Novel concurrent redox cascades of (R)- and (S)-carvones enables access to carvo-lactones with distinct regio- and enantioselectivity

Naseem Iqbal, Jon D. Stewart, Peter Macheroux, Florian Rudroff, Marko D. Mihovilovic

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Abstract

Within this study, we investigated a one-pot enzymatic redox cascade composed of different enoate reductases (5 EREDs from diverse bacterial origins) and various Baeyer-Villiger monooxygenases (4 BVMOs) with complementary regioselectivity that enabled access to six out of eight carvo-lactone stereoisomers starting from readily available natural carvones. Applicability of this two-step cascade was demonstrated by preparative scale experiments yielding up to 76% of the desired chiral carvolactone.

Originalspracheenglisch
Seiten (von - bis)7389-7394
Seitenumfang6
FachzeitschriftTetrahedron
Jahrgang74
Ausgabenummer52
DOIs
PublikationsstatusVeröffentlicht - 27 Dez 2018

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Regioselectivity
Stereoisomerism
Enantioselectivity
Lactones
Mixed Function Oxygenases
Oxidation-Reduction
Oxidoreductases
Experiments
carvone

Schlagwörter

    ASJC Scopus subject areas

    • !!Biochemistry
    • !!Drug Discovery
    • Organische Chemie

    Dies zitieren

    Novel concurrent redox cascades of (R)- and (S)-carvones enables access to carvo-lactones with distinct regio- and enantioselectivity. / Iqbal, Naseem; Stewart, Jon D.; Macheroux, Peter; Rudroff, Florian; Mihovilovic, Marko D.

    in: Tetrahedron, Jahrgang 74, Nr. 52, 27.12.2018, S. 7389-7394.

    Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

    Iqbal, Naseem ; Stewart, Jon D. ; Macheroux, Peter ; Rudroff, Florian ; Mihovilovic, Marko D. / Novel concurrent redox cascades of (R)- and (S)-carvones enables access to carvo-lactones with distinct regio- and enantioselectivity. in: Tetrahedron. 2018 ; Jahrgang 74, Nr. 52. S. 7389-7394.
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    AU - Stewart, Jon D.

    AU - Macheroux, Peter

    AU - Rudroff, Florian

    AU - Mihovilovic, Marko D.

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    KW - Biotransformation

    KW - Carvone

    KW - Cascade reaction

    KW - Eonate reductase

    KW - Redox enzymes

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