Biotransformation of Dibenzylbutanolides by Peroxidase Enzymes. Routes to the Podophyllotoxin Family.

Kutney, James P.; Du, Xinyao; Naidu, R; Stoynov, Nikolay; Takemoto, Masumi

doi:10.3987/com-95-s65

Cited by 16 publications

(1 citation statement)

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“…Although the reaction worked also in hexane, quantitative ring closure only occurred when the reaction was done in B5 medium [153,154]. A similar reaction, but with H 2 O 2 as a cofactor and ethanol as solvent, has also been reported on the same lignan [155].…”

Section: Other Oxidation Methodsmentioning

confidence: 99%

Oxidative Transformations of Lignans

Runeberg¹,

Brusentsev²,

Rendon³

et al. 2019

Molecules

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Numerous oxidative transformations of lignan structures have been reported in the literature. In this paper we present an overview on the current findings in the field. The focus is put on transformations targeting a specific structure, a specific reaction, or an interconversion of the lignan skeleton. Oxidative transformations related to biosynthesis, antioxidant measurements, and total syntheses are mostly excluded. Non-metal mediated as well as metal mediated oxidations are reported, and mechanisms based on hydrogen abstractions, epoxidations, hydroxylations, and radical reactions are discussed for the transformation and interconversion of lignan structures. Enzymatic oxidations, photooxidation, and electrochemical oxidations are also briefly reported.

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Section: Other Oxidation Methodsmentioning

confidence: 99%

Oxidative Transformations of Lignans

Runeberg¹,

Brusentsev²,

Rendon³

et al. 2019

Molecules

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Chemoenzymatische Totalsynthese von Deoxy‐, epi‐ und Podophyllotoxin sowie biokatalytische kinetische Racematspaltung von Dibenzylbutyrolactonen

et al. 2019

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Podophyllotoxin (1)i st einer der bekanntesten Vertreter von natürlich vorkommenden Lignanen. Deoxy-, epiund Podophyllotoxin, welche alle Vorstufen fürh äufig verwendete chemotherapeutische Verbindungen darstellen, wurden mithilfe einer stereodivergenten Biotransformation und biokatalytischen kinetischen Racematspaltung der jeweiligen Dibenzylbutyrolactone durch dieselbe 2-Oxoglutaratabhängige Dioxygenase( 2-ODD) hergestellt. Zudem konnte gezeigt werden, dass ein "Upscaling" der Reaktion auf 2g mçglich ist, sowied ass das 2-ODD-Enzym Modifikationen des "natürlichen" Substrates toleriert und somit verschiedenste nichtnatürlicheD erivate umsetzen kann. Das Enzym führt je nachS ubstituentenmuster entweder eine oxidative C-C-Bindungsbildung durch C-H-Aktivierung oder Hydroxylierung an der fürdie Ringschließung zugänglichen benzylischen Position durch.

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Chemoenzymatic Total Synthesis of Deoxy‐, epi‐, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

et al. 2019

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Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy‐, epi ‐, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2‐oxoglutarate‐dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non‐natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C−C bond formation by C−H activation or hydroxylation at the benzylic position prone to ring closure.

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Biotransformation of Dibenzylbutanolides by Peroxidase Enzymes. Routes to the Podophyllotoxin Family.

Cited by 16 publications

References 0 publications

Oxidative Transformations of Lignans

Oxidative Transformations of Lignans

Chemoenzymatische Totalsynthese von Deoxy‐, epi‐ und Podophyllotoxin sowie biokatalytische kinetische Racematspaltung von Dibenzylbutyrolactonen

Chemoenzymatic Total Synthesis of Deoxy‐, epi‐, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

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