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
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QC 20190328

Tilgjengelig fra: 2019-03-28 Laget: 2019-03-28 Sist oppdatert: 2019-03-28bibliografisk kontrollert

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