Stereodivergent Biocatalytic Formal Reduction of α‐Angelica Lactone to (R)‐ and (S)‐γ‐Valerolactone in a One‐Pot Cascade
Abstract: The formal asymmetric and stereodivergent enzymatic reduction of α‐angelica lactone to both enantiomers of γ‐valerolactone was achieved in a one‐pot cascade by uniting the promiscuous stereoselective isomerization activity of Old Yellow Enzymes with their native reductase activity. In addition to running the cascade with one enzyme for each catalytic step, a bifunctional isomerase‐reductase biocatalyst was designed by fusing two Old Yellow Enzymes, thereby generating an unprecedented case of an artificial enzyme catalyzing the reduction of nonactivated C=C bonds to access (R)‐valerolactone in overall 41 % conversion and up to 91 % ee. The enzyme BfOYE4 could be used as single biocatalyst for both steps and delivered (S)‐valerolactone in up to 84 % ee and 41 % overall conversion. The reducing equivalents were provided by a nicotinamide recycling system based on formate and formate dehydrogenase, added in a second step. This enzymatic system provides an asymmetric route to valuable chiral building blocks from an abundant bio‐based chemical.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Stereodivergent Biocatalytic Formal Reduction of α‐Angelica Lactone to (R)‐ and (S)‐γ‐Valerolactone in a One‐Pot Cascade ; day:04 ; month:04 ; year:2023 ; extent:8
ChemBioChem ; (04.04.2023) (gesamt 8)
- Urheber
-
Tonoli, Alessia
Wagner, Karla
Bacchin, Arianna
Reiter, Tamara
Bergantino, Elisabetta
Robescu, Marina S.
Hall, Mélanie
- DOI
-
10.1002/cbic.202300146
- URN
-
urn:nbn:de:101:1-2023040415284100810725
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 10:49 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Tonoli, Alessia
- Wagner, Karla
- Bacchin, Arianna
- Reiter, Tamara
- Bergantino, Elisabetta
- Robescu, Marina S.
- Hall, Mélanie
Ähnliche Objekte (12)
A One-Pot Biocatalytic Sequence to 6-Aminohexanoic Acid
Die One-Pot Challenge
Advanced one-pot deconstruction and valorization of lignocellulosic biomass into triacetic acid lactone using Rhodosporidium toruloides
One‐Pot Synthesis of Chiral N ‐Arylamines by Combining Biocatalytic Aminations with Buchwald–Hartwig N ‐Arylation
Three-steps in one-pot: whole-cell biocatalytic synthesis of enantiopure (+)- and (−)-pinoresinol via kinetic resolution
One‐Pot Synthesis of Thiocarbamates
One-Pot Synthesis of Cycloparaphenylenes
PQQ‐dependent Dehydrogenase Enables One‐pot Bi‐enzymatic Enantio‐convergent Biocatalytic Amination of Racemic sec ‐Allylic Alcohols
Stereoselective one-pot synthesis of polypropionates
One-pot synthesis of (R)- and (S)-phenylglycinol from bio-based l-phenylalanine by an artificial biocatalytic cascade
Pot-Economic Organocatalytic Asymmetric Synthesis of the Corey Lactone
One‐Pot Biocatalytic In Vivo Methylation‐Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L‐DOPA
A One-Pot Biocatalytic Sequence to 6-Aminohexanoic Acid
Die One-Pot Challenge
Advanced one-pot deconstruction and valorization of lignocellulosic biomass into triacetic acid lactone using Rhodosporidium toruloides
One‐Pot Synthesis of Chiral N ‐Arylamines by Combining Biocatalytic Aminations with Buchwald–Hartwig N ‐Arylation
Three-steps in one-pot: whole-cell biocatalytic synthesis of enantiopure (+)- and (−)-pinoresinol via kinetic resolution
One‐Pot Synthesis of Thiocarbamates
One-Pot Synthesis of Cycloparaphenylenes
PQQ‐dependent Dehydrogenase Enables One‐pot Bi‐enzymatic Enantio‐convergent Biocatalytic Amination of Racemic sec ‐Allylic Alcohols
Stereoselective one-pot synthesis of polypropionates
One-pot synthesis of (R)- and (S)-phenylglycinol from bio-based l-phenylalanine by an artificial biocatalytic cascade
Pot-Economic Organocatalytic Asymmetric Synthesis of the Corey Lactone
One‐Pot Biocatalytic In Vivo Methylation‐Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L‐DOPA
A One-Pot Biocatalytic Sequence to 6-Aminohexanoic Acid
Die One-Pot Challenge
Advanced one-pot deconstruction and valorization of lignocellulosic biomass into triacetic acid lactone using Rhodosporidium toruloides
One‐Pot Synthesis of Chiral N ‐Arylamines by Combining Biocatalytic Aminations with Buchwald–Hartwig N ‐Arylation
Three-steps in one-pot: whole-cell biocatalytic synthesis of enantiopure (+)- and (−)-pinoresinol via kinetic resolution
One‐Pot Synthesis of Thiocarbamates
One-Pot Synthesis of Cycloparaphenylenes
PQQ‐dependent Dehydrogenase Enables One‐pot Bi‐enzymatic Enantio‐convergent Biocatalytic Amination of Racemic sec ‐Allylic Alcohols
Stereoselective one-pot synthesis of polypropionates
One-pot synthesis of (R)- and (S)-phenylglycinol from bio-based l-phenylalanine by an artificial biocatalytic cascade
Pot-Economic Organocatalytic Asymmetric Synthesis of the Corey Lactone